text: Note, the O3 and O4 atoms are both associated with axial hydroxyl groups pointed in opposite direction and separated by the single carbon-carbon bond of C3 and C4.  The angles between the carbon-hydroxyl group bonds and the carbon-carbon bond are nominally 109.5 degrees.

text: Note, the O3 and O4 atoms are both associated with axial hydroxyl groups pointed in opposite direction and separated by the single carbon-carbon bond of C3 and C4.  The angles between the carbon-hydroxyl group bonds and the carbon-carbon bond are nominally 109.5 degrees.

method: UNH-tfidf-stem

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answer_match: Using FLAN-T5-Large with this prompt: For the question "{question}" the correct answer is "{correct_answer}". Is "{answer}" an equally correct response to this question? Answer yes or no.

prompt_style: provide a complete and concise answer to the question based on the context.

text: Staffanes were first obtained in 1988 by P. Kazynski and J. Michl, by spontaneous polymerization of [1.1.1]-propellane CH or C(=CH).  In the reaction, the axial C-C bond of the propellane (the "bridge") is broken, creating a free bond on each of the two axial carbons (the "bridgeheads").  The resulting structural unit [-C≡(-CH-)≡C-] is a rigid cage, consisting of two carbon atoms joined by three methylene bridges; therefore the joined units are constrained to lie on a straight line.  This feature has generated substantial interest among nanotechnology researchers, who have considered staffane oligomers as convenient "rigid rods" for building all sorts of nanostructures.

text: Staffanes were first obtained in 1988 by

text: P. Kazynski

text: and

text: J. Michl

text: , by spontaneous

entity_name: Polymerization

text: polymerization

text: of

text: CH or C(=CH).  In the reaction, the axial C-C bond of the propellane (the "bridge") is broken, creating a free bond on each of the two axial

entity_name: Carbon

text: carbon

text: s (the "bridgeheads").  The resulting structural unit [-C≡(-CH-)≡C-] is a rigid cage, consisting of two carbon atoms joined by three

entity_name: Methylene bridge

text: methylene bridge

text: s; therefore the joined units are constrained to lie on a straight line.  This feature has generated substantial interest among

entity_name: Nanotechnology

text: nanotechnology

text: researchers, who have considered staffane oligomers as convenient "rigid rods" for building all sorts of nanostructures.

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answers: [1.1.1]-propellane

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answers: [1.1.1]-propellane CH

text: The mechanism of the Wolff–Kishner reduction has been studied by Szmant and coworkers. According to Szmant's research, the first step in this reaction is the formation of a hydrazone anion 1 by deprotonation of the terminal nitrogen by MOH. If semicarbazones are used as substrates, initial conversion into the corresponding hydrazone is followed by deprotonation. A range of mechanistic data suggests that the rate-determining step involves formation of a new carbon–hydrogen bond at the carbon terminal in the delocalized hydrazone anion. This proton capture takes place in a concerted fashion with a solvent-induced abstraction of the second proton at the nitrogen terminal. Szmant’s finding that this reaction is first order in both hydroxide ion and ketone hydrazone supports this mechanistic proposal. Several molecules of solvent have to be involved in this process in order to allow for a concerted process. A detailed Hammett analysis of aryl aldehydes, methyl aryl ketones and diaryl ketones showed a non-linear relationship which the authors attribute to the complexity of the rate-determining step. Mildy electron-withdrawing substituents favor carbon-hydrogen bond formation, but highly electron-withdrawing substitutents will decrease the negative charge at the terminal nitrogen and in turn favor a bigger and harder solvation shell that will render breaking of the N-H bond more difficult. The exceptionally high negative entropy of activation values observed can be explained by the high degree of organization in the proposed transition state.

text: The mechanism of the Wolff–Kishner reduction has been studied by Szmant and coworkers. According to Szmant's research, the first step in this reaction is the formation of a hydrazone anion 1 by deprotonation of the terminal nitrogen by MOH. If

entity_name: Semicarbazone

text: semicarbazones

text: are used as substrates, initial conversion into the corresponding hydrazone is followed by deprotonation. A range of mechanistic data suggests that the

entity_name: Rate-determining step

text: rate-determining step

text: involves formation of a new carbon–hydrogen bond at the carbon terminal in the delocalized hydrazone anion. This proton capture takes place in a concerted fashion with a solvent-induced abstraction of the second proton at the nitrogen terminal. Szmant’s finding that this reaction is first order in both hydroxide ion and ketone hydrazone supports this mechanistic proposal. Several molecules of solvent have to be involved in this process in order to allow for a concerted process. A detailed

entity_name: Hammett equation

text: Hammett analysis

text: of aryl aldehydes, methyl aryl ketones and diaryl ketones showed a non-linear relationship which the authors attribute to the complexity of the rate-determining step. Mildy electron-withdrawing substituents favor carbon-hydrogen bond formation, but highly electron-withdrawing substitutents will decrease the negative charge at the terminal nitrogen and in turn favor a bigger and harder solvation shell that will render breaking of the N-H bond more difficult. The exceptionally high negative entropy of activation values observed can be explained by the high degree of organization in the proposed transition state.

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answers: Carbon–hydrogen bond

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text: Addition reactions are limited to chemical compounds that have multiple bonds, such as molecules with carbon-carbon double bonds (alkenes), or with triple bonds (alkynes). Molecules containing carbon—hetero double bonds like carbonyl (C=O) groups, or imine (C=N) groups, can undergo addition as they too have double bond character.

text: Addition reactions are limited to chemical compounds that have multiple bonds, such as molecules with carbon-carbon

entity_name: Double bond

text: double bond

text: s (

entity_name: Alkene

text: alkene

text: s), or with

entity_name: Triple bond

text: triple bond

text: s (

entity_name: Alkyne

text: alkyne

text: s). Molecules containing carbon—

entity_name: Heteroatom

text: hetero

text: double bonds like

entity_name: Carbonyl group

text: carbonyl

text: (C=O) groups, or

entity_name: Imine

text: imine

text: (C=N) groups, can undergo addition as they too have double bond character.

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text: Tetrahedrane is a platonic hydrocarbon with chemical formula  and a tetrahedral structure. Extreme  angle strain (carbon bond angles deviate considerably from the tetrahedral bond angle of 109.5°) prevents this molecule from forming naturally.

text: Tetrahedrane is a

entity_name: Platonic hydrocarbon

text: platonic hydrocarbon

text: with

entity_name: Chemical formula

text: chemical formula

text: and a

entity_name: Tetrahedron

text: tetrahedral

text: structure. Extreme

entity_name: Ring strain

text: angle strain

text: (carbon bond angles deviate considerably from the tetrahedral bond angle of 109.5°) prevents this molecule from forming naturally.

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answers: 109.5°

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answers: Tetrahedrane

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answers: Tetrahedrane

text: In chemical bonds, an orbital overlap is the concentration of orbitals on adjacent atoms in the same regions of space.  Orbital overlap can lead to bond formation. The importance of orbital overlap was emphasized by Linus Pauling to explain the molecular bond angles observed through experimentation and is the basis for the concept of orbital hybridization.  Since s orbitals are spherical (and have no directionality) and p orbitals are oriented 90° to each other, a theory was needed to explain why molecules such as methane (CH) had observed bond angles of 109.5°.  Pauling proposed that s and p orbitals on the carbon atom  can combine to form hybrids (sp in the case of methane) which are directed toward the hydrogen atoms. The carbon hybrid orbitals have greater overlap with the hydrogen orbitals, and can therefore form stronger C–H bonds.

text: In

entity_name: Chemical bond

text: chemical bond

text: s, an orbital overlap is the concentration of orbitals on adjacent atoms in the same regions of space.  Orbital overlap can lead to bond formation. The importance of orbital overlap was emphasized by

entity_name: Linus Pauling

text: Linus Pauling

text: to explain the molecular

entity_name: Molecular geometry

text: bond angle

text: s observed through experimentation and is the basis for the concept of

entity_name: Orbital hybridisation

text: orbital hybridization

text: .  Since s orbitals are spherical (and have no directionality) and p orbitals are oriented 90° to each other, a theory was needed to explain why molecules such as

entity_name: Methane

text: methane

text: (CH) had observed bond angles of 109.5°.  Pauling proposed that s and p orbitals on the carbon atom  can combine to form hybrids (sp in the case of methane) which are directed toward the hydrogen atoms. The carbon hybrid orbitals have greater overlap with the hydrogen orbitals, and can therefore form stronger C–H bonds.

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answers: methane

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answers: methane

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answers: H

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answers: C–H bonds

text: The nucleophilic carbon of the alkyl anion then displaces the halide in an S2 reaction, forming a new carbon-carbon covalent bond.

text: The nucleophilic carbon of the alkyl anion then displaces the halide in an

entity_name: SN2 reaction

text: S2 reaction

text: , forming a new carbon-carbon covalent bond.

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text: Carbon introduction through the opening of a bicyclic system is way to introduce either a single carbon or several at a time to the ring. The single carbon introduction often goes through a cyclopropane containg bicyclic intermediate, which is then opened to give the expanded ring. The expansion can occur either through an electrocylic ring opening or an induced cleavage of the shared bond. These reactions are differentiated in terms of how the carbon is added to form the cyclopropane ring. A Simmons-Smith like reaction with an alkene containing ring can be used to introduce a single carbon. Other methods exist to cyclopropantate other functionalities, such as the Buchner ring expansion for arenes.

text: Carbon introduction through the opening of a

entity_name: Bicyclic molecule

text: bicyclic system

text: is way to introduce either a single carbon or several at a time to the ring. The single carbon introduction often goes through a

entity_name: Cyclopropane

text: cyclopropane

text: containg bicyclic intermediate, which is then opened to give the expanded ring. The expansion can occur either through an electrocylic ring opening or an induced cleavage of the shared bond. These reactions are differentiated in terms of how the carbon is added to form the cyclopropane ring. A

entity_name: Simmons–Smith reaction

text: Simmons-Smith

text: like reaction with an alkene containing ring can be used to introduce a single carbon. Other methods exist to cyclopropantate other functionalities, such as the

entity_name: Buchner ring expansion

text: Buchner ring expansion

text: for

entity_name: Aromatic hydrocarbon

text: arenes

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answers: Carbon

text: In a prelude to the actual Shapiro reaction a ketone or an aldehyde is reacted with p-toluenesulfonylhydrazide to a p-toluenesulfonylhydrazone (or tosylhydrazone) which is an imine or hydrazone. Two equivalents of a strong base, such as n-butyllithium, then abstract first the proton from the hydrazone  and then the less acidic proton α to the hydrazone carbon, leaving a carbanion. The carbanion proceeds in an elimination reaction to create the carbon–carbon double bond. This step results in expulsion of the tosyl group and formation of a diazonium anion. The anion then collapses, falling off as a neutral nitrogen molecule. The result is a vinyllithium at the position where the nitrogen had been attached. This organolithium carbon is both nucleophilic and basic. It can be reacted with various electrophiles or simply neutralized with water or an acid.

text: In a prelude to the actual Shapiro reaction a

entity_name: Ketone

text: ketone

text: or an

entity_name: Aldehyde

text: aldehyde

text: is reacted with

entity_name: Hydrazide

text: p-toluenesulfonylhydrazide

text: to a p-toluenesulfonylhydrazone (or

entity_name: Tosylhydrazone

text: tosylhydrazone

text: ) which is an

text: imine

text: or

entity_name: Hydrazone

text: hydrazone

text: . Two equivalents of a strong

entity_name: Base (chemistry)

text: base

text: , such as

entity_name: N-Butyllithium

text: n-butyllithium

text: , then abstract first the

entity_name: Hydron (chemistry)

text: proton

text: from the hydrazone  and then the less

entity_name: Carbanion

entity_section: Carbon acids

text: acidic

text: proton α to the hydrazone carbon, leaving a

text: carbanion

text: . The carbanion proceeds in an

entity_name: Elimination reaction

text: elimination reaction

text: to create the carbon–carbon

text: double bond

text: . This step results in expulsion of the

entity_name: Tosyl

text: tosyl group

text: and formation of a

entity_name: Diazonium compound

text: diazonium

text: anion. The anion then collapses, falling off as a neutral

entity_name: Nitrogen

text: nitrogen molecule

text: . The result is a

entity_name: Vinyl group

text: vinyl

text: lithium at the position where the nitrogen had been attached. This

entity_name: Organolithium reagent

text: organolithium

text: carbon is both

entity_name: Nucleophile

text: nucleophilic

text: and

text: basic

text: . It can be reacted with various

entity_name: Electrophile

text: electrophile

text: s or simply neutralized with water or an acid.

method: Bert-DRMMTKS

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answers: carbon–carbon double bond

text: There can also be off-resonance decoupling of H from C nuclei in C NMR spectroscopy, where weaker rf irradiation results in what can be thought of as partial decoupling.  In such an off-resonance decoupled spectrum, only H atoms bonded to a carbon atom will split its C signal.  The coupling constant, indicating a small frequency difference between split signal peaks, would be smaller than in an undecoupled spectrum.  Looking at a compound's off-resonance proton-decoupled C spectrum can show how many hydrogens are bonded to the carbon atoms to further help elucidate the chemical structure.  For most organic compounds, carbons bonded to 3 hydrogens (methyls) would appear as quartets (4-peak signals), carbons bonded to 2 equivalent hydrogens would appear as triplets (3-peak signals), carbons bonded to 1 hydrogen would be doublets (2-peak signals), and carbons not bonded directly to any hydrogens would be singlets (1-peak signals).

text: There can also be off-resonance decoupling of H from C nuclei in C NMR spectroscopy, where weaker rf irradiation results in what can be thought of as partial decoupling.  In such an off-resonance decoupled spectrum, only H atoms bonded to a carbon atom will split its C signal.  The coupling constant, indicating a small frequency difference between split signal peaks, would be smaller than in an undecoupled spectrum.  Looking at a compound's off-resonance proton-decoupled C spectrum can show how many hydrogens are bonded to the carbon atoms to further help

entity_name: Chemical structure

text: elucidate the chemical structure

text: .  For most organic compounds, carbons bonded to 3 hydrogens (

entity_name: Methyl group

text: methyl

text: s) would appear as quartets (4-peak signals), carbons bonded to 2 equivalent hydrogens would appear as triplets (3-peak signals), carbons bonded to 1 hydrogen would be doublets (2-peak signals), and carbons not bonded directly to any hydrogens would be singlets (1-peak signals).

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text: X-ray diffraction shows that all six carbon-carbon bonds in benzene are of the same length, at 140 picometres (pm). The C–C bond lengths are greater than a double bond (135 pm) but shorter than a single bond (147 pm). This intermediate distance is consistent with electron delocalization: the electrons for C–C bonding are distributed equally between each of the six carbon atoms. Benzene has 6 hydrogen atoms – fewer than the corresponding parent alkane, hexane. The molecule is planar. The MO description involves the formation of three delocalized π orbitals spanning all six carbon atoms, while the VB description involves a superposition of resonance structures. It is likely that this stability contributes to the peculiar molecular and chemical properties known as aromaticity. To accurately reflect the nature of the bonding, benzene is often depicted with a circle inside a hexagonal arrangement of carbon atoms.

entity_name: X-ray crystallography

text: X-ray diffraction

text: shows that all six carbon-carbon bonds in benzene are of the same length, at 140

entity_name: Picometre

text: picometre

text: s (pm). The C–C

entity_name: Bond length

text: bond length

text: s are greater than a double bond (135 pm) but shorter than a single bond (147 pm). This intermediate distance is consistent with electron

entity_name: Delocalized electron

text: delocalization

text: : the electrons for C–C bonding are distributed equally between each of the six carbon atoms. Benzene has 6 hydrogen atoms – fewer than the corresponding parent

entity_name: Alkane

text: alkane

entity_name: Hexane

text: hexane

text: . The molecule is planar. The MO description involves the formation of three delocalized

entity_name: Pi bond

text: π orbitals

text: spanning all six carbon atoms, while the VB description involves a superposition of

entity_name: Resonance (chemistry)

text: resonance structures

text: . It is likely that this stability contributes to the peculiar molecular and chemical properties known as

entity_name: Aromaticity

text: aromaticity

text: . To accurately reflect the nature of the bonding, benzene is often depicted with a circle inside a hexagonal arrangement of carbon atoms.

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text: There are several methods of producing DLC, which rely on the lower density of sp than sp carbon. So the application of pressure, impact, catalysis, or some combination of these at the atomic scale can force sp bonded carbon atoms closer together into sp bonds. This must be done vigorously enough that the atoms cannot simply spring back apart into separations characteristic of sp bonds. Usually techniques either combine such a compression with a push of the new cluster of sp bonded carbon deeper into the coating so that there is no room for expansion back to separations needed for sp bonding; or the new cluster is buried by the arrival of new carbon destined for the next cycle of impacts. It is reasonable to envisage the process as a "hail" of projectiles that produce localized, faster, nanoscale versions of the classic combinations of heat and pressure that produce natural and synthetic diamond. Because they occur independently at many places across the surface of a growing film or coating, they tend to produce an analog of a cobblestone street with the cobbles being nodules or clusters of sp bonded carbon. Depending upon the particular "recipe" being used, there are cycles of deposition of carbon and impact or continuous proportions of new carbon arriving and projectiles conveying the impacts needed to force the formation of the sp bonds. As a result, ta-C may have the structure of a cobblestone street, or the nodules may "melt together" to make something more like a sponge or the cobbles may be so small as to be nearly invisible to imaging. A classic "medium" morphology for a ta-C film is shown in the figure.

text: There are several methods of producing DLC, which rely on the lower density of sp than sp carbon. So the application of pressure, impact,

entity_name: Catalysis

text: catalysis

text: , or some combination of these at the atomic scale can force sp bonded carbon atoms closer together into sp bonds. This must be done vigorously enough that the atoms cannot simply spring back apart into separations characteristic of sp bonds. Usually techniques either combine such a compression with a push of the new cluster of sp bonded carbon deeper into the coating so that there is no room for expansion back to separations needed for sp bonding; or the new cluster is buried by the arrival of new carbon destined for the next cycle of impacts. It is reasonable to envisage the process as a "hail" of projectiles that produce localized, faster,

text: nanoscale

text: versions of the classic combinations of heat and pressure that produce natural and synthetic diamond. Because they occur independently at many places across the surface of a growing film or coating, they tend to produce an analog of a

entity_name: Cobblestone

text: cobblestone

text: street with the cobbles being nodules or clusters of sp bonded carbon. Depending upon the particular "recipe" being used, there are cycles of deposition of carbon and impact or continuous proportions of new carbon arriving and projectiles conveying the impacts needed to force the formation of the sp bonds. As a result, ta-C may have the structure of a cobblestone street, or the nodules may "melt together" to make something more like a

entity_name: Sponge

text: sponge

text: or the cobbles may be so small as to be nearly invisible to imaging. A classic "medium" morphology for a ta-C film is shown in the figure.

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text: Transition metal carbyne complexes are organometallic compounds with a triple bond between carbon and the transition metal. This triple bond consists of a σ-bond and two π-bonds. The HOMO of the carbyne ligand interacts with the LUMO of the metal to create the σ-bond. The two π-bonds are formed when the two HOMO orbitals of the metal back-donate to the LUMO of the carbyne. They are also called metal alkylidynes—the carbon is a carbyne ligand. Such compounds are useful in organic synthesis of alkynes and nitriles. They have been the focus on much fundamental research.

text: Transition metal carbyne complexes are

text: organometallic compound

text: s with a

text: triple bond

text: between carbon and the

text: transition metal

text: . This triple bond consists of a

text: σ-bond

text: and two

text: π-bonds

text: . The

text: HOMO

text: of the carbyne ligand interacts with the

text: LUMO

text: of the metal to create the σ-bond. The two π-bonds are formed when the two HOMO orbitals of the metal

text: back-donate

text: to the LUMO of the carbyne. They are also called metal alkylidynes—the carbon is a

text: carbyne

text: ligand. Such compounds are useful in

text: organic synthesis

text: of

text: alkyne

text: s and

text: nitrile

text: s. They have been the focus on much fundamental research.

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text: Relative to most bonds, a carbon–carbon bond is very strong.

text: Relative to most bonds, a carbon–carbon bond is very strong.

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answers: carbon–carbon bond

text: Decamethylrhodocenium tetrafluoroborate can be synthesised from the tris(acetone) complex [(η-CMe)Rh(MeCO)](BF) by reaction with pentamethylcyclopentadiene, and the analogous iridium synthesis is also known. Decaisopropylrhodicnium hexafluorophosphate was synthesised in 1,2-dimethoxyethane (solvent) in an unusual one-pot synthesis that involves the formation of 20 carbon–carbon bonds:

text: Decamethylrhodocenium tetrafluoroborate can be synthesised from the tris(acetone) complex [(η-CMe)Rh(MeCO)](BF) by reaction with

text: pentamethylcyclopentadiene

text: , and the analogous iridium synthesis is also known. Decaisopropylrhodicnium hexafluorophosphate was synthesised in

text: solvent

text: ) in an unusual

text: one-pot synthesis

text: that involves the formation of 20

text: carbon–carbon bonds

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracies.

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answers: Decamethylrhodocenium tetrafluoroborate

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answers: carbon–carbon bonds

text: Both COX1 and COX2 (also termed prostaglandin-endoperoxide synthase-1 (PTGS1) and PTGS2, respectively) metabolize arachidonic acid by adding molecular O between carbons 9 and 11 to form an endoperoxide bridge between these two carbons, adding molecular O to carbon 15 to yield a 15-hydroperoxy product, creating a carbon-carbon bond between carbons 8 and 12 to create a cyclopentane ring in the middle of the fatty acid, and in the process making PGG2, a product that has two fewer double bonds than arachidonic acid. The 15-hydrpperoxy residue of PGG2 is then reduced to a 15-hydroxyl residue thereby forming PGH2. PGH2 is the parent prostanoid to all other postanoids. It is metabolized by (see diagram in Prostanoids: a) the Prostaglandin E synthase pathway in which any one of three isozymes, PTGES, PTGES2, or PTGES3, convert PGH2 to PGE2 (subsequent products of this pathway include PGA2 and PGB2 (see Prostanoid); b) PGF synthase which converts PGH2 to PGF2α; c) Prostaglandin D2 synthase which converts PGH2 to PGD2 (subsequent products in this pathway include 15-dPGJ2 (see Cyclopentenone prostaglandin); d) thromboxane synthase which converts PGH2 to TXA2 (subsequent products in this pathway include TXB2); and e) Prostacyclin synthase which converts PGH2 to PGI2 (subsequent products in this pathway include 6-keto-PGFα. These pathways have been shown or in some cases presumed to metabolize eicosapentaenoic acid to eicosanoid analogs of the sited products that have three rather than two double bonds and therefore contain the number 3 in place of 2 attached to their names (e.g. PGE3 instead of PGE2).

text: Both COX1 and COX2 (also termed prostaglandin-endoperoxide synthase-1 (

text: ) and

text: , respectively) metabolize arachidonic acid by adding molecular O between carbons 9 and 11 to form an

text: endoperoxide

text: bridge between these two carbons, adding molecular O to carbon 15 to yield a 15-hydroperoxy product, creating a carbon-carbon bond between carbons 8 and 12 to create a

text: cyclopentane

text: ring in the middle of the fatty acid, and in the process making PGG2, a product that has two fewer double bonds than arachidonic acid. The 15-hydrpperoxy residue of PGG2 is then reduced to a 15-

text: hydroxyl

text: residue thereby forming PGH2. PGH2 is the parent prostanoid to all other postanoids. It is metabolized by (see diagram in

text: Prostanoids

text: : a) the

text: Prostaglandin E synthase

text: pathway in which any one of three

text: isozymes

text: PTGES

text: , or

text: , convert PGH2 to PGE2 (subsequent products of this pathway include PGA2 and PGB2 (see

text: Prostanoid

text: ); b) PGF synthase which converts PGH2 to PGF2α; c)

text: Prostaglandin D2 synthase

text: which converts PGH2 to PGD2 (subsequent products in this pathway include 15-dPGJ2 (see

text: Cyclopentenone prostaglandin

text: ); d)

text: thromboxane synthase

text: which converts PGH2 to TXA2 (subsequent products in this pathway include TXB2); and e)

text: Prostacyclin synthase

text: which converts PGH2 to PGI2 (subsequent products in this pathway include 6-keto-PGFα. These pathways have been shown or in some cases presumed to metabolize eicosapentaenoic acid to eicosanoid analogs of the sited products that have three rather than two double bonds and therefore contain the number 3 in place of 2 attached to their names (e.g. PGE3 instead of PGE2).

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracies.

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text: ) because it is one atom away from the carboxylate group.  In β amino acids, the amino group is bonded to the β carbon (

text: ) because it is one atom away from the carboxylate group.  In β amino acids, the amino group is bonded to the β carbon (

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text: The triple bond is very strong with a bond strength of 839 kJ/mol. The sigma bond contributes 369 kJ/mol, the first pi bond contributes 268 kJ/mol and the second pi-bond of 202 kJ/mol bond strength. Bonding usually discussed in the context of molecular orbital theory, which recognizes the triple bond as arising from overlap of s and p orbitals. In the language of valence bond theory, the carbon atoms in an alkyne bond are sp hybridized: they each have two unhybridized p orbitals and two sp hybrid orbitals. Overlap of an sp orbital from each atom forms one sp–sp sigma bond. Each p orbital on one atom overlaps one on the other atom, forming two pi bonds, giving a total of three bonds. The remaining sp orbital on each atom can form a sigma bond to another atom, for example to hydrogen atoms in the parent acetylene. The two sp orbitals project on opposite sides of the carbon atom.

text: The

text: triple bond

text: is very strong with a

text: bond strength

text: of 839 kJ/mol. The sigma bond contributes 369 kJ/mol, the first pi bond contributes 268 kJ/mol and the second pi-bond of 202 kJ/mol bond strength. Bonding usually discussed in the context of

text: molecular orbital theory

text: , which recognizes the triple bond as arising from overlap of s and p orbitals. In the language of

text: valence bond theory

text: , the carbon atoms in an alkyne bond are

text: sp hybridized

text: : they each have two unhybridized

text: p orbital

text: s and two

text: sp hybrid orbitals

text: . Overlap of an sp orbital from each atom forms one sp–sp

text: sigma bond

text: . Each p orbital on one atom overlaps one on the other atom, forming two

text: pi bond

text: s, giving a total of three bonds. The remaining sp orbital on each atom can form a sigma bond to another atom, for example to hydrogen atoms in the parent acetylene. The two sp orbitals project on opposite sides of the carbon atom.

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text: Though characterization of 2-norbornyl cation crystals may have significantly precluded further debates about its electronic structure, it does not crystallize under any standard conditions. Recently, the crystal structure has been obtained and reported through a creative means: addition of aluminum tribromide to 2-norbornyl bromide in dibromomethane at low temperatures afforded crystals of [][]•. By examining the resulting crystal structure, researchers were able to confirm that the crystalline geometry best supports the case for delocalized bonding in the stable 2-norbornyl cation. Bond lengths between the "bridging" carbon 6 and each of carbons 1 and 2 were found to be slightly longer than typical alkane bonds. According to the non-classical picture, one would expect a bond order between 0 and 1 for these bonds, signifying that this explains the crystal structure well. The bond length between carbons 1 and 2 was reported as being between typical single and double carbon-carbon bond lengths, which agrees with non-classical predictions of a bond order slightly above 1. According to the non-classical picture, one would expect a bond order between zero and one for the first two bonds. Investigators who crystallized the 2-norbornyl cation commented that the cation proved impossible to crystallize unless provided a chemical environment that locked it into one definite orientation.

text: Though characterization of 2-norbornyl cation crystals may have significantly precluded further debates about its electronic structure, it does not crystallize under any standard conditions. Recently, the crystal structure has been obtained and reported through a creative means: addition of aluminum tribromide to 2-norbornyl bromide in dibromomethane at low temperatures afforded crystals of [][]•. By examining the resulting crystal structure, researchers were able to confirm that the crystalline geometry best supports the case for delocalized bonding in the stable 2-norbornyl cation. Bond lengths between the "bridging" carbon 6 and each of carbons 1 and 2 were found to be slightly longer than typical alkane bonds. According to the non-classical picture, one would expect a

text: bond order

text: between 0 and 1 for these bonds, signifying that this explains the crystal structure well. The bond length between carbons 1 and 2 was reported as being between typical single and double carbon-carbon bond lengths, which agrees with non-classical predictions of a bond order slightly above 1. According to the non-classical picture, one would expect a bond order between zero and one for the first two bonds. Investigators who crystallized the 2-norbornyl cation commented that the cation proved impossible to crystallize unless provided a chemical environment that locked it into one definite orientation.

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text: PGE2 and PGE1 are 20 carbon metabolites of arachidonic acid and dihomo-γ-linolenic acid, respectively, with a double bond between carbons 13 and 14, a carbon-carbon bond between carbons 8 and 12 (which establishes their cyclopentanone structure), hydroxyl residues at carbons 11 and 15, and a ketol residue at carbon 9. They differ in that PGE2 has, while PGE1 lacks, a double bound between carbons 5 and 6. Both PGs undergo a dehydration reaction across their 11-hydroxyl-carbon 10 regions to form a new double bond between carbons 10 and 11 to become PGA2 and PGA1, respectively, with a cyclopenenone ring replacing the cyclopentaonon rings or their recursors and a newly established electrophilic site at carbon 11. This electrophilic site is probably less electrophilic that the carbon 9 sites of Δ12-PGJ2 and 15-deoxy-Δ12-PGJ2

text: PGE2 and PGE1 are 20 carbon metabolites of arachidonic acid and

text: dihomo-γ-linolenic acid

text: , respectively, with a double bond between carbons 13 and 14, a carbon-carbon bond between carbons 8 and 12 (which establishes their cyclopentanone structure), hydroxyl residues at carbons 11 and 15, and a ketol residue at carbon 9. They differ in that PGE2 has, while PGE1 lacks, a double bound between carbons 5 and 6. Both PGs undergo a dehydration reaction across their 11-hydroxyl-carbon 10 regions to form a new double bond between carbons 10 and 11 to become PGA2 and PGA1, respectively, with a cyclopenenone ring replacing the cyclopentaonon rings or their recursors and a newly established electrophilic site at carbon 11. This electrophilic site is probably less electrophilic that the carbon 9 sites of Δ12-PGJ2 and 15-deoxy-Δ12-PGJ2

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracies.

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text: A common dynamic covalent building motif is bond formation between a carbon center and a heteroatom such as nitrogen or oxygen. Because the bond formed between carbon and a heteroatom is less stable than a carbon-carbon bond, they offer more reversibility and reach thermodynamic equilibrium faster than carbon bond forming dynamic covalent reactions.

text: A common dynamic covalent building motif is bond formation between a carbon center and a heteroatom such as nitrogen or oxygen. Because the bond formed between carbon and a heteroatom is less stable than a carbon-carbon bond, they offer more reversibility and reach thermodynamic equilibrium faster than carbon bond forming dynamic covalent reactions.

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text: Differences in crystal structure and chemistry greatly influence other physical properties of the mineral. The carbon allotropes diamond and graphite have vastly different properties; diamond is the hardest natural substance, has an adamantine lustre, and belongs to the isometric crystal family, whereas as graphite is very soft, has a greasy lustre, and crystallises in the hexagonal family. This difference is accounted by differences in bonding. In diamond, the carbons are in sp hybrid orbitals, which means they form a framework where each carbon is covalently bonded to four neighbours in a tetrahedral fashion; on the other hand, graphite is composed of sheets of carbons in sp hybrid orbitals, where each carbon is bonded covalently to only three others. These sheets are held together by much weaker van der Waals forces, and this discrepancy translates to big macroscopic differences.

text: Differences in crystal structure and chemistry greatly influence other physical properties of the mineral. The carbon allotropes

text: diamond

text: and

text: graphite

text: have vastly different properties; diamond is the hardest natural substance, has an adamantine lustre, and belongs to the isometric crystal family, whereas as graphite is very soft, has a greasy lustre, and crystallises in the hexagonal family. This difference is accounted by differences in bonding. In diamond, the carbons are in sp hybrid orbitals, which means they form a framework where each carbon is covalently bonded to four neighbours in a tetrahedral fashion; on the other hand, graphite is composed of sheets of carbons in sp hybrid orbitals, where each carbon is bonded covalently to only three others. These sheets are held together by much weaker

text: van der Waals force

text: s, and this discrepancy translates to big macroscopic differences.

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answers: Hydrocarbon

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answers: graphite

answers: NDQ_016400

answers: three

answers: NDQ_016401

answers: Allotropes

text: Homocapsaicin is a capsaicinoid and analog and congener of capsaicin in  chili peppers (Capsicum). Like capsaicin it is an irritant. Homocapsaicin accounts for about 1% of the total capsaicinoids mixture and has about half the pungency of capsaicin. Pure homocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. On the Scoville scale it has 8 600 000 SHU (Scoville heat units). Homocapsaicin isolated from chili pepper has been found in two isomeric forms, both with a carbon-carbon double bond at the 6 position (numbered from the amide carbon) on the 10-carbon acyl chain. One isomer has an additional carbon, a methyl group, at the 8 position and the other has a methyl group at the 9 position. Homocapsaicin (6-ene-8-methyl) is the more abundant isomer. Homocapsaicin with the double bond at the 7 position has never been found in nature, though its structure is widely reported on the Internet and, unfortunately, even in the scientific literature. Details of the misidentification have been published.(Note:  the structure to the right is incorrect and has not yet been edited.)

text: Homocapsaicin is a capsaicinoid and analog and

text: congener

text: of

text: capsaicin

text: in

text: chili pepper

text: s (

text: Capsicum

text: ). Like capsaicin it is an

text: irritant

text: . Homocapsaicin accounts for about 1% of the total capsaicinoids mixture and has about half the pungency of capsaicin. Pure homocapsaicin is a

text: lipophilic

text: colorless odorless crystalline to waxy compound. On the

text: Scoville scale

text: it has 8 600 000 SHU (Scoville heat units). Homocapsaicin isolated from chili pepper has been found in two isomeric forms, both with a carbon-carbon double bond at the 6 position (numbered from the amide carbon) on the 10-carbon acyl chain. One isomer has an additional carbon, a methyl group, at the 8 position and the other has a methyl group at the 9 position. Homocapsaicin (6-ene-8-methyl) is the more abundant isomer. Homocapsaicin with the double bond at the 7 position has never been found in nature, though its structure is widely reported on the Internet and, unfortunately, even in the scientific literature. Details of the misidentification have been published.(Note:  the structure to the right is incorrect and has not yet been edited.)

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text: It is important to note that A-values do not predict the physical size of a molecule, only the steric effect.  For example, the tert-butyl group (A-value=4.9) has a larger A-value than the trimethylsilyl group (A-value=2.5), yet the tert-butyl group actually occupies less space.  This difference can be attributed to the longer length of the carbon-silicon bond as compared to the carbon-carbon bond of the tert-butyl group.  The longer bond allows for less interactions with neighboring substituents, which effectively makes the trimethylsilyl group less sterically hindering, thus, lowering its A-value.  This can also be seen when comparing the halogens.  Bromine, iodine, and chlorine all have similar A-values even though their atomic radii differ. A-values then, predict the apparent size of a substituent, and the relative apparent sizes determine the differences in steric effects between compounds.   Thus, A-values are useful tools in determining compound reactivity in chemical reactions.

text: It is important to note that A-values do not predict the physical size of a molecule, only the steric effect.  For example, the tert-butyl group (A-value=4.9) has a larger A-value than the

text: trimethylsilyl

text: group (A-value=2.5), yet the tert-butyl group actually occupies less space.  This difference can be attributed to the longer length of the

text: carbon-silicon bond

text: as compared to the

text: carbon-carbon bond

text: of the tert-butyl group.  The longer bond allows for less interactions with neighboring substituents, which effectively makes the trimethylsilyl group less sterically hindering, thus, lowering its A-value.  This can also be seen when comparing the

text: halogen

text: s.  Bromine, iodine, and chlorine all have similar A-values even though their atomic radii differ. A-values then, predict the apparent size of a substituent, and the relative apparent sizes determine the differences in steric effects between compounds.   Thus, A-values are useful tools in determining compound reactivity in chemical reactions.

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text: Carbon monoxide bonds to transition metals using "synergistic π back-bonding." The bonding has three components, giving rise to a partial triple bond. A sigma bond arises from overlap of the nonbonding (or weakly anti-bonding) sp-hybridized electron pair on carbon with a blend of d-, s-, and p-orbitals on the metal. A pair of π bonds arises from overlap of filled d-orbitals on the metal with a pair of π-antibonding orbitals projecting from the carbon atom of the CO. The latter kind of binding requires that the metal have d-electrons, and that the metal is in a relatively low oxidation state (<+2) which makes the back donation process favorable. As electrons from the metal fill the π-antibonding orbital of CO, they weaken the carbon-oxygen bond compared with free carbon monoxide, while the metal-carbon bond is strengthened. Because of the multiple bond character of the M-CO linkage, the distance between the metal and carbon atom is relatively short, often < 1.8 Â, about 0.2 Â shorter than a metal-alkyl bond. Several canonical forms can be drawn to describe the approximate metal carbonyl bonding modes.

text: Carbon monoxide bonds to transition metals using "synergistic

text: π back-bonding

text: ." The bonding has three components, giving rise to a partial triple bond. A

text: sigma bond

text: arises from overlap of the nonbonding (or weakly anti-bonding) sp-hybridized electron pair on carbon with a blend of d-, s-, and p-orbitals on the metal. A pair of π bonds arises from overlap of filled d-orbitals on the metal with a pair of π-antibonding orbitals projecting from the carbon atom of the CO. The latter kind of binding requires that the metal have d-electrons, and that the metal is in a relatively low oxidation state (<+2) which makes the back donation process favorable. As electrons from the metal fill the π-antibonding orbital of CO, they weaken the

text: carbon-oxygen bond

text: compared with free carbon monoxide, while the metal-carbon bond is strengthened. Because of the multiple bond character of the M-CO linkage, the distance between the metal and carbon atom is relatively short, often < 1.8 Â, about 0.2 Â shorter than a metal-alkyl bond. Several

text: canonical forms

text: can be drawn to describe the approximate metal carbonyl bonding modes.

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answers: Carbon monoxide

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answers: carbonyl

answers: NDQ_016399

answers: Carbon monoxide

answers: NDQ_016400

answers: d-

answers: NDQ_016401

answers: Carbon monoxide

text: The mechanism of the Jacobsen–Katsuki epoxidation is not fully understood, but most likely a manganese(V)-species (similar to the ferryl intermediate of Cytochrome P450) is the reactive intermediate which is formed upon the oxidation of the Mn(III)-salen complex. There are three major pathways. The concerted pathway, the metalla oxetane pathway and the radical pathway. The most accepted mechanism is the concerted pathway mechanism. After the formation of the Mn(V) complex, the catalyst is activated and therefore can form epoxides with alkenes. The alkene comes in from the "top-on" approach (above the plane of the catayst) and the oxygen atom now is bonded to the two carbon atoms (previously C=C bond) and is still bonded to the manganese metal. Then, the Mn–O bond breaks and the epoxide is formed. The Mn(III)-salen complex is regenerated, which can then be oxidized again to form the Mn(V) complex.

text: The mechanism of the Jacobsen–Katsuki epoxidation is not fully understood, but most likely a manganese(V)-species (similar to the

text: ferryl

text: intermediate of

text: Cytochrome P450

text: ) is the reactive intermediate which is formed upon the oxidation of the Mn(III)-

text: salen complex

text: . There are three major pathways. The concerted pathway, the metalla oxetane pathway and the radical pathway. The most accepted mechanism is the concerted pathway mechanism. After the formation of the Mn(V) complex, the catalyst is activated and therefore can form epoxides with alkenes. The alkene comes in from the "top-on" approach (above the plane of the catayst) and the oxygen atom now is bonded to the two carbon atoms (previously C=C bond) and is still bonded to the manganese metal. Then, the Mn–O bond breaks and the epoxide is formed. The Mn(III)-salen complex is regenerated, which can then be oxidized again to form the Mn(V) complex.

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answers: alkenes

answers: NDQ_016396

answers: C=C bond

answers: NDQ_016398

answers: alkenes

answers: NDQ_016399

answers: C=C bond

answers: NDQ_016400

answers: three

answers: NDQ_016401

answers: alkenes

text: The Newman projection and the sawhorse projection are used to depict specific conformers or to distinguish vicinal stereochemistry. In both cases, two specific carbon atoms and their connecting bond are the center of attention. The only difference is a slightly different perspective: the Newman projection looking straight down the bond of interest, the sawhorse projection looking at the same bond but from a somewhat oblique vantage point. In the Newman projection, a circle is used to represent a plane perpendicular to the bond, distinguishing the substituents on the front carbon from the substituents on the back carbon. In the sawhorse projection, the front carbon is usually on the left and is always slightly lower:

text: The

text: Newman projection

text: and the

text: sawhorse

text: projection are used to depict specific

text: conformers

text: or to distinguish

text: vicinal

text: stereochemistry. In both cases, two specific carbon atoms and their connecting bond are the center of attention. The only difference is a slightly different perspective: the Newman projection looking straight down the bond of interest, the sawhorse projection looking at the same bond but from a somewhat

text: oblique

text: vantage point. In the Newman projection, a circle is used to represent a plane perpendicular to the bond, distinguishing the substituents on the front carbon from the substituents on the back carbon. In the sawhorse projection, the front carbon is usually on the left and is always slightly lower:

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answers: The Newman projection looking straight down the bond of interest

answers: NDQ_016396

answers: their connecting bond

answers: NDQ_016398

answers: Hydrocarbon

answers: NDQ_016399

answers: The Newman projection looking straight down the bond of interest

answers: NDQ_016400

answers: back carbon

answers: NDQ_016401

answers: Carbon can form more compounds than any other element.

text: The reaction mechanism for an alkene bromination can be described as follows. In the first step of the reaction, a bromine molecule approaches the electron-rich  alkene carbon–carbon double bond. The bromine atom closer to the bond takes on a partial positive charge as its electrons are repelled by the electrons of the double bond.

text: The

text: reaction mechanism

text: for an alkene bromination can be described as follows. In the first step of the reaction, a bromine molecule approaches the electron-rich

text: alkene

text: carbon–carbon double bond. The bromine atom closer to the bond takes on a partial positive charge as its

text: electron

text: s are repelled by the electrons of the double bond.

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answers: carbon

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answers: alkene

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answers: electron-rich

answers: NDQ_016401

answers: carbon

text: The Hiyama coupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon bonds (C-C bonds). This reaction was discovered in 1988 by Tamejiro Hiyama and Yasuo Hatanaka as a method to form carbon-carbon bonds synthetically with chemo- and regioselectivity. This reaction has been applied to the synthesis of various natural products.

text: The Hiyama coupling is a

text: palladium

text: -catalyzed

text: cross-coupling reaction

text: of

text: organosilanes

text: with

text: organic halides

text: used in

text: organic chemistry

text: to form

text: carbon–carbon bond

text: s (C-C bonds). This reaction was discovered in 1988 by Tamejiro Hiyama and Yasuo Hatanaka as a method to form carbon-carbon bonds synthetically with

text: chemo

text: - and

text: regioselectivity

text: . This reaction has been applied to the synthesis of various

text: natural product

text: s.

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text: In molecules such as methane, , the eight valence electrons are found in four MOs that are spread out over all five atoms. However, it is possible to transform the MOs into four localized sp orbitals. Linus Pauling, in 1931, hybridized the carbon 2s and 2p orbitals so that they pointed directly at the hydrogen 1s basis functions and featured maximal overlap. However, the delocalized MO description is more appropriate for predicting ionization energies and the positions of spectral absorption bands. When methane is ionized, a single electron is taken from the valence MOs, which can come from the s bonding or the triply degenerate p bonding levels, yielding two ionization energies. In comparison, the explanation in VB theory is more complicated. When one electron is removed from an sp orbital, resonance is invoked between four valence bond structures, each of which has a single one-electron bond and three two-electron bonds. Triply degenerate T and A ionized states (CH) are produced from different linear combinations of these four structures. The difference in energy between the ionized and ground state gives the two ionization energies.

text: In molecules such as

text: methane

text: , , the eight valence electrons are found in four MOs that are spread out over all five atoms. However, it is possible to transform the MOs into four localized sp orbitals. Linus Pauling, in 1931, hybridized the carbon 2s and 2p orbitals so that they pointed directly at the

text: hydrogen

text: 1s basis functions and featured maximal overlap. However, the delocalized MO description is more appropriate for predicting

text: ionization energies

text: and the positions of spectral

text: absorption band

text: s. When methane is ionized, a single electron is taken from the valence MOs, which can come from the s bonding or the triply degenerate p bonding levels, yielding two ionization energies. In comparison, the explanation in VB theory is more complicated. When one electron is removed from an sp orbital,

text: resonance

text: is invoked between four valence bond structures, each of which has a single one-electron bond and three two-electron bonds. Triply degenerate T and A ionized states (CH) are produced from different linear combinations of these four structures. The difference in energy between the ionized and ground state gives the two ionization energies.

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text: The carbon-hydrogen bond (C–H bond) is a bond between carbon and hydrogen atoms that can be found in many organic compounds. This bond is a covalent bond meaning that carbon shares its outer valence electrons with up to four hydrogens.  This completes both of their outer shells making them stable. Carbon–hydrogen bonds have a bond length of about 1.09 Å (1.09 × 10 m) and a bond energy of about 413 kJ/mol (see table below).  Using Pauling's scale—C (2.55) and H (2.2)—the electronegativity difference between these two atoms is 0.35. Because of this small difference in electronegativities, the C−H bond is generally regarded as being non-polar. In structural formulas of molecules, the hydrogen atoms are often omitted. Compound classes consisting solely of C–H bonds and C–C bonds are alkanes, alkenes, alkynes, and aromatic hydrocarbons. Collectively they are known as hydrocarbons.

text: The carbon-hydrogen bond (C–H bond) is a

text: bond

text: between

text: carbon

text: and

text: hydrogen

text: atoms that can be found in many

text: organic compound

text: s. This bond is a covalent bond meaning that carbon shares its outer valence electrons with up to four hydrogens.  This completes both of their outer shells making them stable. Carbon–hydrogen bonds have a

text: bond length

text: of about 1.09

text: Å

text: (1.09 × 10 m) and a

text: bond energy

text: of about 413

text: kJ

text: mol

text: (see table below).  Using

text: Pauling's scale

text: —C (2.55) and H (2.2)—the electronegativity difference between these two atoms is 0.35. Because of this small difference in electronegativities, the C−H bond is generally regarded as being non-polar. In

text: structural formula

text: s of molecules, the hydrogen atoms are often omitted. Compound classes consisting solely of C–H bonds and

text: C–C

text: bonds are

text: alkane

text: s,

text: alkene

text: s,

text: alkyne

text: s, and

text: aromatic hydrocarbon

text: s. Collectively they are known as

text: hydrocarbons

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text: 1-dimensional silicyne is analogous to the carbon allotrope carbyne, being a long chain of silicons, instead of carbons. It is amorphous silicon with sp hybridization of the valence electrons. Silicyne is a single linear molecule composed of just silicon atoms. One of the manners they are bonded to each other in a succession of double-bonded silicons, analogous to the situation of carbon found in cumulene. The other manner they may be bonded to each other is a succession of alternating single and triple-bonded silicons, analogous to the situation of carbon found in polyyne.

text: 1-dimensional silicyne is analogous to the

text: carbon allotrope

text: carbyne

text: , being a long chain of silicons, instead of carbons. It is amorphous silicon with

text: sp hybridization

text: of the

text: valence electron

text: s. Silicyne is a single linear molecule composed of just silicon

text: atom

text: s. One of the manners they are

text: bond

text: ed to each other in a succession of

text: double-bond

text: ed silicons, analogous to the situation of

text: carbon

text: found in

text: cumulene

text: . The other manner they may be bonded to each other is a succession of alternating

text: single

text: and

text: triple

text: bond

text: ed silicons, analogous to the situation of carbon found in

text: polyyne

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answers: carbon allotrope carbyne

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answers: triple-bonded

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answers: polyyne

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answers: valence

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answers: It is a long chain of silicons

text: Shorter than average C–C bond distances are also possible: alkenes and alkynes have bond lengths of respectively 133 and 120 pm due to increased s-character of the sigma bond. In benzene all bonds have the same length: 139 pm. Carbon–carbon single bonds increased s-character is also notable in the central bond of diacetylene (137 pm) and that of a certain tetrahedrane dimer (144 pm).

text: Shorter than average C–C bond distances are also possible:

text: alkene

text: s and

text: alkyne

text: s have bond lengths of respectively 133 and 120 pm due to increased

text: s-character

text: of the

text: sigma bond

text: . In

text: benzene

text: all bonds have the same length: 139 pm. Carbon–carbon single bonds increased s-character is also notable in the central bond of

text: diacetylene

text: (137 pm) and that of a certain

text: tetrahedrane dimer

text: (144 pm).

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answers: Carbon–carbon single bonds

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answers: carbon–carbon

text: Carbon is a key component of all known life on Earth. Complex molecules are made up of carbon bonded with other elements, especially oxygen, hydrogen and nitrogen, and carbon can bond with all of these because of its four valence electrons. Carbon is abundant on Earth. It is also lightweight and relatively small in size, making it easier for enzymes to manipulate carbonmolecules. It is often assumed in astrobiology that if life exists somewhere else in the universe, it will also be carbon-based. Critics refer to this assumption as carbon chauvinism.

text: Carbon is a key component of all known

text: life

text: on

text: Earth

text: . Complex

text: molecule

text: s are made up of carbon

text: bonded

text: with other

text: elements

text: , especially

text: oxygen

text: hydrogen

text: and

text: nitrogen

text: , and carbon can bond with all of these because of its four

text: valence electrons

text: . Carbon is abundant on Earth. It is also lightweight and relatively small in size, making it easier for enzymes to manipulate carbonmolecules. It is often assumed in

text: astrobiology

text: that if life exists somewhere else in the

text: universe

text: , it will also be carbon-based. Critics refer to this assumption as

text: carbon chauvinism

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answers: Carbon is abundant on Earth

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answers: four valence electrons

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answers: Hydrogen

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answers: no

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answers: Carbon is abundant on Earth

text: The association of the cation bonding electrons with the anion in the ionic model is purely formal.  There is no change in physical locations of any electrons, and there is no change in the bond valence.  The terms "anion" and "cation" in the bond valence model are defined in terms of the bond topology, not the chemical properties of the atoms.  This extends the scope of the ionic model well beyond compounds in which the bonding would normally be considered as "ionic".  For example, methane, CH, obeys the conditions for the ionic model with carbon as the cation and hydrogen as the anion (or vice versa, since carbon and hydrogen have the same electronegativity).

text: The association of the cation bonding electrons with the anion in the ionic model is purely formal.  There is no change in physical locations of any electrons, and there is no change in the bond valence.  The terms "anion" and "cation" in the bond valence model are defined in terms of the bond topology, not the chemical properties of the atoms.  This extends the scope of the ionic model well beyond compounds in which the bonding would normally be considered as "ionic".  For example, methane, CH, obeys the conditions for the ionic model with carbon as the cation and hydrogen as the anion (or vice versa, since carbon and hydrogen have the same electronegativity).

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answers: This extends the scope of the ionic model

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answers: It can form more compounds than any other element

text: The reaction of an electrophile with 1,3,2,4-dithiadiphosphetane 2,4-disulfides is less common, but the reaction of an alkyl halide with a 1,3,2,4-dithiadiphosphetane 2,4-disulfide forms a new compound with a sulfur-carbon bond and a phosphorus-halide bond. Such a compound could act as an acetylcholinesterase inhibitor in insects, but in order to make a better insecticide it would be best to convert the halide to another leaving group which would form a less water sensitive product. For instance the reaction of para-nitrophenolate would form a compound similar to parathion.

text: The reaction of an

text: electrophile

text: with 1,3,2,4-dithiadiphosphetane 2,4-disulfides is less common, but the reaction of an

text: alkyl

text: halide

text: with a 1,3,2,4-dithiadiphosphetane 2,4-disulfide forms a new compound with a

text: sulfur

text: carbon

text: bond

text: and a

text: phosphorus

text: halide

text: bond. Such a compound could act as an

text: acetylcholinesterase

text: inhibitor

text: in insects, but in order to make a better

text: insecticide

text: it would be best to convert the halide to another

text: leaving group

text: which would form a less water sensitive product. For instance the reaction of para-nitrophenolate would form a compound similar to

text: parathion

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answers: It would be best to convert the halide to another leaving group

text: Advocates of the non-classical nature of the stable 2-norbornyl cation typically depict the species using either resonance structures or a single structure with partial bonds (see Figure 2). This hypovalent interaction can be imagined as the net effect of i) a partial sigma bond between carbons 1 and 6, ii) a partial sigma bond between carbons 2 and 6, and iii) a partial pi bond between carbons 1 and 2. Each partial bond is represented as a full bond in one of the three resonance structures or as a dashed partial bond if the cation is depicted through a single structure.

text: Advocates of the non-classical nature of the stable 2-norbornyl cation typically depict the species using either

text: resonance structures

text: or a single structure with partial bonds (see Figure 2). This hypovalent interaction can be imagined as the net effect of i) a partial

text: sigma bond

text: between carbons 1 and 6, ii) a partial sigma bond between carbons 2 and 6, and iii) a partial

text: pi bond

text: between carbons 1 and 2. Each partial bond is represented as a full bond in one of the three resonance structures or as a dashed partial bond if the cation is depicted through a single structure.

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text: Alkeneynes are acyclic branched or unbranched hydrocarbons having one carbon–carbon double bond and one carbon–carbon triple bond.

text: Alkeneynes are acyclic branched or unbranched

text: hydrocarbon

text: s having one carbon–carbon double bond and one carbon–carbon triple bond.

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text: He was born in Georgetown, Guyana in 1957. After moving to the United States after high school, Periana studied and received a B.S. in chemistry at the University of Michigan in 1979. He then worked in industry at the Dow Chemical Company in Midland, Michigan. In 1981, he returned to graduate school at the University of California Berkeley where he received his Ph.D. in 1985 under Robert G. Bergman. His work with Bergman focused on the development of novel rhodium complexes that undergo C-H and C-C bond activation of alkanes. His dissertation was entitled, "Mechanism of Oxidative Addition of Cyclopentadienyl-Rhodium Complexes to Carbon-Hydrogen and Carbon-Carbon Bonds."

text: He was born in

text: Georgetown, Guyana

text: in 1957. After moving to the United States after high school, Periana studied and received a B.S. in

text: chemistry

text: at the

text: University of Michigan

text: in 1979. He then worked in industry at the

text: Dow Chemical

text: Company in

text: Midland, Michigan

text: . In 1981, he returned to graduate school at the

text: University of California Berkeley

text: where he received his Ph.D. in 1985 under

text: Robert G. Bergman

text: . His work with Bergman focused on the development of novel

text: rhodium

text: complexes that undergo C-H and C-C bond activation of

text: alkanes

text: . His

text: dissertation

text: was entitled, "Mechanism of Oxidative Addition of Cyclopentadienyl-Rhodium Complexes to Carbon-Hydrogen and Carbon-Carbon Bonds."

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answers: Carbon

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answers: Carbon

text: The discoverers of the Buckminsterfullerene (C) allotrope of carbon named it after Richard Buckminster Fuller, a noted architectural modeler who popularized the geodesic dome. Since buckminsterfullerenes have a similar shape to those of such domes, they thought the name appropriate.<br>As the discovery of the fullerene family came after buckminsterfullerene, the shortened name 'fullerene' is used to refer to the family of fullerenes. The suffix "-ene" indicates that each C atom is covalently bonded to three others (instead of the maximum of four), a situation that classically would correspond to the existence of bonds involving two pairs of electrons ("double bonds").

text: The discoverers of the

text: Buckminsterfullerene

text: (C)

text: allotrope

text: of

text: carbon

text: named it after

text: Richard Buckminster Fuller

text: , a noted architectural modeler who popularized the

text: geodesic dome

text: . Since buckminsterfullerenes have a similar shape to those of such domes, they thought the name appropriate.<br>As the discovery of the fullerene family came after buckminsterfullerene, the shortened name 'fullerene' is used to refer to the family of fullerenes. The suffix "-ene" indicates that each C atom is covalently bonded to three others (instead of the maximum of four), a situation that classically would correspond to the existence of bonds involving two pairs of electrons ("

text: double bond

text: s").

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answers: It can form more compounds than any other element.

text: The carbopalladation step is regioselective when unsymmetrical alkynes are used. Although it was previously believed that the alkyne is inserted with the less sterically-hindering R-group adjacent to the arylpalladium, Larock et al. observed that the larger more sterically-hindering R-group is inserted next to the arylpalladium. They suggest that the driving force of the alkyne insertion may be the steric hindrance present in the developing carbon-carbon bond and the orientation of the alkyne prior to syn-insertion of the alkyne into the aryl palladium bond. Alkyne insertion occurs so that the large substituent on the alkyne avoids steric strain from the short developing carbon-carbon bond by interacting with the longer carbon-palladium bond.

text: The carbopalladation step is regioselective when unsymmetrical alkynes are used. Although it was previously believed that the alkyne is inserted with the less sterically-hindering R-group adjacent to the arylpalladium, Larock et al. observed that the larger more sterically-hindering R-group is inserted next to the arylpalladium. They suggest that the driving force of the alkyne insertion may be the steric hindrance present in the developing carbon-carbon bond and the orientation of the alkyne prior to syn-insertion of the alkyne into the aryl palladium bond. Alkyne insertion occurs so that the large substituent on the alkyne avoids steric strain from the short developing carbon-carbon bond by interacting with the longer carbon-palladium bond.

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text: An example is the MO description of benzene, , which is an aromatic hexagonal ring of six carbon atoms and three double bonds. In this molecule, 24 of the 30 total valence bonding electrons—24 coming from carbon atoms and 6 coming from hydrogen atoms—are located in 12 σ (sigma) bonding orbitals, which are located mostly between pairs of atoms (C-C or C-H), similarly to the electrons in the valence bond description. However, in benzene the remaining six bonding electrons are located in three π (pi) molecular bonding orbitals that are delocalized around the ring. Two of these electrons are in an MO that has equal orbital contributions from all six atoms. The other four electrons are in orbitals with vertical nodes at right angles to each other. As in the VB theory, all of these six delocalized π electrons reside in a larger space that exists above and below the ring plane. All carbon-carbon bonds in benzene are chemically equivalent. In MO theory this is a direct consequence of the fact that the three molecular π orbitals combine and evenly spread the extra six electrons over six carbon atoms.

text: An example is the MO description of

text: benzene

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answers: carbon-carbon bonds

text: Carbon–carbon bond-forming reactions are organic reactions in which a new carbon–carbon bond is formed. They are important in the production of many man-made chemicals such as pharmaceuticals and plastics.

text: Carbon–carbon bond-forming reactions are

text: organic reaction

text: s in which a new carbon–carbon bond is formed. They are important in the production of many man-made chemicals such as

text: pharmaceutical

text: s and

text: plastic

text: s.

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answers: carbon–carbon bond

text: A carbon–nitrogen bond is a covalent bond between carbon and nitrogen and is one of the most abundant bonds in organic chemistry and biochemistry.

text: A carbon–nitrogen bond is a

text: covalent bond

text: between

text: carbon

text: and

text: nitrogen

text: and is one of the most abundant bonds in

text: organic chemistry

text: and

text: biochemistry

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answers: carbon–nitrogen bond

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answers: covalent

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answers: carbon–nitrogen bond

text: Unsaturated fatty acids have one or more double bonds between carbon atoms. (Pairs of carbon atoms connected by double bonds can be saturated by adding hydrogen atoms to them, converting the double bonds to single bonds. Therefore, the double bonds are called unsaturated.)

text: Unsaturated fatty acids have one or more

text: double bond

text: s between carbon atoms. (Pairs of carbon atoms connected by double bonds can be saturated by adding hydrogen atoms to them, converting the double bonds to single bonds. Therefore, the double bonds are called unsaturated.)

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text: Any hydrogen atoms bonded to non-carbon atoms are drawn explicitly. In ethanol, CHOH, for instance, the hydrogen atom bonded to oxygen is denoted by the symbol H, whereas the hydrogen atoms which are bonded to carbon atoms are not shown directly. Lines representing heteroatom-hydrogen bonds are usually omitted for clarity and compactness, so a functional group like the hydroxyl group is most often written −OH instead of −O−H. These bonds are sometimes drawn out in full in order to accentuate their presence when they participate in reaction mechanisms.

text: Any hydrogen atoms bonded to non-carbon atoms are drawn explicitly. In

text: ethanol

text: , CHOH, for instance, the hydrogen atom bonded to oxygen is denoted by the symbol H, whereas the hydrogen atoms which are bonded to carbon atoms are not shown directly. Lines representing heteroatom-hydrogen bonds are usually omitted for clarity and compactness, so a functional group like the

text: hydroxyl

text: group is most often written −OH instead of −O−H. These bonds are sometimes drawn out in full in order to accentuate their presence when they participate in

text: reaction mechanism

text: s.

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text: forming a total of three sp orbitals with one remaining p orbital. In ethylene (ethene) the two carbon atoms form a σ bond by overlapping two sp orbitals and each carbon atom forms two covalent bonds with hydrogen by s–sp overlap all with 120° angles. The π bond between the carbon atoms perpendicular to the molecular plane is formed by 2p–2p overlap. The hydrogen–carbon bonds are all of equal strength and length, in agreement with experimental data.

text: forming a total of three sp orbitals with one remaining p orbital. In ethylene (

text: ethene

text: ) the two carbon atoms form a σ bond by overlapping two sp orbitals and each carbon atom forms two covalent bonds with hydrogen by s–sp overlap all with 120° angles. The π bond between the carbon atoms perpendicular to the molecular plane is formed by 2p–2p overlap. The hydrogen–carbon bonds are all of equal strength and length, in agreement with experimental data.

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answers: ethylene (ethene)

text: Most theoretical explorations of advanced machines of this kind have focused on using carbon, because of the many strong bonds it can form, the many types of chemistry these bonds permit, and utility of these bonds in medical and mechanical applications. Carbon forms diamond, for example, which if cheaply available, would be an excellent material for many machines.

text: Most theoretical explorations of advanced machines of this kind have focused on using

text: carbon

text: , because of the many strong bonds it can form, the many types of chemistry these bonds permit, and utility of these bonds in medical and mechanical applications. Carbon forms diamond, for example, which if cheaply available, would be an excellent material for many machines.

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answers: NDQ_016401

answers: many strong bonds

text: In organic chemistry, carbenes are molecules which have carbon atoms with only have six valence electrons and therefore disobey the octet rule. Carbenes generally split into singlet carbenes and triplet carbenes, named for their spin multiplicities. Both have two non-bonding electrons; in singlet carbenes these exist as a lone pair and have opposite spins so that there is no net spin, while in triplet carbenes these electrons have parallel spins.

text: In

text: organic chemistry

text: carbene

text: s are molecules which have carbon atoms with only have six valence electrons and therefore disobey the

text: octet rule

text: . Carbenes generally split into

text: singlet

text: carbenes and

text: triplet

text: carbenes, named for their spin multiplicities. Both have two non-bonding electrons; in singlet carbenes these exist as a

text: lone pair

text: and have opposite spins so that there is no net spin, while in triplet carbenes these electrons have parallel spins.

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answers: organic chemistry

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answers: six

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answers: molecules which have carbon atoms with only have six valence electrons

answers: NDQ_016399

answers: triplet carbenes

answers: NDQ_016400

answers: parallel

answers: NDQ_016401

answers: Carbenes

text: Benzene, CH, is the simplest aromatic hydrocarbon, and it was the first one named as such. The nature of its bonding was first recognized by August Kekulé in the 19th century. Each carbon atom in the hexagonal cycle has four electrons to share. One goes to the hydrogen atom, and one each to the two neighbouring carbons. This leaves one electron to share with one of the same two neighbouring carbon atoms, thus creating a double bond with one carbon and leaving a single bond with the other, which is why the benzene molecule is drawn with alternating single and double bonds around the hexagon.

text: Benzene

text: , CH, is the simplest aromatic hydrocarbon, and it was the first one named as such. The nature of its bonding was first recognized by

text: August Kekulé

text: in the 19th century. Each carbon atom in the hexagonal cycle has four electrons to share. One goes to the hydrogen atom, and one each to the two neighbouring carbons. This leaves one electron to share with one of the same two neighbouring carbon atoms, thus creating a double bond with one carbon and leaving a single bond with the other, which is why the benzene molecule is drawn with alternating single and double bonds around the hexagon.

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answers: hydrocarbon

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answers: double bond

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answers: Benzene

answers: NDQ_016399

answers: Benzene

answers: NDQ_016400

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answers: NDQ_016401

answers: Hydrocarbons

text: 4. After the final substituent, name the carbon chain by the name of the number of carbons (1 carbon = meth-, 2 carbons = eth-, 3 carbons = prop-, 4 carbons = but-, 5 carbons = pent-, 6 carbons = hex-, 7 carbons = hept-, 8 carbons = oct-, 9 carbons = non-). Then add "an" for a saturated carbon chain and "en" for a carbon chain with a double bond. Finally, end with "-oic acid".

text: 4. After the final substituent, name the carbon chain by the name of the number of carbons (1 carbon = meth-, 2 carbons = eth-, 3 carbons = prop-, 4 carbons = but-, 5 carbons = pent-, 6 carbons = hex-, 7 carbons = hept-, 8 carbons = oct-, 9 carbons = non-). Then add "an" for a saturated carbon chain and "en" for a carbon chain with a double bond. Finally, end with "-oic acid".

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answers: carbon

text: In organic chemistry, a saturated compound is a chemical compound that has a chain of carbon atoms linked together by single bonds. Alkanes are saturated hydrocarbons. An unsaturated compound is a chemical compound that contains carbon-carbon double bonds or triple bonds, such as those found in alkenes or alkynes, respectively. Saturated and unsaturated compounds need not consist only of a carbon atom chain. They can form straight chain, branched chain, or ring arrangements. They can have functional groups, as well. It is in this sense that fatty acids are classified as saturated or unsaturated. The amount of unsaturation of a fatty acid can be determined by finding its iodine number.

text: In

text: organic chemistry

text: , a saturated compound is a

text: chemical compound

text: that has a chain of

text: carbon

text: atom

text: s linked together by

text: single bond

text: s.

text: Alkane

text: s are saturated hydrocarbons. An unsaturated compound is a chemical compound that contains carbon-carbon

text: double bond

text: s or

text: triple bond

text: s, such as those found in

text: alkene

text: s or

text: alkyne

text: s, respectively. Saturated and unsaturated compounds need not consist only of a carbon atom chain. They can form straight chain, branched chain, or ring arrangements. They can have functional groups, as well. It is in this sense that

text: fatty acid

text: s are classified as

text: saturated

text: or

text: unsaturated

text: . The amount of unsaturation of a fatty acid can be determined by finding its

text: iodine number

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answers: Alkanes are saturated hydrocarbons

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text: In the structure shown at the top of the page, R represents a side-chain specific to each amino acid. The carbon atom next to the carboxyl group (which is therefore numbered 2 in the carbon chain starting from that functional group) is called the α–carbon.  Amino acids containing an amino group bonded directly to the alpha carbon are referred to as alpha amino acids.  These include amino acids such as proline which contain secondary amines, which used to be often referred to as "imino acids".

text: In the structure shown at the top of the page, R represents a

text: side-chain

text: specific to each amino acid. The

text: carbon

text: atom next to the

text: carboxyl group

text: (which is therefore numbered 2 in the

text: carbon chain

text: starting from that functional group) is called the

text: α–carbon

text: .  Amino acids containing an

text: amino group

text: bonded directly to the alpha carbon are referred to as alpha amino acids.  These include amino acids such as

text: proline

text: which contain

text: secondary amine

text: s, which used to be often referred to as "imino acids".

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answers: Amino acids

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answers: Amino acids

text: For instance, palladium(II) acetate is reduced by triphenylphosphine to bis(triphenylphosphine)palladium(0) (1) and triphenylphosphine is oxidized to triphenylphosphine oxide. Step A is an oxidative addition in which palladium inserts itself in the aryl to bromide bond. Palladium then forms a π complex with the alkene (3) and in step B the alkene inserts itself in the palladium - carbon bond in a syn addition step. Then follows a torsional strain relieving rotation to the trans isomer (not shown) and step C is a beta-hydride elimination step with the formation of a new palladium - alkene π complex (5). This complex is destroyed in the next step. The palladium(0) compound is regenerated by reductive elimination of the palladium(II) compound by potassium carbonate in the final step, D. In the course of the reaction the carbonate is stoichiometrically consumed and palladium is truly a catalyst and used in catalytic amounts. A similar palladium cycle but with different scenes and actors is observed in the Wacker process.

text: For instance,

text: palladium(II) acetate

text: is reduced by

text: triphenylphosphine

text: to bis(triphenylphosphine)palladium(0) (1) and triphenylphosphine is oxidized to triphenylphosphine oxide. Step A is an

text: oxidative addition

text: in which palladium inserts itself in the aryl to bromide bond. Palladium then forms a

text: π complex

text: with the alkene (3) and in step B the alkene inserts itself in the palladium - carbon bond in a

text: syn addition

text: step. Then follows a

text: torsional strain

text: relieving rotation to the trans isomer (not shown) and step C is a

text: beta-hydride elimination

text: step with the formation of a new palladium - alkene

text: π complex

text: (5). This complex is destroyed in the next step. The palladium(0) compound is regenerated by

text: reductive elimination

text: of the palladium(II) compound by

text: potassium carbonate

text: in the final step, D. In the course of the reaction the carbonate is stoichiometrically consumed and palladium is truly a catalyst and used in catalytic amounts. A similar palladium cycle but with different scenes and actors is observed in the

text: Wacker process

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answers: carbon

text: Pseudouridine (abbreviated by the Greek letter psi- Ψ) is an isomer of the nucleoside uridine in which the uracil is attached via a carbon-carbon instead of a nitrogen-carbon glycosidic bond. It is the most prevalent of the over one hundred different modified nucleosides found in RNA. Ψ is found in all species and in many classes of RNA. Ψ is formed by enzymes called Ψ synthases, which post-transcriptionally isomerize specific uridine residues in RNA in a process termed pseudouridylation.

text: Pseudouridine (abbreviated by the Greek letter psi- Ψ) is an

text: isomer

text: of the

text: nucleoside

text: uridine

text: in which the

text: uracil

text: is attached via a carbon-carbon instead of a nitrogen-carbon

text: glycosidic bond

text: . It is the most prevalent of the over one hundred different modified nucleosides found in

text: RNA

text: . Ψ is found in all species and in many classes of RNA. Ψ is formed by

text: enzymes

text: called Ψ synthases, which post-transcriptionally isomerize specific uridine residues in RNA in a process termed pseudouridylation.

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answers: It is the most prevalent

text: A 90° twist of the C=C bond (which may be determined by the positions of the groups attached to the carbons) requires less energy than the strength of a pi bond, and the bond still holds. This contradicts a common textbook assertion that the p orbitals would be unable sustain such a bond. In truth, the misalignment of the p orbitals is less than expected because pyramidalization takes place (See: pyramidal alkene). trans-Cyclooctene is a stable strained alkene and the orbital misalignment is only 19° with a dihedral angle of 137° (normal 120°) and a degree of pyramidalization of 18°. The trans isomer of cycloheptene is stable only at low temperatures.

text: A 90° twist of the C=C bond (which may be determined by the positions of the groups attached to the carbons) requires less energy than the strength of a

text: pi bond

text: , and the bond still holds. This contradicts a common textbook assertion that the

text: p orbital

text: s would be unable sustain such a bond. In truth, the misalignment of the

text: p orbital

text: s is less than expected because

text: pyramidalization

text: takes place (See:

text: pyramidal alkene

text: ). trans-

text: Cyclooctene

text: is a stable strained alkene and the orbital misalignment is only 19° with a

text: dihedral angle

text: of 137° (normal 120°) and a degree of pyramidalization of 18°. The trans isomer of

text: cycloheptene

text: is stable only at low temperatures.

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text: Polymer degradation by galvanic action was first described in the technical literature in 1990. This was the discovery that "plastics can corrode", i.e.  polymer degradation may occur through galvanic action similar to that of metals under certain conditions and has been referred to as the "Faudree Effect". In the aerospace field, this finding has largely contributed to aircraft safety, mainly those aircraft that use CFRP and has resulted in a wide body of follow-up research and patents. Normally, when two dissimilar metals such as copper (Cu) and iron (Fe) are put into contact and then immersed in salt water, the iron will undergo corrosion, or rust. This is called a galvanic circuit where the copper is the noble metal and the iron is the active metal, i.e., the copper is the positive (+) electrode and the iron is the negative (-) electrode. A battery is formed. It follows that plastics are made stronger by impregnating them with thin carbon fibers only a few micrometers in diameter known as carbon fiber reinforced polymers (CFRP). This is to produce materials that are high strength and resistant to high temperatures. The carbon fibers act as a noble metal similar to gold (Au) or platinum (Pt). When put into contact with a more active metal, for example with aluminum (Al) in salt water the aluminum corrodes. However, in early 1990, it was reported that imide-linked resins in CFRP composites degrade when bare composite is coupled with an active metal in salt water environments. This is because corrosion not only occurs at the aluminum anode, but also at the carbon fiber cathode in the form of a very strong base with a pH of about 13. This strong base reacts with the polymer chain structure degrading the polymer. Polymers affected include bismaleimides (BMI), condensation polyimides, triazines, and blends thereof. Degradation occurs in the form of dissolved resin and loose fibers. The hydroxyl ions generated at the graphite cathode attack the O-C-N bond in the polyimide structure. Standard corrosion protection procedures were found to prevent polymer degradation under most conditions.

text: Polymer degradation by galvanic action was first described in the technical literature in 1990. This was the discovery that "plastics can corrode", i.e.  polymer degradation may occur through galvanic action similar to that of metals under certain conditions and has been referred to as the "Faudree Effect". In the aerospace field, this finding has largely contributed to aircraft safety, mainly those aircraft that use

text: CFRP

text: and has resulted in a wide body of follow-up research and patents. Normally, when two dissimilar metals such as

text: copper

text: (Cu) and

text: iron

text: (Fe) are put into contact and then immersed in salt water, the iron will undergo

text: corrosion

text: , or rust. This is called a

text: galvanic circuit

text: where the copper is the

text: noble metal

text: and the iron is the

text: active metal

text: , i.e., the copper is the positive (+)

text: electrode

text: and the iron is the negative (-)

text: electrode

text: . A

text: battery

text: is formed. It follows that plastics are made stronger by impregnating them with thin

text: carbon fibers

text: only a few micrometers in diameter known as

text: carbon fiber

text: reinforced polymers (

text: CFRP

text: ). This is to produce materials that are high strength and resistant to high temperatures. The carbon fibers act as a noble metal similar to gold (Au) or platinum (Pt). When put into contact with a more active metal, for example with aluminum (Al) in salt water the aluminum corrodes. However, in early 1990, it was reported that imide-linked resins in

text: CFRP

text: composite

text: s degrade when bare composite is coupled with an active metal in salt water environments. This is because corrosion not only occurs at the aluminum

text: anode

text: , but also at the

text: carbon fiber

text: cathode

text: in the form of a very strong base with a

text: pH

text: of about 13. This strong base reacts with the polymer chain structure degrading the polymer. Polymers affected include

text: bismaleimide

text: s (BMI), condensation

text: polyimide

text: s,

text: triazine

text: s, and blends thereof. Degradation occurs in the form of dissolved resin and loose fibers. The

text: hydroxyl ion

text: s generated at the graphite

text: cathode

text: attack the O-C-N bond in the polyimide structure. Standard corrosion protection procedures were found to prevent polymer degradation under most conditions.

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracies.

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text: A molecule of dietary fat typically consists of several fatty acids (containing long chains of carbon and hydrogen atoms), bonded to a glycerol. They are typically found as triglycerides (three fatty acids attached to one glycerol backbone). Fats may be classified as saturated or unsaturated depending on the detailed structure of the fatty acids involved. Saturated fats have all of the carbon atoms in their fatty acid chains bonded to hydrogen atoms, whereas unsaturated fats have some of these carbon atoms double-bonded, so their molecules have relatively fewer hydrogen atoms than a saturated fatty acid of the same length. Unsaturated fats may be further classified as monounsaturated (one double-bond) or polyunsaturated (many double-bonds). Furthermore, depending on the location of the double-bond in the fatty acid chain, unsaturated fatty acids are classified as omega-3 or omega-6 fatty acids. Trans fats are a type of unsaturated fat with trans-isomer bonds; these are rare in nature and in foods from natural sources; they are typically created in an industrial process called (partial) hydrogenation.  There are nine kilocalories in each gram of fat. Fatty acids such as conjugated linoleic acid, catalpic acid, eleostearic acid and punicic acid, in addition to providing energy, represent potent immune modulatory molecules.

text: A molecule of dietary fat typically consists of several

text: fatty acid

text: s (containing long chains of carbon and hydrogen atoms), bonded to a

text: glycerol

text: . They are typically found as

text: triglyceride

text: s (three fatty acids attached to one glycerol backbone). Fats may be classified as

text: saturated

text: or

text: unsaturated

text: depending on the detailed structure of the fatty acids involved. Saturated fats have all of the carbon atoms in their fatty acid chains bonded to hydrogen atoms, whereas unsaturated fats have some of these carbon atoms

text: double-bonded

text: , so their molecules have relatively fewer hydrogen atoms than a saturated fatty acid of the same length. Unsaturated fats may be further classified as monounsaturated (one double-bond) or polyunsaturated (many double-bonds). Furthermore, depending on the location of the double-bond in the fatty acid chain, unsaturated fatty acids are classified as

text: or

text: fatty acids.

text: Trans fat

text: s are a type of unsaturated fat with trans-isomer bonds; these are rare in nature and in foods from natural sources; they are typically created in an industrial process called (partial)

text: hydrogenation

text: .  There are nine kilocalories in each gram of fat. Fatty acids such as

text: conjugated linoleic acid

text: , catalpic acid, eleostearic acid and

text: punicic acid

text: , in addition to providing energy, represent potent immune modulatory molecules.

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text: An important piece of early evidence in support of the homotropylium cation structure that did not rely on the magnetic properties of the molecule involved the acquisition of its UV spectrum. Winstein et al. determined that the absorption maxima for the homotropylium cation exhibited a considerably shorter wavelength than would be precited for the classical cyclooctatrienyl cation or the bicyclo[5.1.0]octadienyl compound with the fully formed internal cyclopropane bond (and a localized electronic structure). Instead, the UV spectrum most resembled that of the aromatic tropylium ion. Further calculations allowed Winstein to determine that the bond order between the two carbon atoms adjacent to the outlying methylene bridge is comparable to that of the π-bond separating the corresponding carbon atoms in the tropylium cation. Although this experiment proved to be highly illuminating, it should be noted that UV spectra are generally considered to be poor indicators of aromaticity or homoaromaticity.

text: An important piece of early evidence in support of the homotropylium cation structure that did not rely on the magnetic properties of the molecule involved the acquisition of its

text: UV spectrum

text: . Winstein et al. determined that the absorption maxima for the homotropylium cation exhibited a considerably shorter

text: wavelength

text: than would be precited for the classical cyclooctatrienyl cation or the bicyclo[5.1.0]octadienyl compound with the fully formed internal cyclopropane bond (and a localized electronic structure). Instead, the UV spectrum most resembled that of the aromatic

text: tropylium ion

text: . Further calculations allowed Winstein to determine that the

text: bond order

text: between the two carbon atoms adjacent to the outlying methylene bridge is comparable to that of the

text: π-bond

text: separating the corresponding carbon atoms in the tropylium cation. Although this experiment proved to be highly illuminating, it should be noted that UV spectra are generally considered to be poor indicators of aromaticity or homoaromaticity.

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text: The thionium ion can be trapped by various intramolecular and intermolecular nucleophiles to form carbon–carbon bonds and carbon–heteroatom bonds.  For example, thionyl chloride can be used to generate and trap the sulfonium ion using chloride as the nucleophile:

text: The thionium ion can be trapped by various intramolecular and intermolecular

text: nucleophile

text: s to form

text: carbon

text: –carbon bonds and carbon–heteroatom bonds.  For example,

text: thionyl chloride

text: can be used to generate and trap the sulfonium ion using chloride as the nucleophile:

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text: The allotropes of carbon include graphite, one of the softest known substances, and diamond, the hardest naturally occurring substance. It bonds readily with other small atoms including other carbon atoms, and is capable of forming multiple stable covalent bonds with suitable, multivalent atoms. Carbon is known to form almost ten million different compounds, a large majority of all chemical compounds. Carbon also has the highest sublimation point of all elements. At atmospheric pressure it has no melting point as its triple point is at 10.8 ± 0.2 MPa and 4,600 ± 300 K (~4,330 °C or 7,820 °F), so it sublimes at about 3,900 K. Graphite is much more reactive than diamond at standard conditions, despite being more thermodynamically stable, as its delocalised pi system is much more vulnerable to attack. For example, graphite can be oxidised by hot concentrated nitric acid at standard conditions to mellitic acid, C(COH), which preserves the hexagonal units of graphite while breaking up the larger structure.

text: The

text: allotropes of carbon

text: include

text: graphite

text: , one of the softest known substances, and

text: diamond

text: , the hardest naturally occurring substance. It

text: bonds

text: readily with other small

text: atom

text: s including other carbon atoms, and is capable of forming multiple stable

text: covalent

text: bonds with suitable, multivalent atoms. Carbon is known to form almost ten million different compounds, a large majority of all

text: chemical compounds

text: . Carbon also has the highest

text: sublimation

text: point of all elements. At

text: atmospheric pressure

text: it has no melting point as its

text: triple point

text: is at 10.8 ± 0.2 MPa and 4,600 ± 300 K (~4,330 °C or 7,820 °F), so it sublimes at about 3,900 K. Graphite is much more reactive than diamond at standard conditions, despite being more thermodynamically stable, as its delocalised

text: pi system

text: is much more vulnerable to attack. For example, graphite can be oxidised by hot concentrated

text: nitric acid

text: at standard conditions to

text: mellitic acid

text: , C(COH), which preserves the hexagonal units of graphite while breaking up the larger structure.

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answers: The allotropes of carbon

answers: NDQ_016396

answers: multiple stable covalent bonds

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answers: a large majority of all chemical compounds

text: Instead of directing equivalent sp orbitals towards all four substituents, shifting s character towards the C-H bonds will stabilize those bonds greatly because of the increased electron density near the carbon, while shifting s character away from the C-F bond will increase its energy by a lesser amount because that bond's electron density is further from the carbon. The atomic s character on the carbon atom has been directed toward the more electropositive hydrogen substituents and away from the electronegative fluorine, which is exactly what Bent's rule suggests.

text: Instead of directing equivalent sp orbitals towards all four substituents, shifting s character towards the C-H bonds will stabilize those bonds greatly because of the increased electron density near the carbon, while shifting s character away from the C-F bond will increase its energy by a lesser amount because that bond's electron density is further from the carbon. The atomic s character on the carbon atom has been directed toward the more electropositive hydrogen substituents and away from the electronegative fluorine, which is exactly what Bent's rule suggests.

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answers: Bent's rule

text: The atom is electrophilic at this time and is attacked by the pi electrons of the alkene [carbon–carbon double bond]. It forms for an instant a single sigma bond to both of the carbon atoms involved. The bonding of bromine is special in this intermediate, due to its relatively large size compared to carbon, the bromide ion is capable of interacting with both carbons which once shared the π-bond, making a three-membered ring. The bromide ion acquires a positive formal charge. At this moment the halogen ion is called a "bromonium ion" or "chloronium ion", respectively.

text: The atom is

text: electrophilic

text: at this time and is attacked by the pi electrons of the alkene [carbon–carbon double bond]. It forms for an instant a single

text: sigma bond

text: to both of the carbon atoms involved. The bonding of

text: bromine

text: is special in this intermediate, due to its relatively large size compared to

text: carbon

text: , the bromide

text: ion

text: is capable of interacting with both carbons which once shared the

text: π-bond

text: , making a three-membered ring. The bromide ion acquires a positive formal charge. At this moment the halogen

text: ion

text: is called a "

text: bromonium ion

text: " or "

text: chloronium ion

text: ", respectively.

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answers: carbon–carbon double bond

text: The atoms of carbon can be bonded together in different ways, termed allotropes of carbon. The best known are graphite, diamond, and amorphous carbon. The physical properties of carbon vary widely with the allotropic form. For example, graphite is opaque and black while diamond is highly transparent. Graphite is soft enough to form a streak on paper (hence its name, from the Greek verb "γράφειν" which means "to write"), while diamond is the hardest naturally occurring material known. Graphite is a good electrical conductor while diamond has a low electrical conductivity. Under normal conditions, diamond, carbon nanotubes, and graphene have the highest thermal conductivities of all known materials. All carbon allotropes are solids under normal conditions, with graphite being the most thermodynamically stable form. They are chemically resistant and require high temperature to react even with oxygen.

text: The atoms of carbon can be bonded together in different ways, termed

text: allotropes of carbon

text: . The best known are

text: graphite

text: diamond

text: , and

text: amorphous carbon

text: . The

text: physical properties

text: of carbon vary widely with the allotropic form. For example, graphite is

text: opaque

text: and black while diamond is highly

text: transparent

text: . Graphite is soft enough to form a streak on paper (hence its name, from the Greek verb "γράφειν" which means "to write"), while diamond is the hardest naturally occurring material known. Graphite is a good

text: electrical conductor

text: while diamond has a low

text: electrical conductivity

text: . Under normal conditions, diamond,

text: carbon nanotube

text: s, and

text: graphene

text: have the highest

text: thermal conductivities

text: of

text: all known materials

text: . All carbon allotropes are solids under normal conditions, with graphite being the most

text: thermodynamically stable

text: form. They are chemically resistant and require high temperature to react even with oxygen.

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answers: All carbon allotropes are solids

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answers: All carbon allotropes are solids

text: One important property of carbon is that it readily forms chains, or networks, that are linked by carbon-carbon (carbon-to-carbon) bonds. The linking process is called polymerization, while the chains, or networks, are called polymers. The source compound is called a monomer.

text: One important property of carbon is that it readily forms chains, or networks, that are linked by carbon-carbon (carbon-to-carbon) bonds. The linking process is called

text: polymerization

text: , while the chains, or networks, are called

text: polymer

text: s. The source compound is called a

text: monomer

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answers: It readily forms chains

text: The carbon atom is assumed to be atomic the center of the tetrahedron. In common use, the four valences of carbon are shown by four bonds around a carbon atom as shown alongside

text: The carbon atom is assumed to be atomic the center of the tetrahedron. In common use, the four valences of carbon are shown by four bonds around a carbon atom as shown alongside

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answers: Tetrahedron

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answers: The carbon atom

text: In 1869, a Russian chemist named Vladimir Markovnikov demonstrated that the addition of HBr to alkenes usually but not always resulted in a specific orientation.  Markovnikov's rule, which stems from these observations, states that in the addition of HBr or another hydrogen halide to an alkene, the acidic proton will add to the less substituted carbon of the double bond. This directed addition of a proton results in the more thermodynamically stable carbocation intermediate, as determined by degrees of substitution; more highly substituted carbocations are stabilized by the electron-pushing inductive effect of the surrounding carbon molecules.

text: In 1869, a

text: Russian

text: chemist named

text: Vladimir Markovnikov

text: demonstrated that the addition of HBr to

text: alkene

text: s usually but not always resulted in a specific orientation.

text: Markovnikov's rule

text: , which stems from these observations, states that in the addition of HBr or another hydrogen

text: halide

text: to an alkene, the acidic

text: proton

text: will add to the less substituted

text: carbon

text: of the

text: double bond

text: . This directed addition of a proton results in the more

text: thermodynamically

text: stable

text: carbocation

text: intermediate, as determined by degrees of substitution; more highly substituted carbocations are stabilized by the electron-pushing inductive effect of the surrounding carbon

text: molecule

text: s.

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answers: alkenes

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answers: double bond

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answers: alkenes

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answers: alkenes

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answers: less substituted carbon

answers: NDQ_016401

answers: alkenes

text: Compounds of carbon are defined as chemical substances containing carbon. More compounds of carbon exist than any other chemical element except for hydrogen. Organic carbon compounds are far more numerous than inorganic carbon compounds. In general bonds of carbon with other elements are covalent bonds. Carbon is tetravalent but carbon free radicals and carbenes occur as short-lived intermediates. Ions of carbon are carbocations and carbanions are also short-lived. An important carbon property is catenation as the ability to form long carbon chains and rings.

text: Compounds of carbon are defined as

text: chemical substances

text: containing

text: carbon

text: . More compounds of carbon exist than any other

text: chemical element

text: except for hydrogen. Organic carbon compounds are far more numerous than inorganic carbon compounds. In general bonds of carbon with other elements are

text: covalent bond

text: s. Carbon is

text: tetravalent

text: but carbon

text: free radicals

text: and

text: carbenes

text: occur as short-lived intermediates. Ions of carbon are

text: carbocations

text: and

text: carbanions

text: are also short-lived. An important carbon property is

text: catenation

text: as the ability to form long carbon chains and rings.

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answers: More compounds of carbon exist than any other chemical element except for hydrogen

answers: NDQ_016396

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answers: More compounds of carbon

text: It is this extremely reactive atomic oxygen species that allows piranha solution to dissolve elemental carbon. Carbon allotropes are difficult to attack chemically because of the highly stable and typically graphite-like hybridized bonds that surface carbon atoms tend to form with each other. The most likely route by which piranha solution disrupts these stable carbon–carbon surface bonds is for an atomic oxygen first to attach directly to a surface carbon to form a carbonyl group:

text: It is this extremely reactive atomic oxygen species that allows piranha solution to dissolve elemental carbon. Carbon

text: allotropes

text: are difficult to attack chemically because of the highly stable and typically graphite-like

text: hybridized bonds

text: that surface carbon atoms tend to form with each other. The most likely route by which piranha solution disrupts these stable carbon–carbon surface bonds is for an atomic oxygen first to attach directly to a surface carbon to form a

text: carbonyl

text: group:

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text: Degradation can also occur as a result of the formation, and then breakage of double bonds, such as solvolysis in PVC(Peacock).  Solvolysis occurs when a Carbon-X bond, with X representing a halogen, is broken. This occurs in PVC in the presence of an acid species. Active Hydrogen atoms will remove a Chlorine atom from the polymer molecule, forming Hydrochloric acid (HCl). The HCl produced may then cause dechlorination of adjacent Carbon atoms. The dechlorinated Carbon atoms then tend to form double bonds, which can be attacked and broken by ozone, just like the degradation of rubbers described above.

text: Degradation can also occur as a result of the formation, and then breakage of double bonds, such as

text: solvolysis

text: in

text: PVC

text: (Peacock).  Solvolysis occurs when a Carbon-X bond, with X representing a halogen, is broken. This occurs in PVC in the presence of an

text: acid

text: species. Active Hydrogen atoms will remove a Chlorine atom from the polymer molecule, forming

text: Hydrochloric acid

text: (HCl). The HCl produced may then cause dechlorination of adjacent Carbon atoms. The dechlorinated

text: Carbon

text: atoms then tend to form double bonds, which can be attacked and broken by ozone, just like the degradation of rubbers described above.

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text: Of the other discovered allotropes, carbon nanofoam is a ferromagnetic allotrope discovered in 1997. It consists of a low-density cluster-assembly of carbon atoms strung together in a loose three-dimensional web, in which the atoms are bonded trigonally in six- and seven-membered rings. It is among the lightest known solids, with a density of about 2 kg/m. Similarly, glassy carbon contains a high proportion of closed porosity, but contrary to normal graphite, the graphitic layers are not stacked like pages in a book, but have a more random arrangement. Linear acetylenic carbon has the chemical structure -(C:::C)-. Carbon in this modification is linear with sp orbital hybridization, and is a polymer with alternating single and triple bonds. This carbyne is of considerable interest to nanotechnology as its Young's modulus is forty times that of the hardest known material – diamond.

text: Of the other discovered allotropes,

text: carbon nanofoam

text: is a

text: ferromagnetic

text: allotrope discovered in 1997. It consists of a low-density cluster-assembly of carbon atoms strung together in a loose three-dimensional web, in which the atoms are bonded trigonally in six- and seven-membered rings. It is among the lightest known solids, with a density of about 2 kg/m. Similarly,

text: glassy carbon

text: contains a high proportion of closed

text: porosity

text: , but contrary to normal graphite, the graphitic layers are not stacked like pages in a book, but have a more random arrangement.

text: Linear acetylenic carbon

text: has the chemical structure -(C:::C)-. Carbon in this modification is linear with sp

text: orbital hybridization

text: , and is a

text: polymer

text: with alternating single and triple bonds. This carbyne is of considerable interest to

text: nanotechnology

text: as its

text: Young's modulus

text: is forty times that of the hardest known material – diamond.

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text: As an alkyne, acetylene is unsaturated because its two carbon atoms are bonded together in a triple bond. The carbon–carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°.

text: As an alkyne, acetylene is

text: unsaturated

text: because its two carbon atoms are

text: bonded

text: together in a

text: triple bond

text: . The carbon–carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°.

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answers: carbon–carbon triple bond

text: During polymerization, a polymer spends most of its time in increasing its chain length, or propagating. After the radical initiator is formed, it attacks a monomer (Figure 11). In an ethene monomer, one electron pair is held securely between the two carbons in a sigma bond. The other is more loosely held in a pi bond. The free radical uses one electron from the pi bond to form a more stable bond with the carbon atom. The other electron returns to the second carbon atom, turning the whole molecule into another radical. This begins the polymer chain. Figure 12 shows how the orbitals of an ethylene monomer interact with a radical initiator.

text: During polymerization, a polymer spends most of its time in increasing its chain length, or propagating. After the

text: radical initiator

text: is formed, it attacks a

text: monomer

text: (Figure 11). In an ethene monomer, one electron pair is held securely between the two carbons in a

text: sigma bond

text: . The other is more loosely held in a

text: pi bond

text: . The free radical uses one electron from the pi bond to form a more stable bond with the carbon atom. The other electron returns to the second carbon atom, turning the whole molecule into another radical. This begins the polymer chain. Figure 12 shows how the orbitals of an ethylene monomer interact with a radical initiator.

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answers: polymerization

text: A carbon atom has four electrons in its outermost valence shell. So, it needs four more electrons to complete its octet. A carbon atom completes its octet only by sharing its valence electrons with other atoms. As a result, a carbon atom forms four covalent bonds by sharing valence electrons with other atoms. This is known as tetravalency of carbon ("tetra" means four). These four valences of carbon are directed towards four corners of a tetrahedron, and inclined to each other atomic an angle of a 109° 28´.

text: A carbon atom has four electrons in its outermost valence shell. So, it needs four more electrons to complete its octet. A carbon atom completes its octet only by sharing its valence electrons with other atoms. As a result, a carbon atom forms four covalent bonds by sharing valence electrons with other atoms. This is known as tetravalency of carbon ("tetra" means four). These four valences of carbon are directed towards four corners of a tetrahedron, and inclined to each other atomic an angle of a 109° 28´.

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracies.

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answers: It can form four covalent bonds

text: Aldehydes feature an sp-hybridized, planar carbon center that is connected by a double bond to oxygen and a single bond to hydrogen. The C–H bond is not ordinarily acidic. Because of resonance stabilization of the conjugate base, an α-hydrogen in an aldehyde (not shown in the picture above) is far more acidic, with a pK near 15, compared to the acidity of a typical alkane (pKa about 50). This acidification is attributed to (i) the electron-withdrawing quality of the formyl center and (ii) the fact that the conjugate base, an enolate anion, delocalizes its negative charge. Related to (i), the aldehyde group is somewhat polar.

text: Aldehydes feature an sp-hybridized, planar carbon center that is connected by a double bond to oxygen and a single bond to hydrogen. The C–H bond is not ordinarily acidic. Because of resonance stabilization of the conjugate base, an

text: α-hydrogen

text: in an aldehyde (not shown in the picture above) is far more

text: acid

text: ic, with a

text: pK

text: near 15, compared to the acidity of a typical

text: alkane

text: (pKa about 50). This acidification is attributed to (i) the electron-withdrawing quality of the formyl center and (ii) the fact that the conjugate base, an

text: enolate

text: anion, delocalizes its negative charge. Related to (i), the aldehyde group is somewhat

text: polar

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answers: Aldehydes

text: It is for this same reason that carbon almost always forms four bonds. Its ground state valence configuration is 2s 2p,   half filled. However, the activation energy to go from half filled to fully filled p orbitals is so small it is negligible, and as such carbon forms them almost instantaneously. Meanwhile, the process releases a significant amount of energy (exothermic). This four equal bond configuration is called sp hybridization.

text: It is for this same reason that

text: carbon

text: almost always forms four

text: bonds

text: . Its ground state

text: valence

text: configuration is 2s 2p,   half filled. However, the

text: activation energy

text: to go from half filled to fully filled p orbitals is so small it is negligible, and as such carbon forms them almost instantaneously. Meanwhile, the process releases a significant amount of energy (

text: exothermic

text: ). This four equal bond configuration is called sp

text: hybridization

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answers: carbon almost always forms four bonds

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answers: four

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answers: It is for this same reason

text: For example, boron–carbon and boron–oxygen bonds are 1.4–1.5 Å and 1.5–1.6 Å in length, respectively, whereas typical metal-carbon and metal-oxygen bonds are 1.9–2.2 Å and 2.0–2.2 Å in length, respectively. The use of boron rather than a metal "tightens" the transition state and gives greater stereoselectivity in the reaction. Thus the above reaction gives a syn:anti ratio of 80:20 using a lithium enolate compared to 97:3 using a bibutylboron enolate.

text: For example, boron–carbon and boron–oxygen bonds are 1.4–1.5

text: Å

text: and 1.5–1.6 Å in length, respectively, whereas typical metal-carbon and metal-oxygen bonds are 1.9–2.2 Å and 2.0–2.2 Å in length, respectively. The use of boron rather than a metal "tightens" the

text: transition state

text: and gives greater stereoselectivity in the reaction. Thus the above reaction gives a syn:anti ratio of 80:20 using a lithium enolate compared to 97:3 using a bibutylboron enolate.

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answers: NDQ_016399

answers: boron–carbon

answers: NDQ_016400

answers: 1.9–2.2

answers: NDQ_016401

answers: boron

text: Similar to carbon–carbon bonds, these bonds can form stable double bonds, as in imines, and triple bonds such as nitriles. Bond lengths range from 147.9 pm for simple amines to 147.5 pm for C-N= compounds such as nitromethane to 135.2 pm for partial double bonds in pyridine to 115.8 pm for triple bonds as in nitriles.

text: Similar to

text: carbon–carbon bond

text: s, these bonds can form stable

text: double bond

text: s, as in

text: imine

text: s, and

text: triple bond

text: s such as

text: nitrile

text: s.

text: Bond length

text: s range from 147.9

text: pm

text: for simple

text: amine

text: s to 147.5 pm for C-N= compounds such as

text: nitromethane

text: to 135.2 pm for partial double bonds in

text: pyridine

text: to 115.8 pm for triple bonds as in

text: nitrile

text: s.

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answers: carbon–carbon bonds

answers: NDQ_016396

answers: triple bonds

answers: NDQ_016398

answers: C-N= compounds

answers: NDQ_016399

answers: nitriles

answers: NDQ_016400

answers: 115.8

answers: NDQ_016401

answers: carbon–carbon bonds

text: An acrylic compound is typically an α,β-unsaturated carbonyl compound: it contains a carbon–carbon double bond and a carbon–oxygen double bond (carbonyl) separated by a carbon–carbon single bond, thus possessing properties characteristic for both functional groups :

text: An acrylic compound is typically an

text: α,β-unsaturated carbonyl compound

text: : it contains a carbon–carbon

text: double bond

text: and a carbon–oxygen double bond (

text: carbonyl

text: ) separated by a carbon–carbon single bond, thus possessing properties characteristic for both functional groups :

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answers: carbonyl

answers: NDQ_016396

answers: double bond

answers: NDQ_016398

answers: Methane

answers: NDQ_016399

answers: carbonyl

answers: NDQ_016400

answers: two

answers: NDQ_016401

answers: carbonyl

text: Most metal carbonyls have 18 valence electrons, and Fe(CO) fits this pattern with 8 valence electrons on Fe and five pairs of electrons provided by the CO ligands.  Reflecting its symmetrical structure and charge neutrality, Fe(CO) is volatile; it is one of the most frequently encountered liquid metal complexes.

text: Most metal carbonyls have

text: 18 valence electrons

text: , and Fe(CO) fits this pattern with 8 valence electrons on Fe and five pairs of electrons provided by the CO ligands.  Reflecting its symmetrical structure and charge neutrality, Fe(CO) is

text: volatile

text: ; it is one of the most frequently encountered liquid metal complexes.

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answers: NDQ_016392

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answers: NDQ_016392

answers: Most metal carbonyls

answers: NDQ_016396

answers: eight valence electrons

answers: NDQ_016398

answers: hydrocarbon

answers: NDQ_016399

answers: Fe(CO)

answers: NDQ_016400

answers: five pairs of electrons

answers: NDQ_016401

answers: most frequently encountered liquid metal complexes

text: The carbon–fluorine bond length is typically about 1.35 ångström (1.39 Å in fluoromethane). It is shorter than any other carbon–halogen bond, and shorter than single carbon–nitrogen and carbon–oxygen bonds, despite fluorine having a larger atomic mass. The short length of the bond can also be attributed to the ionic character/electrostatic attractions between the partial charges on carbon and fluorine. The carbon–fluorine bond length varies by several hundredths of an ångstrom depending on the hybridization of the carbon atom and the presence of other substituents on the carbon or even in atoms farther away. These fluctuations can be used as indication of subtle hybridization changes and stereoelectronic interactions. The table below shows how the average bond length varies in different bonding environments (carbon atoms are sp-hybridized unless otherwise indicated for sp or aromatic carbon).

text: The carbon–fluorine bond length is typically about 1.35

text: ångström

text: (1.39 Å in

text: fluoromethane

text: ). It is shorter than any other carbon–halogen bond, and shorter than single carbon–

text: nitrogen

text: and carbon–

text: oxygen

text: bonds, despite fluorine having a larger

text: atomic mass

text: . The short length of the bond can also be attributed to the ionic character/electrostatic attractions between the partial charges on carbon and fluorine. The carbon–fluorine bond length varies by several hundredths of an ångstrom depending on the hybridization of the carbon atom and the presence of other substituents on the carbon or even in atoms farther away. These fluctuations can be used as indication of subtle hybridization changes and

text: stereoelectronic interaction

text: s. The table below shows how the average bond length varies in different bonding environments (carbon atoms are sp-hybridized unless otherwise indicated for sp or aromatic carbon).

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answers: It is shorter than any other carbon–halogen bond

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answers: It is shorter than any other carbon–halogen bond

text: The configuration of the product is determined by the trajectory of approach of the olefin to the metal carbene. In reactions of monosubstituted metal carbenes with terminal olefins, the olefin likely approaches "end-on" (with the carbon-carbon double bond of the olefin nearly parallel to the metal-carbon double bond of the carbene) with the olefin R group pointed away from the substituent of the carbene. A second transition state model has been proposed for reactions of vinyl-substituted carbenes. In this model, the olefin approaches "side-on" (with the carbon-carbon double bond of the olefin perpendicular to the metal-carbon double bond of the carbene) with the olefin R group far from the vinyl group.

text: The configuration of the product is determined by the trajectory of approach of the olefin to the metal carbene. In reactions of monosubstituted metal carbenes with terminal olefins, the olefin likely approaches "end-on" (with the carbon-carbon double bond of the olefin nearly parallel to the metal-carbon double bond of the carbene) with the olefin R group pointed away from the substituent of the carbene. A second transition state model has been proposed for reactions of vinyl-substituted carbenes. In this model, the olefin approaches "side-on" (with the carbon-carbon double bond of the olefin perpendicular to the metal-carbon double bond of the carbene) with the olefin R group far from the vinyl group.

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answers: Methane

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answers: end-on

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answers: carbon-carbon double bond

text: The lower oxidation state in each of the elements in question has 2 valence electrons in s - orbitals. On the face of it, a simple explanation could be that the valence electrons in an s orbital are more tightly bound and are of lower energy than electrons in p orbitals and therefore less likely to be involved in bonding. Unfortunately this explanation does not stand up. If the total ionization potentials (IP) (see below) of the 2 electrons in s orbitals (the 2nd + 3rd ionization potentials), are examined it can be seen that they increase in the sequence:

text: The lower oxidation state in each of the elements in question has 2 valence electrons in s - orbitals. On the face of it, a simple explanation could be that the valence electrons in an s orbital are more tightly bound and are of lower energy than electrons in p orbitals and therefore less likely to be involved in bonding. Unfortunately this explanation does not stand up. If the total

text: ionization potential

text: s (IP) (see below) of the 2 electrons in s orbitals (the 2nd + 3rd

text: ionization potential

text: s), are examined it can be seen that they increase in the sequence:

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracies.

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text: Key in the bent bond explanation of the gauche effect in difluoroethane is the increased p orbital character of both carbon–fluorine bonds due to the large electronegativity of fluorine.  As a result, electron density builds up above and below to the left and right of the central carbon–carbon bond.  The resulting reduced orbital overlap can be partially compensated when a gauche conformation is assumed, forming a bent bond. Of these two models, hyperconjugation is generally considered the principal cause behind the gauche effect in difluoroethane.

text: Key in the bent bond explanation of the gauche effect in difluoroethane is the increased

text: p orbital

text: character of both carbon–fluorine bonds due to the large electronegativity of fluorine.  As a result, electron density builds up above and below to the left and right of the central carbon–carbon bond.  The resulting reduced orbital overlap can be partially compensated when a gauche conformation is assumed, forming a bent bond. Of these two models, hyperconjugation is generally considered the principal cause behind the gauche effect in difluoroethane.

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answers: large electronegativity of fluorine

text: Alkane conformers arise from rotation around sp hybridised carbon carbon sigma bonds. The smallest alkane with such a chemical bond, ethane, exists as an infinite number of conformations with respect to rotation around the C–C bond. Two of these are recognised as energy minimum (staggered conformation) and energy maximum (eclipsed conformation) forms. The existence of specific conformations is due to hindered rotation around sigma bonds, although a role for hyperconjugation is proposed by a competing theory.

text: Alkane conformers arise from rotation around sp

text: hybridised

text: carbon carbon

text: sigma bond

text: s. The smallest alkane with such a chemical bond,

text: ethane

text: , exists as an infinite number of conformations with respect to rotation around the C–C bond. Two of these are recognised as energy minimum (

text: staggered conformation

text: ) and energy maximum (

text: eclipsed conformation

text: ) forms. The existence of specific conformations is due to hindered rotation around sigma bonds, although a role for

text: hyperconjugation

text: is proposed by a competing theory.

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text: In 1948, it was discovered that allyltrimethylsilane reacts with hydrobromic acid to give (2-bromopropyl)trimethylsilane. Six years later, the generation of (2-iodoethyl)trimethylsilane from vinylsilane and HI was observed. Since then, a number of studies have firmly established the mechanism of electrophilic attack on vinyl- and allylsilanes The electron-releasing strength of the carbon-silicon bond is large, and as a result, the position of silicon in the unsaturated silane controls the site of reaction and stereoselectivity. Formation of the new carbon-carbon bond is at the γ position of allyl silanes and the β position of vinylsilanes. The robustness of silanes makes them amenable to use in synthesis; however, because silicon is less electropositive than other metals employed in electrophilic additions, stronger electrophiles are required.

text: In 1948, it was discovered that allyltrimethylsilane reacts with hydrobromic acid to give (2-bromopropyl)trimethylsilane. Six years later, the generation of (2-iodoethyl)trimethylsilane from vinylsilane and HI was observed. Since then, a number of studies have firmly established the mechanism of electrophilic attack on vinyl- and allylsilanes The electron-releasing strength of the carbon-silicon bond is large, and as a result, the position of silicon in the unsaturated silane controls the site of reaction and stereoselectivity. Formation of the new carbon-carbon bond is at the γ position of allyl silanes and the β position of vinylsilanes. The robustness of silanes makes them amenable to use in synthesis; however, because silicon is less electropositive than other metals employed in electrophilic additions, stronger electrophiles are required.

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text: When ketones are treated with base, enolates can be formed by deprotonation at either α-carbon. The selectivity is determined by both the steric and electronic effects on the α-carbons as well as the precise base used (see figure ""Masked functionality" for regiospecific enolate formation" for an example of this). Enolate formation will be thermodynamically favoured at the most acidic proton which depends on the electronic stabilization of the resulting anion. However, the selectivity can be reversed by sterically hindering the thermodynamic product and therefore kinetically favouring deprotonation at the other α-carbon centre. Traditional methods for regioselective enolate formation use either electronic activating groups (e.g. aldehydes) or steric blocking groups (e.g. 1,2-ethanedithiol protected ketone).

text: When

text: ketones

text: are treated with

text: base

text: , enolates can be formed by

text: deprotonation

text: at either α-carbon. The selectivity is determined by both the

text: steric

text: and

text: electronic effects

text: on the α-carbons as well as the precise base used (see figure ""Masked functionality" for regiospecific enolate formation" for an example of this). Enolate formation will be thermodynamically favoured at the most acidic proton which depends on the electronic stabilization of the resulting

text: anion

text: . However, the selectivity can be reversed by sterically hindering the thermodynamic product and therefore kinetically favouring deprotonation at the other α-carbon centre. Traditional methods for regioselective enolate formation use either electronic activating groups (e.g.

text: aldehydes

text: ) or steric blocking groups (e.g.

text: protected ketone).

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answers: -carbon

text: The carbon–iodine bond is a common functional group that forms part of core organic chemistry; formally, these compounds may be thought of as organic derivatives of the iodide anion. The simplest organoiodine compounds, alkyl iodides, may be synthesised by the reaction of alcohols with phosphorus triiodide; these may then be used in nucleophilic substitution reactions, or for preparing Grignard reagents. The C–I bond is the weakest of all the carbon–halogen bonds due to the minuscule difference in electronegativity between carbon (2.55) and iodine (2.66). As such, iodide is the best leaving group among the halogens, to such an extent that many organoiodine compounds turn yellow when stored over time due to decomposition into elemental iodine; as such, they are commonly used in organic synthesis, because of the easy formation and cleavage of the C–I bond. They are also significantly denser than the other organohalogen compounds thanks to the high atomic weight of iodine. A few organic oxidising agents like the periodinanes contain iodine in a higher oxidation state than −1, such as 2-iodoxybenzoic acid, a common reagent for the oxidation of alcohols to aldehydes, and iodobenzene dichloride (PhICl), used for the selective chlorination of alkenes and alkynes. One of the more well-known uses of organoiodine compounds is the so-called iodoform test, where iodoform (CHI) is produced by the exhaustive iodination of a methyl ketone (or another compound capable of being oxidised to a methyl ketone), as follows:

text: The

text: carbon

text: –iodine bond is a common functional group that forms part of core

text: organic chemistry

text: ; formally, these compounds may be thought of as organic derivatives of the iodide anion. The simplest organoiodine compounds,

text: alkyl iodide

text: s, may be synthesised by the reaction of

text: alcohol

text: s with

text: phosphorus triiodide

text: ; these may then be used in

text: nucleophilic substitution

text: reactions, or for preparing

text: Grignard reagent

text: s. The C–I bond is the weakest of all the carbon–halogen bonds due to the minuscule difference in electronegativity between carbon (2.55) and iodine (2.66). As such, iodide is the best

text: leaving group

text: among the halogens, to such an extent that many organoiodine compounds turn yellow when stored over time due to decomposition into elemental iodine; as such, they are commonly used in

text: organic synthesis

text: , because of the easy formation and cleavage of the C–I bond. They are also significantly denser than the other organohalogen compounds thanks to the high atomic weight of iodine. A few organic oxidising agents like the

text: periodinane

text: s contain iodine in a higher oxidation state than −1, such as

text: 2-iodoxybenzoic acid

text: , a common reagent for the oxidation of alcohols to

text: aldehyde

text: s, and

text: iodobenzene dichloride

text: (PhICl), used for the selective chlorination of

text: alkene

text: s and

text: alkyne

text: s. One of the more well-known uses of organoiodine compounds is the so-called

text: iodoform test

text: , where

text: iodoform

text: (CHI) is produced by the exhaustive iodination of a

text: methyl ketone

text: (or another compound capable of being oxidised to a methyl ketone), as follows:

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answers: 2.55

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answers: C–I bond

answers: NDQ_016400

answers: 2.66

answers: NDQ_016401

answers: The C–I bond is the weakest of all the carbon–halogen bonds

text: Aldehydes and ketones are therefore best used in compartments where such unwanted side reactions are decreased. For experiments with live cells, cell surfaces and extracellular space are typical fielding areas. Nevertheless, a feature of carbonyl groups is the vast number of organic reactions that involve them as electrophiles. Some of these reactions are readily convertible to ligations for probing aldehydes. A rather exotic reaction recently employed for bioconjugation by Agarwal et al. is the adaptation of the Pictet-Spengler-reaction as a ligation. The reaction is known from natural product biosynthetic pathways  and has the major advantage that a new carbon-carbon bond is formed. This guarantees long-term stability compared to carbon-heteroatom bonds at same reaction kinetics.

text: Aldehydes and ketones are therefore best used in compartments where such unwanted side reactions are decreased. For experiments with live cells, cell surfaces and extracellular space are typical fielding areas. Nevertheless, a feature of carbonyl groups is the vast number of organic reactions that involve them as electrophiles. Some of these reactions are readily convertible to ligations for probing aldehydes. A rather exotic reaction recently employed for bioconjugation by Agarwal et al. is the adaptation of the

text: Pictet-Spengler-reaction

text: as a ligation. The reaction is known from natural product biosynthetic pathways  and has the major advantage that a new carbon-carbon bond is formed. This guarantees long-term stability compared to carbon-heteroatom bonds at same reaction kinetics.

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text: The distorted geometry of disilenes can be rationalized by considering the valence orbitals of silicon, which are 3s and 3p, whereas those of carbon are 2s and 2p.  Thus, the energy gap between the ns and np orbitals of a silicon atom is larger than that of a carbon atom.Therefore, silylene fragments are in a singlet state, while carbene fragments are in a triplet state. So, when double bonds are formed by the interaction of these two fragments, disilenes which consist of two silylene units are trans-bending and alkenes which consist of two carbene units are planar.  The bending is even more extreme for the tin analogues of disilenes.

text: The distorted geometry of disilenes can be rationalized by considering the

text: valence

text: orbital

text: s of

text: silicon

text: , which are

text: and

text: , whereas those of

text: carbon

text: are

text: and

text: .  Thus, the energy gap between the

text: ns

text: and

text: np

text: orbital

text: s of a

text: silicon

text: atom

text: is larger than that of a

text: carbon

text: atom

text: .Therefore,

text: silylene

text: fragments are in a

text: singlet

text: state, while

text: carbene

text: fragments are in a

text: triplet

text: state. So, when

text: double bond

text: s are formed by the interaction of these two fragments, disilenes which consist of two

text: silylene

text: units are trans-bending and

text: alkene

text: s which consist of two

text: carbene

text: units are planar.  The bending is even more extreme for the tin analogues of disilenes.

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text: Pincer complexes have been shown to participate in a variety of transformations, such as the activation of CO, N, carbon-halogen bond formation and oxidative addition of carbon-oxygen and carbon-fluorine bonds, polymerization of alkenes and alkynes, alkane dehydrogenation and alkane metathesis, and transfer hydrogen catalysis. They have also recently been studied for their use as molecular sensors and switches.

text: Pincer complexes have been shown to participate in a variety of transformations, such as the activation of CO, N, carbon-halogen bond formation and oxidative addition of carbon-oxygen and carbon-fluorine bonds, polymerization of

text: alkenes

text: and

text: alkynes

text: , alkane

text: dehydrogenation

text: and

text: alkane metathesis

text: , and transfer hydrogen

text: catalysis

text: . They have also recently been studied for their use as molecular sensors and switches.

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text: As a group, they are generally divided into monosaccharides, oligosaccharides, and polysaccharides depending on the number of sugar subunits. Maltose is an oligosaccharide, specifically a disaccharide, formed by the union of two glucose units (monosaccharide). Glucose is classified as a hexose because it is composed of six carbons. The two glucoses which compose maltose are cyclized in pyran form and are joined by an O-glycosidic bond through the first carbon (C) of the first glucose and fourth carbon (C) of the second glucose, indicated as (1 → 4). The link is characterized as α due to the O-glycosidic bond to the anomeric carbon (C) being in the opposite plane from the  substituent in the same ring (C of the first glucose). If the O-glycosidic bond to the anomeric carbon (C) was in the same plane as the  substituent, it would be classified as a β(1 → 4) bond, and the resulting molecule would be cellobiose.  The anomeric carbon (C) of the second glucose molecule, the (C) that is not involved in an O-glycosidic bond, could be either an α- or β-anomer depending on the bond direction of the attached hydroxyl group relative to the  substituent of the same ring, resulting in either α-maltose or β-maltose.

text: As a group, they are generally divided into

text: monosaccharide

text: s,

text: oligosaccharide

text: s, and

text: polysaccharide

text: s depending on the number of sugar subunits. Maltose is an oligosaccharide, specifically a disaccharide, formed by the union of two glucose units (

text: monosaccharide

text: ). Glucose is classified as a

text: hexose

text: because it is composed of six carbons. The two glucoses which compose maltose are cyclized in pyran form and are joined by an

text: O-glycosidic bond

text: through the first carbon (C) of the first

text: glucose

text: and fourth carbon (C) of the second

text: glucose

text: , indicated as (1 → 4). The link is characterized as α due to the O-glycosidic bond to the anomeric carbon (C) being in the opposite plane from the

text: substituent

text: in the same ring (C of the first glucose). If the O-glycosidic bond to the anomeric carbon (C) was in the same plane as the  substituent, it would be classified as a β(1 → 4) bond, and the resulting molecule would be

text: cellobiose

text: .  The anomeric carbon (C) of the second glucose molecule, the (C) that is not involved in an O-glycosidic bond, could be either an α- or β-anomer depending on the bond direction of the attached hydroxyl group relative to the  substituent of the same ring, resulting in either α-maltose or β-maltose.

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracy.

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answers: (1  4)

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answers: NDQ_016399

answers: cellobiose

answers: NDQ_016400

answers: four

answers: NDQ_016401

answers: polysaccharides

text: The full biosynthesis of Absinthin in Artemisia absinthium has not been elucidated, but a great portion of it can be inferred from the natural product precursors required to access Absinthin. While terpenoids like Absinthin can be said to consist of isoprene "units," isoprene by itself is unstable and does not react directly. Rather, the isoprene units are transferred and reacted as diphosphates. As the nomenclature for terpenes suggests, the first Absinthin precursor farnesyl diphosphate [A] contains 15 carbons, or 3 isoprene units. Diphosphate departure (1) generates a carbo-cation within the synthase, which can then be attacked by a carbon-carbon double bond at the opposing end of the molecule (2). The first stable intermediate in the biosynthesis pathway in Artemisia is likely Germacrene A [B], which has been previously identified in plant sesquiterpene pathways as a precursor to guaianolides. From there, hydroxylation (3) occurs, followed by oxidation (4) to an aldehyde directly followed by further hydroxylation (5) and formation of a carboxyl group. It is important to note the disappearance of the terminal carbon-carbon double bond after (4), as the reduction of this bond in the final product differentiates the Absinthin monomer from other Germacrene A downstream products. This reduction does not necessarily occur at step (4), but may occur further downstream. With the carboxyl and hydroxyl group in position, the guaiano-lactone [C] formation via dehydration (7) can occur, as proposed for a general guaianolide pathway. Formation of the Absinthin sesquiterpene guaianolide monomer [D] from hydroxylation and double bond rearrangement (8,9) is then postulated to directly precede dimerization to Absinthin [E] via a naturally occurring Diels-Alder reaction [10], which is likely facilitated by the associated synthase even though the reaction itself can occur in good yields spontaneously, albeit slower than typical natural product biosynthesis.

text: The full biosynthesis of Absinthin in

text: Artemisia absinthium

text: has not been elucidated, but a great portion of it can be inferred from the natural product precursors required to access Absinthin. While terpenoids like Absinthin can be said to consist of

text: isoprene

text: "units,"

text: isoprene

text: by itself is unstable and does not react directly. Rather, the isoprene units are transferred and reacted as diphosphates. As the nomenclature for terpenes suggests, the first Absinthin precursor

text: farnesyl diphosphate

text: Diels-Alder

text: reaction [10], which is likely facilitated by the associated synthase even though the reaction itself can occur in good yields spontaneously, albeit slower than typical natural product biosynthesis.

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answers: carbon double bond

text: For this molecule, carbon sp hybridises, because one π (pi) bond is required for the double bond between the carbons and only three σ bonds are formed per carbon atom. In sp hybridisation the 2s orbital is mixed with only two of the three available 2p orbitals,

text: For this molecule, carbon sp hybridises, because one

text: π (pi) bond

text: is required for the

text: double bond

text: between the carbons and only three σ bonds are formed per carbon atom. In sp hybridisation the 2s orbital is mixed with only two of the three available 2p orbitals,

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answers: carbon atoms

text: The type of bonding can be explained in terms of orbital hybridization. In ethylene each carbon atom has three sp orbitals and one p-orbital. The three sp orbitals lie in a plane with ~120° angles. The p-orbital is perpendicular to this plane. When the carbon atoms approach each other, two of the sp orbitals overlap to form a sigma bond. At the same time, the two p-orbitals approach (again in the same plane) and together they form a pi-bond. For maximum overlap, the p-orbitals have to remain parallel, and, therefore, rotation around the central bond is not possible. This property gives rise to cis-trans isomerism. Double bonds are shorter than single bonds because p-orbital overlap is maximized.

text: The type of bonding can be explained in terms of

text: orbital hybridization

text: . In

text: ethylene

text: each carbon atom has three

text: sp

text: orbitals and one

text: p-orbital

text: . The three sp orbitals lie in a plane with ~120° angles. The p-orbital is perpendicular to this plane. When the carbon atoms approach each other, two of the sp orbitals overlap to form a

text: sigma bond

text: . At the same time, the two p-orbitals approach (again in the same plane) and together they form a

text: pi-bond

text: . For maximum overlap, the p-orbitals have to remain parallel, and, therefore, rotation around the central bond is not possible. This property gives rise to

text: cis-trans isomerism

text: . Double bonds are shorter than single bonds because p-orbital overlap is maximized.

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answers: ethylene

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answers: three sp orbitals

answers: NDQ_016401

answers: ethylene

text: resulting in two sp orbitals and two remaining p orbitals. The chemical bonding in acetylene (ethyne) (CH) consists of sp–sp overlap between the two carbon atoms forming a σ bond and two additional π bonds formed by p–p overlap. Each carbon also bonds to hydrogen in a σ s–sp overlap at 180° angles.

text: resulting in two sp orbitals and two remaining p orbitals. The chemical bonding in

text: acetylene

text: (ethyne) (CH) consists of sp–sp overlap between the two carbon atoms forming a σ bond and two additional

text: π bonds

text: formed by p–p overlap. Each carbon also bonds to hydrogen in a σ s–sp overlap at 180° angles.

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answers: (CH)

answers: NDQ_016396

answers: two additional  bonds

answers: NDQ_016398

answers: Hydrocarbon

answers: NDQ_016399

answers: ethyne

answers: NDQ_016400

answers: two remaining p orbitals

answers: NDQ_016401

answers: Carbon can form more compounds than any other element

text: Nickel–Catalyzed Carbon–Carbon Bond Formation.  The majority of the transformations under investigation are carbon–carbon bond–forming reactions promoted by nickel catalysts. We have discovered a variety of coupling reactions to join a number of different functional groups in highly regio–, stereo– and enantioselective fashion depending on the nature of the supporting ligands on nickel.

text: Nickel–Catalyzed Carbon–Carbon Bond Formation.  The majority of the transformations under investigation are carbon–carbon bond–forming reactions promoted by nickel catalysts. We have discovered a variety of coupling reactions to join a number of different functional groups in highly regio–, stereo– and enantioselective fashion depending on the nature of the supporting ligands on nickel.

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answers: Carbon–Carbon Bond Formation

answers: NDQ_016396

answers: regio–, stereo– and enantioselective

answers: NDQ_016398

answers: Methane

answers: NDQ_016399

answers: Carbon–Carbon Bond Formation

answers: NDQ_016400

answers: three

answers: NDQ_016401

answers: Carbon–Carbon Bond Formation

text: The driving force for this reaction is the formation of an electrophile X that forms a covalent bond with an electron-rich unsaturated C=C bond. The positive charge on X is transferred to the carbon-carbon bond, forming a carbocation during the formation of the C-X bond.

text: The driving force for this reaction is the formation of an

text: electrophile

text: X that forms a

text: covalent bond

text: with an electron-rich

text: unsaturated

text: C=C bond. The positive charge on X is transferred to the carbon-carbon bond, forming a

text: carbocation

text: during the formation of the C-X bond.

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answers: carbon

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answers: unsaturated C=C bond

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answers: hydrocarbon

answers: NDQ_016399

answers: C=C

answers: NDQ_016400

answers: electron-rich

answers: NDQ_016401

answers: carbon

text: Two atoms can be bonded by sharing more than one pair of electrons. The common bonds to carbon are single, double and triple bonds. Single bonds are most common and are represented by a single, solid line between two atoms in a skeletal formula. Double bonds are denoted by two parallel lines, and triple bonds are shown by three parallel lines.

text: Two atoms can be bonded by sharing more than one pair of electrons. The common bonds to carbon are single, double and triple bonds. Single bonds are most common and are represented by a single, solid line between two atoms in a skeletal formula. Double bonds are denoted by two parallel lines, and triple bonds are shown by three parallel lines.

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answers: Single bonds are most common

answers: NDQ_016396

answers: three

answers: NDQ_016398

answers: Hydrocarbons

answers: NDQ_016399

answers: triple bonds

answers: NDQ_016400

answers: three

answers: NDQ_016401

answers: Single bonds are most common

text: The position of the carbon-carbon double bonds in carboxylic acid chains in fats is designated by Greek letters. The carbon atom closest to the carboxyl group is the alpha carbon, the next carbon is the beta carbon and so on. In fatty acids the carbon atom of the methyl group at the end of the hydrocarbon chain is called the omega carbon because omega is the last letter of the Greek alphabet. Omega-3 fatty acids have a double bond three carbons away from the methyl carbon, whereas omega-6 fatty acids have a double bond six carbons away from the methyl carbon. The illustration below shows the omega-6 fatty acid, linoleic acid.

text: The position of the carbon-carbon double bonds in

text: carboxylic acid

text: chains in fats is designated by

text: Greek letters

text: . The carbon atom closest to the

text: carboxyl group

text: is the alpha carbon, the next carbon is the beta carbon and so on. In fatty acids the carbon atom of the

text: methyl group

text: at the end of the hydrocarbon chain is called the omega carbon because omega is the last letter of the Greek alphabet.

text: Omega-3 fatty acid

text: s have a double bond three carbons away from the methyl carbon, whereas

text: omega-6 fatty acid

text: s have a double bond six carbons away from the methyl carbon. The illustration below shows the omega-6 fatty acid,

text: linoleic acid

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answers: Omega-3 fatty acids

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answers: Omega-3 fatty acids

text: The carbon-carbon bonds along the cyclohexane ring are sp³ hybrid orbitals, which have tetrahedral symmetry. Therefore, the angles between bonds of a tetravalent carbon atom have a preferred value θ ≈ 109.5°. The bonds also have a fairly fixed bond length λ. On the other hand, adjacent carbon atoms are free to rotate about the axis of the bond. Therefore, a ring that is warped so that the bond lengths and angles are close to those ideal values will have less strain energy than a flat ring with 120° angles.For each particular conformation of the carbon ring, the directions of the 12 carbon-hydrogen bonds (and therefore the positions of the hydrogen atoms) are fixed.

text: The carbon-carbon bonds along the cyclohexane ring are sp³

text: hybrid orbitals

text: , which have

text: tetrahedral

text: symmetry. Therefore, the angles between bonds of a

text: tetravalent

text: carbon atom have a preferred value θ ≈ 109.5°. The bonds also have a fairly fixed

text: bond length

text: λ. On the other hand, adjacent carbon atoms are free to rotate about the axis of the bond. Therefore, a ring that is warped so that the bond lengths and angles are close to those ideal values will have less strain energy than a flat ring with 120° angles.For each particular conformation of the carbon ring, the directions of the 12 carbon-hydrogen bonds (and therefore the positions of the hydrogen atoms) are fixed.

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answers: tetravalent carbon atom

text: As shown in Eq. 2, the neutral pathway of the Heck reaction begins with the oxidative addition of the aryl or alkenyl halide into a coordinatively unsaturated palladium(0) complex (typically bound to two phosphine ligands) to give complex I. Dissociation of a phosphine ligand followed by association of the alkene yields complex II, and migratory insertion of the alkene into the carbon-palladium bond establishes the key carbon-carbon bond. Insertion takes place in a suprafacial fashion, but the dihedral angle between the alkene and palladium-carbon bond during insertion can vary from 0° to ~90°. After insertion, β-hydride elimination affords the product and a palladium(II)-hydrido complex IV, which is reduced by base back to palladium(0).

text: As shown in Eq. 2, the neutral pathway of the Heck reaction begins with the oxidative addition of the aryl or alkenyl halide into a coordinatively unsaturated palladium(0) complex (typically bound to two phosphine ligands) to give complex I. Dissociation of a phosphine ligand followed by association of the alkene yields complex II, and migratory insertion of the alkene into the carbon-palladium bond establishes the key carbon-carbon bond. Insertion takes place in a suprafacial fashion, but the dihedral angle between the alkene and palladium-carbon bond during insertion can vary from 0° to ~90°. After insertion, β-hydride elimination affords the product and a palladium(II)-hydrido complex IV, which is reduced by base back to palladium(0).

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answers: carbon

text: The methyl group carbon atom has six valence electrons from its bonds to the hydrogen atoms because carbon is more electronegative than hydrogen. Also, one electron is gained from its bond with the other carbon atom because the electron pair in the C−C bond is split equally. It therefore has a total of seven electrons, whereas a neutral carbon atom would have four valence electrons because carbon is in group 14 of the periodic table. The difference, 4 − 7 = −3, is the oxidation state of that carbon atom.  That is, if it is assumed that all the bonds were 100% ionic (which in fact they are not), the carbon would be described as .

text: The

text: methyl

text: group carbon atom has six valence electrons from its bonds to the hydrogen atoms because carbon is more electronegative than hydrogen. Also, one electron is gained from its bond with the other carbon atom because the electron pair in the

text: C−C bond

text: is split equally. It therefore has a total of seven electrons, whereas a neutral carbon atom would have four valence electrons because carbon is in

text: group 14

text: of the periodic table. The difference, 4 − 7 = −3, is the oxidation state of that carbon atom.  That is, if it is assumed that all the bonds were 100% ionic (which in fact they are not), the carbon would be described as .

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answers: methyl group

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answers: methyl group

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answers: C C bond

answers: NDQ_016401

answers: carbon is more electronegative than hydrogen

text: Most commonly fullerene ligands behave similarly to electron-deficient alkenes such as tetracyanoethylene. Thus, they coordinate in a dihapto fashion. This binding occurs on the junction points of two 6-membered rings. Hexahapto and pentahapto bonding is rarely present in these systems. Evidence against this lies in alternating bond lengths of the bonded ring carbons. What instead occurs, is multiple dihapto bonding. This can be observed with the ruthenium complex below:

text: Most commonly fullerene ligands behave similarly to

text: electron-deficient

text: alkene

text: s such as

text: tetracyanoethylene

text: . Thus, they coordinate in a

text: dihapto

text: fashion. This binding occurs on the junction points of two 6-membered rings. Hexahapto and pentahapto bonding is rarely present in these systems. Evidence against this lies in alternating

text: bond length

text: s of the bonded ring carbons. What instead occurs, is multiple dihapto bonding. This can be observed with the

text: ruthenium

text: complex below:

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answers: 0

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracies.

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answers: 0

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answers: carbon

answers: NDQ_016396

answers: 6-membered rings

answers: NDQ_016398

answers: alkenes

answers: NDQ_016399

answers: Hexahapto

answers: NDQ_016400

answers: 6

answers: NDQ_016401

answers: carbon

text: A push-pull olefin is a type of olefin characterized by an electron-withdrawing substituent on one side of the double bond and an electron-donating substituent on the other side. This makes the pi bond very polarized. The rotational barrier for a push-pull olefin is lower than that of an ordinary olefin and this makes it an interesting candidate for a molecular switch for instance azobenzenes. A push-pull configuration also helps to stabilize the double bond because the carbon-carbon bond has considerably less double bond character. For instance cyclobutadiene is a very unstable molecule but with both olefinic bonds in push-pull configuration (two ester substituents and two tertiary amine substituents) the molecule is stable indeed.

text: A push-pull olefin is a type of

text: olefin

text: characterized by an

text: electron-withdrawing

text: substituent

text: on one side of the

text: double bond

text: and an electron-donating substituent on the other side. This makes the

text: pi bond

text: very

text: polarized

text: . The

text: rotational barrier

text: for a push-pull olefin is lower than that of an ordinary

text: olefin

text: and this makes it an interesting candidate for a

text: molecular switch

text: for instance

text: azobenzene

text: s. A push-pull configuration also helps to stabilize the double bond because the carbon-carbon bond has considerably less double bond character. For instance

text: cyclobutadiene

text: is a very unstable molecule but with both olefinic bonds in push-pull configuration (two

text: ester

text: substituents and two

text: tertiary amine

text: substituents) the molecule is stable indeed.

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answers: NDQ_016392

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answers: carbon

answers: NDQ_016396

answers: double bond

answers: NDQ_016398

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answers: cyclobutadiene

answers: NDQ_016400

answers: two

answers: NDQ_016401

answers: carbon

text: The diagram above shows the rhodium–carbon ( inside pentagons on the left) and carbon–carbon ( outside pentagons on the left) bond distances for both ligands, along with the bond angles ( inside pentagons on the right) within each cyclopentadienyl ring. The atom labels used are the same as those shown in the crystal structure above. Within the unsubstituted cyclopentadienyl ligand, the carbon–carbon bond lengths vary between 1.35 Å and 1.40 Å and the internal bond angles vary between 107° and 109°. For comparison, the internal angle at each vertex of a regular pentagon is 108°. The rhodium–carbon bond lengths vary between 2.16 Å and 2.18 Å. These results are consistent with η-coordination of the ligand to the metal centre. In the case of the substituted cyclopentadienyl ligand, there is somewhat greater variation: carbon–carbon bond lengths vary between 1.39 Å and 1.48 Å, the internal bond angles vary between 106° and 111°, and the rhodium–carbon bond lengths vary between 2.14 Å and 2.20 Å. The greater variation in the substituted ligand is attributed to the distortions necessary to relieve the steric strain imposed by neighbouring tert-butyl substituents; despite these variations, the data demonstrate that the substituted cyclopentadienyl is also η-coordinated.

text: The diagram above shows the rhodium–carbon ( inside pentagons on the left) and carbon–carbon ( outside pentagons on the left) bond distances for both ligands, along with the bond angles ( inside pentagons on the right) within each cyclopentadienyl ring. The atom labels used are the same as those shown in the crystal structure above. Within the unsubstituted cyclopentadienyl ligand, the carbon–carbon bond lengths vary between 1.35 Å and 1.40 Å and the internal bond angles vary between 107° and 109°. For comparison, the internal angle at each vertex of a

text: regular pentagon

text: is 108°. The rhodium–carbon bond lengths vary between 2.16 Å and 2.18 Å. These results are consistent with η-coordination of the ligand to the metal centre. In the case of the substituted cyclopentadienyl ligand, there is somewhat greater variation: carbon–carbon bond lengths vary between 1.39 Å and 1.48 Å, the internal bond angles vary between 106° and 111°, and the rhodium–carbon bond lengths vary between 2.14 Å and 2.20 Å. The greater variation in the substituted ligand is attributed to the distortions necessary to relieve the steric strain imposed by neighbouring tert-butyl substituents; despite these variations, the data demonstrate that the substituted cyclopentadienyl is also η-coordinated.

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answers: -coordination

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracies.

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answers: 0: The answer is not relevant or complete at all.

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answers: 0

answers: tqa2:L_0821/T_4205/9f66cbb8c53bdb4f26597fe69958eef0

answers: 0: The answer is not relevant or complete at all.

answers: NDQ_016392

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answers: carbon–carbon bond lengths

answers: NDQ_016396

answers: between 1.35  and 1.40

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answers: Hydrocarbon

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answers: unsubstituted

answers: NDQ_016400

answers: rhodium

answers: NDQ_016401

answers: It can form many compounds

text: Intramolecular reactions of diazocarbonyl compounds include addition to carbon–carbon double bonds to form fused cyclopropanes and insertion into carbon–hydrogen bonds or carbon–carbon bonds.

text: Intramolecular reactions of diazocarbonyl compounds include addition to

text: carbon–carbon double bonds

text: to form fused

text: cyclopropanes

text: and insertion into

text: carbon–hydrogen bond

text: s or

text: carbon–carbon bond

text: s.

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answers: carbon–hydrogen bonds

text: The Weinreb–Nahm amide has since been adopted into regular use by organic chemists as a dependable method for the synthesis of ketones. These functional groups are present in a large number of natural products and can be reliably reacted to form new carbon–carbon bonds or converted into other functional groups. This method has been used in a number of syntheses, including Macrosphelides A and B, Amphidinolide J, and Spirofungins A and B. (See Scope below)

text: The Weinreb–Nahm amide has since been adopted into regular use by organic chemists as a dependable method for the synthesis of ketones. These

text: functional group

text: s are present in a large number of

text: natural product

text: s and can be reliably reacted to form new carbon–carbon bonds or converted into other functional groups. This method has been used in a number of syntheses, including Macrosphelides A and B, Amphidinolide J, and Spirofungins A and B. (See

text: Scope

text: below)

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answers: Amphidinolide J

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answers: three

answers: NDQ_016401

answers: ketones

text: ALOX15 and Alox15 enzymes are non-heme, iron-containing dioxygenases.  They commonly catalyze the attachment of molecular oxygen  as a peroxy residue to polyunsaturated fatty acids (PUFA) that contain two carbon-carbon double bonds that for the human ALOX15 are located between carbons 10 and 9 and 7 and 6 as numbered counting backward from the last or omega (i.e. ω) carbon at the methyl end of the PUFA (these carbons are also termed ω-10 and ω-9 and ω-7 and ω-6).  In PUFAs that do not have a third carbon-carbon double bound between their ω-13 and ω-12 carbons, human ALOX15 forms ω-6 peroxy intermediates; in PUFAs that do have this third double bound, human ALOX15 makes the ω-6 peroxy intermediate but also small amounts of the ω-9 peroxy intermediate. Rodent Alox15 enzymes, in contrast, produce almost exclusively ω-9 peroxy intermediates. Concurrently, ALOX15 and rodent Alox15 enzymes rearrange the carbon-carbon double bonds to bring them into the 1S-hydroxy-2E,4Z-diene configuration. ALOX15 and Alox15 enzymes act with a high degree of Stereospecificity to form products that position the hydroperoxy residue in the S stereoisomer configuration.

text: ALOX15 and Alox15 enzymes are non-heme, iron-containing

text: dioxygenase

text: s.  They commonly catalyze the attachment of molecular oxygen  as a

text: peroxy

text: residue to

text: polyunsaturated fatty acids

text: (PUFA) that contain two carbon-carbon

text: double bond

text: s that for the human ALOX15 are located between carbons 10 and 9 and 7 and 6 as numbered counting backward from the last or omega (i.e. ω) carbon at the methyl end of the PUFA (these carbons are also termed ω-10 and ω-9 and ω-7 and ω-6).  In PUFAs that do not have a third carbon-carbon double bound between their ω-13 and ω-12 carbons, human ALOX15 forms ω-6 peroxy intermediates; in PUFAs that do have this third double bound, human ALOX15 makes the ω-6 peroxy intermediate but also small amounts of the ω-9 peroxy intermediate. Rodent Alox15 enzymes, in contrast, produce almost exclusively ω-9 peroxy intermediates. Concurrently, ALOX15 and rodent Alox15 enzymes rearrange the carbon-carbon double bonds to bring them into the 1S-hydroxy-2E,4Z-

text: diene

text: configuration. ALOX15 and Alox15 enzymes act with a high degree of

text: Stereospecificity

text: to form products that position the hydroperoxy residue in the S

text: stereoisomer

text: configuration.

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answers: double bonds

answers: NDQ_016398

answers: hydroperoxy

answers: NDQ_016399

answers: polyunsaturated fatty acids

answers: NDQ_016400

answers: two carbon-carbon double bonds

answers: NDQ_016401

answers: carbon

text: The reducing end of a disaccharide is the monosaccharide with a free anomeric carbon that is not involved in a glycosidic bond and is thus capable of converting to the open-chain form. Recall that disaccharides consist of two monosaccharides and may be either reducing or nonreducing. However, even a reducing disaccharide will only have one reducing end, as disaccharides are held together by glycosidic bonds, which consist of at least one anomeric carbon. With one anomeric carbon unable to convert to the open-chain form, only the free anomeric carbon is available to reduce another compound. A nonreducing disaccharide has both anomeric carbons tied up in the glycosidic bond.

text: The reducing end of a disaccharide is the monosaccharide with a free

text: anomeric carbon

text: that is not involved in a glycosidic bond and is thus capable of converting to the open-chain form. Recall that disaccharides consist of two monosaccharides and may be either reducing or nonreducing. However, even a reducing disaccharide will only have one reducing end, as disaccharides are held together by glycosidic bonds, which consist of at least one anomeric carbon. With one anomeric carbon unable to convert to the open-chain form, only the free anomeric carbon is available to reduce another compound. A nonreducing disaccharide has both anomeric carbons tied up in the glycosidic bond.

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answers: Anomeric carbon

text: Example: The quantum numbers used to refer to the outermost valence electrons of the Carbon (C) atom, which are located in the 2p atomic orbital, are; n = 2 (2nd electron shell),  = 1 (p orbital subshell), m = 1, 0 or −1, m = ½ (parallel spins).

text: Example: The quantum numbers used to refer to the outermost

text: valence

text: electron

text: s of the

text: Carbon

text: (C)

text: atom

text: , which are located in the 2p

text: atomic orbital

text: , are; n = 2 (2nd electron shell),  = 1 (p orbital

text: subshell

text: ), m = 1, 0 or −1, m = ½ (parallel spins).

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answers: Carbon (C) atom

text: The high electronegativity of fluorine (4.0 for F vs. 2.5 for carbon) gives the carbon–fluorine bond a significant polarity/dipole moment. The electron density is concentrated around the fluorine, leaving the carbon relatively electron poor. This introduces ionic character to the bond through partial charges (C—F). The partial charges on the fluorine and carbon are attractive, contributing to the unusual bond strength of the carbon–fluorine bond. The bond is labeled as "the strongest in organic chemistry," because fluorine forms the strongest single bond to carbon. Carbon–fluorine bonds can have a bond dissociation energy (BDE) of up to 544 kJ/mol. The BDE (strength of the bond) is higher than other carbon–halogen and carbon–hydrogen bonds. For example, the molecule represented by CHX has a BDE of 115 kcal/mol for carbon–fluorine while values of 104.9, 83.7, 72.1, and 57.6 kcal/mol represent carbon–X bonds to hydrogen, chlorine, bromine, and iodine, respectively.

text: The high

text: electronegativity

text: of fluorine (4.0 for F vs. 2.5 for carbon) gives the carbon–fluorine bond a significant

text: polarity

text: dipole moment

text: . The electron density is concentrated around the fluorine, leaving the carbon relatively electron poor. This introduces ionic character to the bond through

text: partial charges

text: (C—F). The partial charges on the fluorine and carbon are attractive, contributing to the unusual bond strength of the carbon–fluorine bond. The bond is labeled as "the strongest in organic chemistry," because fluorine forms the strongest single bond to carbon. Carbon–fluorine bonds can have a

text: bond dissociation energy

text: (BDE) of up to 544 kJ/mol. The BDE (strength of the bond) is higher than other carbon–

text: halogen

text: and carbon–

text: hydrogen

text: bonds. For example, the molecule represented by CHX has a BDE of 115 kcal/mol for carbon–fluorine while values of 104.9, 83.7, 72.1, and 57.6 kcal/mol represent carbon–X bonds to

text: hydrogen

text: chlorine

text: bromine

text: , and

text: iodine

text: , respectively.

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answers: carbon–fluorine bonds

text: The central carbon of allene forms two sigma bonds and two pi bonds. The central carbon is sp-hybridized, and the two terminal carbons are sp-hybridized. The bond angle formed by the three carbons is 180°, indicating linear geometry for the carbons of allene. It can also be viewed as an "extended tetrahedral" with a similar shape to methane.

text: The central carbon of allene forms two

text: sigma bond

text: s and two

text: pi bond

text: s. The central carbon is

text: sp-hybridized

text: , and the two terminal carbons are

text: sp-hybridized

text: . The bond angle formed by the three carbons is 180°, indicating linear geometry for the carbons of allene. It can also be viewed as an "extended tetrahedral" with a similar shape to

text: methane

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answers: Carbon can form more compounds than any other element

text: Some examples of reactions which form carbon–carbon bonds are aldol reactions, Diels–Alder reaction, the addition of a Grignard reagent to a carbonyl group, a Heck reaction, a Michael reaction and a Wittig reaction.

text: Some examples of reactions which form carbon–carbon bonds are

text: aldol reaction

text: s,

text: Diels–Alder reaction

text: , the addition of a

text: Grignard reagent

text: to a

text: carbonyl group

text: , a

text: Heck reaction

text: , a

text: Michael reaction

text: and a

text: Wittig reaction

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answers: carbonyl group

text: two carbon–oxygen–phosphorus bondings, no phosphorus–oxygen double bonds but one phosphorus–carbon bond in phosphonites,

text: two carbon–oxygen–phosphorus bondings, no phosphorus–oxygen double bonds but one phosphorus–carbon bond in phosphonites,

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answers: phosphonites

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answers: carbon

text: Carbon is ordinarily classified as a nonmetal but has some metallic properties and is occasionally classified as a metalloid. Hexagonal graphitic carbon (graphite) is the most thermodynamically stable allotrope of carbon under ambient conditions. It has a lustrous appearance and is a fairly good electrical conductor. Graphite has a layered structure. Each layer comprises carbon atoms bonded to three other carbon atoms in a honeycomb lattice arrangement. The layers are stacked together and held loosely by van der Waals forces and delocalized valence electrons.

text: Carbon is ordinarily classified as a nonmetal but has some metallic properties and is occasionally classified as a metalloid.

text: Hexagonal graphitic carbon

text: (graphite) is the most thermodynamically stable

text: allotrope

text: of carbon under ambient conditions. It has a lustrous appearance and is a fairly good electrical conductor. Graphite has a layered structure. Each layer comprises carbon atoms bonded to three other carbon atoms in a

text: honeycomb lattice

text: arrangement. The layers are stacked together and held loosely by

text: van der Waal

text: s forces and

text: delocalized valence electrons

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answers: ordinarily classified as a nonmetal

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answers: Graphite

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answers: Hexagonal graphitic carbon

text: where R and R′ can be, but are not limited to, an alkyl, aryl, alkynyl, allyl, halogen, or pseudo-halogen group. The reaction is usually an irreversible process due to thermodynamic and kinetic reasons. Thermodynamics will favor the reaction based on the electronegativities of the metals and kinetics will favor the reaction if there are empty orbitals on both metals. There are different types of transmetalation including redox-transmetalation and redox-transmetalation/ligand exchange. During transmetalation the metal-carbon bond is activated, leading to the formation of new metal-carbon bonds. Transmetalation is commonly used in catalysis, synthesis of main group complexes, and synthesis of transition metal complexes.

text: where R and R′ can be, but are not limited to, an

text: alkyl

text: aryl

text: alkynyl

text: allyl

text: halogen

text: , or

text: pseudo-halogen

text: group. The reaction is usually an

text: irreversible process

text: due to

text: thermodynamic

text: and kinetic reasons. Thermodynamics will favor the reaction based on the

text: electronegativities

text: of the metals and

text: kinetics

text: will favor the reaction if there are empty orbitals on both metals. There are different types of transmetalation including redox-transmetalation and redox-transmetalation/ligand exchange. During transmetalation the metal-carbon bond is activated, leading to the formation of new metal-carbon bonds. Transmetalation is commonly used in

text: catalysis

text: , synthesis of

text: main group

text: complexes, and synthesis of

text: transition metal

text: complexes.

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answers: Transmetalation

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answers: The metal-carbon bond is activated

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answers: Carbon can form more compounds than any other element

text: Unsaturated hydrocarbons are hydrocarbons that have double or triple covalent bonds between adjacent carbon atoms.  Those with at least one carbon-to-carbon double bond are called alkenes and those with at least one carbon-to-carbon triple bond are called alkynes. The position of the double or triple bond is shown by a number  written either at the start of the name, or just before the -ene or -yne suffix (e.g. pent-2-ene and 2-butyne). The number represents the position of the first of the two carbons making the bond, in the longest carbon chain.  Alkenes and alkynes with more than one double or triple bond respectively are named with a prefix preceding the -ene or -yne (e.g. 2,4-pentadiene).

text: Unsaturated hydrocarbons are

text: hydrocarbon

text: s that have double or triple

text: covalent bond

text: s between adjacent

text: carbon

text: atom

text: s.  Those with at least one carbon-to-carbon double bond are called

text: alkene

text: s and those with at least one carbon-to-carbon triple bond are called alkynes. The position of the double or triple bond is shown by a number  written either at the start of the name, or just before the -ene or -yne suffix (e.g. pent-2-ene and 2-butyne). The number represents the position of the first of the two carbons making the bond, in the longest carbon chain.  Alkenes and alkynes with more than one double or triple bond respectively are named with a prefix preceding the -ene or -yne (e.g. 2,4-pentadiene).

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answers: Alkenes and alkynes

text: The study of arsabenzene and related compounds was an important step in the understanding of compounds that contain multiple bonds between carbon and heavier elements.

text: The study of arsabenzene and related compounds was an important step in the understanding of compounds that contain

text: multiple bond

text: s between carbon and heavier elements.

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answers: carbon

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answers: arsabenzene

text: Quantum mechanically, the lowest energy is obtained if the four bonds are equivalent, which requires that they are formed from equivalent orbitals on the carbon. A set of four equivalent orbitals can be obtained that are linear combinations of the valence-shell (core orbitals are almost never involved in bonding) s and p wave functions, which are the  four sp hybrids.

text: Quantum mechanically, the lowest energy is obtained if the four bonds are equivalent, which requires that they are formed from equivalent orbitals on the carbon. A set of four equivalent orbitals can be obtained that are linear combinations of the valence-shell (core orbitals are almost never involved in bonding) s and p wave functions, which are the  four sp hybrids.

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text: The carbon–carbon bond distances are 1.40 Å within the five-membered rings, and the Fe–C bond distances are 2.04 Å.  Although X-ray crystallography (in the monoclinic space group) points to the Cp rings being in a staggered conformation, it has been shown through gas phase electron diffraction and computational studies that in the gas phase the Cp rings are eclipsed. The staggered conformation is believed to be most stable in the condensed phase due to crystal packing. The point group of the staggered conformation is D and the point group of the eclipsed conformation is D.

text: The carbon–carbon bond distances are 1.40 Å within the five-membered rings, and the Fe–C bond distances are 2.04 Å.  Although

text: X-ray crystallography

text: (in the monoclinic space group) points to the Cp rings being in a staggered conformation, it has been shown through gas phase electron diffraction and computational studies that in the gas phase the Cp rings are eclipsed. The staggered conformation is believed to be most stable in the condensed phase due to crystal packing. The point group of the staggered conformation is D and the point group of the eclipsed conformation is D.

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text: As predicted by the VSEPR model of electron pair repulsion, the molecular geometry of alkenes includes bond angles about each carbon in a double bond of about 120°. The angle may vary because of steric strain introduced by nonbonded interactions between functional groups attached to the carbons of the double bond. For example, the C–C–C bond angle in propylene is 123.9°.

text: As predicted by the

text: VSEPR

text: model of

text: electron

text: pair repulsion, the

text: molecular geometry

text: of alkenes includes

text: bond angle

text: s about each carbon in a double bond of about 120°. The angle may vary because of

text: steric strain

text: introduced by

text: nonbonded interactions

text: between

text: functional group

text: s attached to the carbons of the double bond. For example, the C–C–C bond angle in

text: propylene

text: is 123.9°.

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answers: alkenes

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text: The carbon–fluorine bond is a polar covalent bond between carbon and fluorine that is a component of all organofluorine compounds. It is the second strongest single bond in organic chemistry—behind the Si-F single bond, and relatively short—due to its partial ionic character. The bond also strengthens and shortens as more fluorines are added to the same carbon on a chemical compound. As such, fluoroalkanes like tetrafluoromethane (carbon tetrafluoride) are some of the most unreactive organic compounds.

text: The carbon–fluorine bond is a

text: polar covalent bond

text: between

text: carbon

text: and

text: fluorine

text: that is a component of all

text: organofluorine compound

text: s. It is the second strongest single bond in

text: organic chemistry

text: —behind the Si-F single bond, and relatively short—due to its partial

text: ionic

text: character. The bond also strengthens and shortens as more fluorines are added to the same carbon on a

text: chemical compound

text: . As such,

text: fluoroalkanes

text: like

text: tetrafluoromethane

text: (carbon tetrafluoride) are some of the most

text: unreactive

text: organic compounds.

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answers: It is the second strongest single bond

text: For example, acetone, the active ingredient in some nail polish removers, has a net dipole associated with the carbonyl (see figure 2). Since oxygen is more electronegative than the carbon that is covalently bonded to it, the electrons associated with that bond will be closer to the oxygen than the carbon, creating a partial negative charge (δ) on the oxygen, and a partial positive charge (δ) on the carbon. They are not full charges because the electrons are still shared through a covalent bond between the oxygen and carbon. If the electrons were no longer being shared, then the oxygen-carbon bond would be an electrostatic interaction.

text: For example,

text: acetone

text: , the active ingredient in some nail polish removers, has a net dipole associated with the

text: carbonyl

text: (see figure 2). Since oxygen is more electronegative than the carbon that is covalently bonded to it, the electrons associated with that bond will be closer to the oxygen than the carbon, creating a partial negative charge (δ) on the oxygen, and a partial positive charge (δ) on the carbon. They are not full charges because the electrons are still shared through a covalent bond between the oxygen and carbon. If the electrons were no longer being shared, then the oxygen-carbon bond would be an electrostatic interaction.

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answers: It can form more compounds than any other element

text: Carborane acid consists of 11 boron atoms; each boron atom is bound to a chlorine atom. The chlorine atoms serve to enhance acidity and act as shields against attacks from the outside due to the steric hindrance they form around the cluster. The cluster, consisting of the 11 borons, 11 chlorines, and a single carbon atom, is paired with a hydrogen atom [Figure 1], bound to the carbon atom. The boron and carbon atoms are allowed to form six bonds due to boron’s ability to form a special kind of bond called “three-center-two-electron bond”  [Figure 4].

text: Carborane acid consists of 11 boron atoms; each boron atom is bound to a chlorine atom. The chlorine atoms serve to enhance acidity and act as shields against attacks from the outside due to the steric hindrance they form around the cluster. The cluster, consisting of the 11 borons, 11 chlorines, and a single carbon atom, is paired with a hydrogen atom [Figure 1], bound to the carbon atom. The boron and carbon atoms are allowed to form six bonds due to boron’s ability to form a special kind of bond called “three-center-two-electron bond”  [Figure 4].

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answers: Carbon can form more compounds than any other element

text: Graphyne is a theorized allotrope of carbon. Its structure is one-atom-thick planar sheets of sp and sp-bonded carbon atoms arranged in crystal lattice. It can be seen as a lattice of benzene rings connected by acetylene bonds. Depending on the content of acetylene groups, graphyne can be considered a mixed hybridization, sp, where 1 < n < 2, and thus differs from the hybridization of graphene (considered pure sp) and diamond (pure sp).

text: Graphyne is a theorized

text: allotrope

text: of

text: carbon

text: . Its structure is one-atom-thick

text: planar

text: sheets of sp and

text: sp-bonded

text: carbon atoms arranged in crystal lattice. It can be seen as a lattice of

text: benzene

text: rings connected by

text: acetylene

text: bonds. Depending on the content of acetylene groups, graphyne can be considered a mixed hybridization, sp, where 1 < n < 2, and thus differs from the hybridization of

text: graphene

text: (considered pure sp) and

text: diamond

text: (pure sp).

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text: This enzyme belongs to the family of hydrolases, those acting on carbon-nitrogen bonds other than peptide bonds, specifically in nitriles.  The systematic name of this enzyme class is arylacetonitrile aminohydrolase. This enzyme participates in cyanoamino acid metabolism.

text: This enzyme belongs to the family of

text: hydrolase

text: s, those acting on carbon-nitrogen bonds other than peptide bonds, specifically in nitriles.  The

text: systematic name

text: of this enzyme class is arylacetonitrile aminohydrolase. This enzyme participates in

text: cyanoamino acid metabolism

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text: In the periodic table, some of the elements adjacent to the commonly recognised metalloids, although usually classified as either metals or nonmetals, are occasionally referred to as near-metalloids or noted for their metalloidal character. To the left of the metal–nonmetal dividing line, such elements include gallium, tin and bismuth. They show unusual packing structures, marked covalent chemistry (molecular or polymeric), and amphoterism. To the right of the dividing line are carbon, phosphorus, selenium and iodine. They exhibit metallic lustre, semiconducting properties and bonding or valence bands with delocalized character. This applies to their most thermodynamically stable forms under ambient conditions: carbon as graphite; phosphorus as black phosphorus; and selenium as grey selenium.

text: In the periodic table, some of the elements adjacent to the commonly recognised metalloids, although usually classified as either metals or nonmetals, are occasionally referred to as near-metalloids or noted for their metalloidal character. To the left of the metal–nonmetal dividing line, such elements include gallium, tin and bismuth. They show unusual packing structures, marked covalent chemistry (molecular or polymeric), and amphoterism. To the right of the dividing line are carbon, phosphorus, selenium and iodine. They exhibit metallic lustre, semiconducting properties and bonding or valence bands with delocalized character. This applies to their most thermodynamically stable forms under ambient conditions: carbon as graphite; phosphorus as black phosphorus; and selenium as grey selenium.

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text: Structures containing covalent bonds can be treated using the ionic model providing they satisfy the topological conditions given above, but a special situation applies to hydrocarbons which allows the bond valence model to be reduced to the traditional bond model of organic chemistry.  If an atom has a valence, V,  that is equal to its coordination number, N, its bonding strength according to Eq. 3 is exactly 1.0 vu (valence units), a condition that greatly simplifies the model.  This condition is obeyed by carbon, hydrogen and silicon.  Since these atoms all have bonding strengths of 1.0 vu the bonds between them are all predicted to have integral valences with carbon forming four single bonds and hydrogen one.  Under these conditions, the bonds are all single bonds (or multiples of single bonds).  Compounds can be constructed by linking carbon and hydrogen atoms with bonds that are all exactly equivalent.  Under certain conditions, nitrogen can form three bonds and oxygen two, but since nitrogen and oxygen typically also form hydrogen bonds, the resulting N-H and O-H bonds have valences less than 1.0 vu, leading through the application of Eq. 1, to the C-C and C-H bonds having valences that differ from 1.0 vu.  Nevertheless, the simple bonding rules of organic chemistry are still good approximations, though the rules of the bond valence model are better.

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answers: hydrogen

text: The same internal stress that benefits the hardness of DLC materials makes it difficult to bond such coatings to the substrates to be protected. The internal stresses try to "pop" the DLC coatings off of the underlying samples. This challenging downside of extreme hardness is answered in several ways, depending upon the particular "art" of the production process. The most simple is to exploit the natural chemical bonding that happens in cases in which incident carbon ions supply the material to be impacted into sp bonded carbon atoms and the impacting energies that are compressing carbon volumes condensed earlier. In this case the first carbon ions will impact the surface of the item to be coated. If that item is made of a carbide-forming substance such as Ti or Fe in steel a layer of carbide will be formed that is later bonded to the DLC grown on top of it. Other methods of bonding include such strategies as depositing intermediate layers that have atomic spacings that grade from those of the substrate to those characteristic of sp bonded carbon. In 2006 there were as many successful recipes for bonding DLC coatings as there were sources of DLC.

text: The same internal stress that benefits the hardness of DLC materials makes it difficult to bond such coatings to the substrates to be protected. The internal stresses try to "pop" the DLC coatings off of the underlying samples. This challenging downside of extreme hardness is answered in several ways, depending upon the particular "art" of the production process. The most simple is to exploit the natural chemical bonding that happens in cases in which incident carbon ions supply the material to be impacted into sp bonded carbon atoms and the impacting energies that are compressing carbon volumes condensed earlier. In this case the first carbon ions will impact the surface of the item to be coated. If that item is made of a

text: carbide

text: -forming substance such as

text: Ti

text: or

text: Fe

text: in

text: steel

text: a layer of carbide will be formed that is later bonded to the DLC grown on top of it. Other methods of bonding include such strategies as depositing intermediate layers that have atomic spacings that grade from those of the substrate to those characteristic of sp bonded carbon. In 2006 there were as many successful recipes for bonding DLC coatings as there were sources of DLC.

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answers: DLC materials

text: Here, the carbene intermediate inserts into a carbon-hydrogen bond to form the carbon-carbon bond needed to close the cyclopentene ring.  Carbene insertions into carbon-hydrogen bonds can also occur intermolecularly:

text: Here, the carbene intermediate inserts into a carbon-hydrogen bond to form the carbon-carbon bond needed to close the cyclopentene ring.

text: Carbene insertions into carbon-hydrogen bonds

text: can also occur intermolecularly:

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracies.

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answers: carbon

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answers: carbon-carbon bond

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answers: cyclopentene

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answers: carbon

text: 1-Dodecene is an alkene with the formula CHCH=CH, consisting of a chain of twelve carbon atoms terminating with a double bond.  While there are many isomers of dodecene depending on which carbon the double bond is placed, this isomer is of greater commercial importance.  It is classified as an alpha-olefin.  Alpha-olefins are distinguished by having a double bond at the primary or alpha (α) position. This location of a double bond enhances the reactivity of the compound and makes it useful for a number of applications, especially for the production of detergents.

text: 1-Dodecene is an

text: alkene

text: with the formula CHCH=CH, consisting of a chain of twelve carbon atoms terminating with a

text: double bond

text: .  While there are many isomers of dodecene depending on which carbon the double bond is placed, this isomer is of greater commercial importance.  It is classified as an

text: alpha-olefin

text: .  Alpha-olefins are distinguished by having a double bond at the primary or alpha (α) position. This location of a double bond enhances the reactivity of the compound and makes it useful for a number of applications, especially for the production of

text: detergent

text: s.

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answers: carbon atoms

text: Bond length can be determined between different elements in molecules by using the atomic radii of the atom. Carbon bonds with itself to form two covalent network solids.  Diamond's C-C bond has a distance of 0.142 nm away from each Carbon, while looking at Graphite's C-C bond has a distance of 0.341 nm away from each Carbon. Although both bonds are between the same molecule they can still have different bond length.

text: Bond length

text: can be determined between different elements in molecules by using the atomic radii of the atom. Carbon bonds with itself to form two covalent network solids.  Diamond's C-C bond has a distance of 0.142 nm away from each Carbon, while looking at Graphite's C-C bond has a distance of 0.341 nm away from each Carbon. Although both bonds are between the same molecule they can still have different bond length.

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answers: Carbon bonds with itself

text: CO, ,  and  are isoelectronic because each has two nuclei and 10 valence electrons, with each atom considered to have 5 of them (a lone-pair and a triple-bond). Isoelectronicity does not relate to formal charge on the atoms in a structure: these all have the same configuration even though carbon monoxide has formal charges that are balanced (:C≡O:) whereas dinitrogen has each atom neutral (:NN:) and nitrosonium has an overall net charge.

text: CO

text: , ,  and  are isoelectronic because each has two nuclei and 10 valence electrons, with each atom considered to have 5 of them (a lone-pair and a triple-bond). Isoelectronicity does not relate to

text: formal charge

text: on the atoms in a structure: these all have the same configuration even though carbon monoxide has formal charges that are balanced (:C≡O:) whereas dinitrogen has each atom neutral (:NN:) and nitrosonium has an overall net charge.

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text: These results can be predicted with FMO theory by observing the interaction between the HOMO and LUMO of the species. To use FMO theory, the reaction should be considered as two separate ideas: (1) whether or not the reaction is allowed, and (2) which mechanism the reaction proceeds though. In the case of a [1,5] shift on pentadiene, the HOMO of the sigma bond (i.e. a constructive bond) and the LUMO of butadiene on the remaining 4 carbons is observed. Assuming the reaction happens suprafacially, the shift results with the HOMO of butadiene on the 4 carbons that are not involved in the sigma bond of the product. Since the pi system changed from the LUMO to the HOMO, this reaction is allowed (though it would not be allowed if the pi system went from LUMO to LUMO).

text: These results can be predicted with FMO theory by observing the interaction between the HOMO and LUMO of the species. To use FMO theory, the reaction should be considered as two separate ideas: (1) whether or not the reaction is allowed, and (2) which mechanism the reaction proceeds though. In the case of a [1,5] shift on pentadiene, the HOMO of the sigma bond (i.e. a constructive bond) and the LUMO of butadiene on the remaining 4 carbons is observed. Assuming the reaction happens suprafacially, the shift results with the HOMO of butadiene on the 4 carbons that are not involved in the sigma bond of the product. Since the pi system changed from the LUMO to the HOMO, this reaction is allowed (though it would not be allowed if the pi system went from LUMO to LUMO).

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answers: LUMO

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answers: LUMO

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answers: pentadiene

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answers: LUMO of butadiene on the remaining 4 carbons

text: Acetylene molecule: Each carbon atom has four electrons in its outermost shell and each hydrogen atom has only one electron in its outermost shell. Two carbon atoms share two electrons each with hydrogen atoms to form single bonds. Each carbon then requires three more electrons to acquire a stable configuration of the nearest noble gas (neon). This is done by mutually sharing three pairs of electrons between the two carbon atoms to form a triple bond.

text: Acetylene

text: molecule: Each carbon atom has four electrons in its outermost shell and each hydrogen atom has only one electron in its outermost shell. Two carbon atoms share two electrons each with hydrogen atoms to form single bonds. Each carbon then requires three more electrons to acquire a stable configuration of the nearest noble gas (neon). This is done by mutually sharing three pairs of electrons between the two carbon atoms to form a triple bond.

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answers: Acetylene

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answers: three pairs

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answers: Hydrocarbon

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answers: Acetylene

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answers: three pairs

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answers: Carbon can form more compounds than any other element.

text: Direct metalation through C-H bond activation or C-H oxidative addition is one method often utilized.  Activation of a C‒H bond leads to oxidative addition of the carbene ligand to the metal center.  Typically, direct metalation requires the blockage of sites that would lead to normal NHC complexes — phenyl and isopropyl groups are good blocking substituents, as discussed earlier.  Smaller substituents may be cleaved.  Direct metalation by silver(I) with imidazolium salts can cause cleavage at the C2 position if methyl is used as the blocking group.  The result is formation of normal NHC carbenes.  n-alkyl and benzyl groups may undergo the same fate as the methyl group.  Steric bulk may also influence the formation of MIC complexes over NHC complexes.  For imidazolium salts, the C2 position may not need to be blocked if the nitrogen substituents (N1 or N3) are sterically-demanding.  Interactions between the nitrogen substituents and the metal center prevent normal NHC complexes from forming.  If the carbene is part of a bidentate ligand with a forced geometry, the MIC complex may form preferentially as well.  The counteranion of imidazolium salts participates in NHC vs. MIC formation.  NHC formation typically occurs by heterolytic bond cleavage, so small, coordinating anions favor this pathway.  MIC formation typically occurs by an oxidative addition pathway, so non-coordinating and apolar anions are preferred, such as BF or SbF.  Other techniques focus on the activation of the desired carbon rather than blocking undesired carbons.  A carbon may be activated by a halogen.  A C-X bond (X = halide) is more favorable for activation than a C-H bond.  This pathway results in the oxidative addition of the MIC carbene halide to a low valent metal center.

text: Direct

text: metalation

text: through

text: C-H bond activation

text: or

text: C-H oxidative addition

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracies.

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answers: Carbene ligand to the metal center

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answers: C-H

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answers: NHC carbenes

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answers: metal center

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answers: Carbenes

text: Carbon–hydrogen bond functionalization (C–H functionalization) is a type of reaction in which a carbon–hydrogen bond is cleaved and replaced with a carbon-X bond (where X is usually carbon, oxygen, or nitrogen).  The term usually implies that a transition metal is involved in the C-H cleavage process. Reactions classified by the term typically involve the hydrocarbon first to react with a metal catalyst to create an organometallic complex in which the hydrocarbon is coordinated to the inner-sphere of a metal, either via an intermediate "alkane or arene complex" or as a transition state leading to a "M−C" intermediate. The intermediate of this first step (known as C-H activation and sometimes used interchangeably with C-H functionalization) can then undergo subsequent reactions to produce the functionalized product. Important to this definition is the requirement that during the C–H cleavage event, the hydrocarbyl species remains associated in the inner-sphere and under the influence of "M".

text: Carbon–hydrogen bond functionalization (C–H functionalization) is a type of reaction in which a

text: carbon–hydrogen bond

text: is cleaved and replaced with a carbon-X bond (where X is usually carbon, oxygen, or nitrogen).  The term usually implies that a transition metal is involved in the C-H cleavage process. Reactions classified by the term typically involve the

text: hydrocarbon

text: first to react with a metal catalyst to create an

text: organometallic

text: complex in which the hydrocarbon is

text: coordinated

text: to the inner-sphere of a metal, either via an intermediate "alkane or

text: arene

text: complex" or as a

text: transition state

text: leading to a "M−C" intermediate. The intermediate of this first step (known as C-H activation and sometimes used interchangeably with C-H functionalization) can then undergo subsequent reactions to produce the functionalized product. Important to this definition is the requirement that during the C–H cleavage event, the hydrocarbyl species remains associated in the inner-sphere and under the influence of "M".

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answers: hydrocarbyl

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answers: carbon

text: In most organic elimination reactions, at least one hydrogen is lost to form the double bond: the unsaturation of the molecule increases.  It is also possible that a molecule undergoes reductive elimination, by which the valence of an atom in the molecule decreases by two, though this is more common in inorganic chemistry.  An important class of elimination reactions is those involving alkyl halides, with good leaving groups, reacting with a Lewis base to form an alkene.  Elimination may be considered the reverse of an addition reaction. When the substrate is asymmetric, regioselectivity is determined by Zaitsev's rule or through Hofmann elimination if the carbon with the most substituted hydrogen is inaccessible.

text: In most organic elimination reactions, at least one hydrogen is lost to form the double bond: the

text: unsaturation

text: of the molecule increases.  It is also possible that a molecule undergoes

text: reductive elimination

text: , by which the valence of an atom in the molecule decreases by two, though this is more common in inorganic chemistry.  An important class of elimination reactions is those involving

text: alkyl halide

text: s, with good

text: leaving group

text: s, reacting with a

text: Lewis base

text: to form an

text: alkene

text: .  Elimination may be considered the reverse of an

text: addition reaction

text: . When the substrate is asymmetric,

text: regioselectivity

text: is determined by

text: Zaitsev's rule

text: or through

text: Hofmann elimination

text: if the carbon with the most substituted hydrogen is inaccessible.

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text: Bond formation between carbon atoms forms very thermodynamically stable products. Therefore, they often require the use of a catalyst to improve kinetics and ensure reversibility.

text: Bond formation between carbon atoms forms very thermodynamically stable products. Therefore, they often require the use of a catalyst to improve kinetics and ensure reversibility.

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answers: Carbon atoms

text: The term agostic is reserved to describe two-electron, three-center bonding interactions between carbon, hydrogen, and a metal. Two-electron three-center bonding is clearly implicated in the complexation of H, e.g., in W(CO)(PCy)H, which is closely related to the agostic complex shown in the figure. Silane binds to metal centers often via agostic-like, three-centered Si┄H−M interactions.  Because these interactions do not include carbon, however, they are not classified as agostic.

text: The term agostic is reserved to describe two-electron, three-center bonding interactions between carbon, hydrogen, and a metal. Two-electron three-center bonding is clearly implicated in the complexation of H, e.g., in W(CO)(PCy)H, which is closely related to the agostic complex shown in the figure.

text: Silane

text: binds to metal centers often via agostic-like, three-centered Si┄H−M interactions.  Because these interactions do not include carbon, however, they are not classified as agostic.

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answers: Silane

text: In Group 14 elements (the carbon group), lone pairs can manifest themselves by shortening or lengthening single (bond order 1) bond lengths, as well as in the effective order of triple bonds as well. The familiar alkynes have a carbon-carbon triple bond (bond order 3) and a linear geometry of 180° bond angles (figure A in reference ). However, further down in the group (silicon, germanium, and tin), formal triple bonds have an effective bond order 2 with one lone pair (figure B) and trans-bent geometries. In lead, the effective bond order is reduced even further to a single bond, with two lone pairs for each lead atom (figure C).  In the organogermanium compound (Scheme 1 in the reference), the effective bond order is also 1, with complexation of the acidic isonitrile (or isocyanide) C-N groups, based on interaction with germanium's empty 4p orbital.

text: In

text: Group 14

text: elements (the

text: carbon group

text: ), lone pairs can manifest themselves by shortening or lengthening single (

text: bond order

text: 1) bond lengths, as well as in the effective order of triple bonds as well. The familiar

text: alkyne

text: s have a carbon-carbon triple bond (

text: bond order

text: 3) and a linear geometry of 180° bond angles (figure A in reference ). However, further down in the group (

text: silicon

text: germanium

text: , and

text: tin

text: ), formal triple bonds have an effective bond order 2 with one lone pair (figure B) and

text: trans

text: -bent geometries. In

text: lead

text: , the effective bond order is reduced even further to a single bond, with two lone pairs for each lead atom (figure C).  In the

text: organogermanium compound

text: (Scheme 1 in the reference), the effective bond order is also 1, with complexation of the

text: acidic

text: isonitrile

text: (or isocyanide) C-N groups, based on interaction with germanium's empty 4p orbital.

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answers: carbon

text: Each carbon of the double bond uses its three sp hybrid orbitals to form sigma bonds to three atoms (the other carbon and two hydrogen atoms). The unhybridized 2p atomic orbitals, which lie perpendicular to the plane created by the axes of the three sp² hybrid orbitals, combine to form the pi bond. This bond lies outside the main C–C axis, with half of the bond on one side of the molecule and half on the other.

text: Each carbon of the double bond uses its three sp

text: hybrid orbitals

text: to form sigma bonds to three atoms (the other carbon and two hydrogen atoms). The unhybridized 2p atomic orbitals, which lie perpendicular to the plane created by the axes of the three sp² hybrid orbitals, combine to form the pi bond. This bond lies outside the main C–C axis, with half of the bond on one side of the molecule and half on the other.

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answers: carbon

text: Depurination is not uncommon because purine is a good leaving group via the 9N-nitrogen (see the structure of a purine). Furthermore, the anomeric carbon is especially reactive towards nucleophilic substitution (effectively making the carbon-oxygen bond shorter, stronger and more polar, while making the carbon-purine bond longer and weaker). This makes the bond especially susceptible to hydrolysis.

text: Depurination is not uncommon because purine is a good

text: leaving group

text: via the 9N-nitrogen (see the structure of a

text: purine

text: ). Furthermore, the

text: anomeric carbon

text: is especially reactive towards

text: nucleophilic substitution

text: (effectively making the carbon-oxygen bond shorter, stronger and more polar, while making the carbon-purine bond longer and weaker). This makes the bond especially susceptible to hydrolysis.

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answers: shorter, stronger and more polar

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answers: The bond especially susceptible to hydrolysis

text: Chemical structure refers to both molecular geometry and electronic structure. The structure can be represented by a variety of diagrams called structural formulas. Lewis structures use a dot notation to represent the valence electrons for an atom; these are the electrons that determine the role of the atom in chemical reactions. Bonds between atoms can be represented by lines with one line for each pair of electrons that is shared. In a simplified version of such a diagram, called a skeletal formula, only carbon-carbon bonds and functional groups are shown.

text: Chemical structure refers to both molecular geometry and electronic structure. The structure can be represented by a variety of diagrams called

text: structural formula

text: s.

text: Lewis structure

text: s use a dot notation to represent the

text: valence electron

text: s for an atom; these are the electrons that determine the role of the atom in chemical reactions. Bonds between atoms can be represented by lines with one line for each pair of electrons that is shared. In a simplified version of such a diagram, called a

text: skeletal formula

text: , only carbon-carbon bonds and functional groups are shown.

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answers: carbon-carbon bonds and functional groups

text: The molecular structure of the alkanes directly affects their physical and chemical characteristics. It is derived from the electron configuration of carbon, which has four valence electrons. The carbon atoms in alkanes are always sp hybridized, that is to say that the valence electrons are said to be in four equivalent orbitals derived from the combination of the 2s orbital and the three 2p orbitals. These orbitals, which have identical energies, are arranged spatially in the form of a tetrahedron, the angle of cos(−) ≈ 109.47° between them.

text: The molecular structure of the alkanes directly affects their physical and chemical characteristics. It is derived from the

text: electron configuration

text: of

text: carbon

text: , which has four

text: valence electron

text: s. The carbon atoms in alkanes are always

text: sp hybridized

text: , that is to say that the valence electrons are said to be in four equivalent orbitals derived from the combination of the 2s orbital and the three 2p orbitals. These orbitals, which have identical energies, are arranged spatially in the form of a

text: tetrahedron

text: , the angle of cos(−) ≈ 109.47° between them.

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text: Carbon is the sixth element, with a ground-state electron configuration of 1s2s2p, of which the four outer electrons are valence electrons. Its first four ionisation energies, 1086.5, 2352.6, 4620.5 and 6222.7 kJ/mol, are much higher than those of the heavier group 14 elements. The electronegativity of carbon is 2.5, significantly higher than the heavier group 14 elements (1.8–1.9), but close to most of the nearby nonmetals as well as some of the second- and third-row transition metals. Carbon's covalent radii are normally taken as 77.2 pm (C–C), 66.7 pm (C=C) and 60.3 pm (C≡C), although these may vary depending on coordination number and what the carbon is bonded to. In general, covalent radius decreases with lower coordination number and higher bond order.

text: Carbon is the sixth element, with a ground-state

text: electron configuration

text: of 1s2s2p, of which the four outer electrons are

text: valence electron

text: s. Its first four ionisation energies, 1086.5, 2352.6, 4620.5 and 6222.7 kJ/mol, are much higher than those of the heavier group 14 elements. The electronegativity of carbon is 2.5, significantly higher than the heavier group 14 elements (1.8–1.9), but close to most of the nearby nonmetals as well as some of the second- and third-row

text: transition metal

text: s. Carbon's

text: covalent radii

text: are normally taken as 77.2 pm (C–C), 66.7 pm (C=C) and 60.3 pm (C≡C), although these may vary depending on coordination number and what the carbon is bonded to. In general, covalent radius decreases with lower coordination number and higher bond order.

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answers: In general, covalent radius decreases with lower coordination number and higher bond order

text: The types of bonding can be explained through in terms of orbital hybridization. In the case of acetylene each carbon atom has two sp orbitals and two p-orbitals. The two sp orbitals  are linear with 180° angles and occupy the x-axis (cartesian coordinate system). The p-orbitals are perpendicular on the y-axis and the z-axis.  When the carbon atoms approach each other the sp orbitals overlap to form a sp-sp sigma bond. At the same time the p-orbitals approach and together they form a p-p pi-bond. Likewise, the other pair of p-orbitals form a  p-p pi-bond. The result is formation of one sigma bond and two pi bonds.

text: The types of bonding can be explained through in terms of

text: orbital hybridization

text: . In the case of acetylene each carbon atom has two

text: sp orbital

text: s and two

text: p-orbital

text: s. The two sp orbitals  are linear with 180° angles and occupy the x-axis (

text: cartesian coordinate system

text: ). The p-orbitals are

text: perpendicular

text: on the y-axis and the z-axis.  When the carbon atoms approach each other the sp orbitals overlap to form a sp-sp

text: sigma bond

text: . At the same time the p-orbitals approach and together they form a p-p

text: pi-bond

text: . Likewise, the other pair of p-orbitals form a  p-p pi-bond. The result is formation of one sigma bond and two pi bonds.

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text: X-ray diffraction confirms that all six carbon-carbon bonds in benzene are the same length, 140 pm (1.40 Å) – intermediate between the bond lengths of single (154 pm) and double (134 pm) carbon-carbon bonds.  This is consistent with delocalization of the electrons from the double bonds in Kekulé's structures equally between each of the six carbon atoms which form a planar ring.  The molecular orbital theory description involves the formation of three delocalized π orbitals spanning all six carbon atoms, while the valence bond theory description involves a superposition of resonance structures.  This electronic structure provides benzene with unusual stability and contributes to the molecular and chemical properties which are now known as aromaticity.  To accurately reflect the nature of the bonding as having neither single nor double bonds, but rather something in between, benzene is often depicted with a circle inside a hexagonal arrangement of carbon atoms, similar to the structure first illustrated by Thiele.

text: X-ray diffraction

text: confirms that all six carbon-carbon bonds in benzene are the same length, 140

text: pm

text: Å

text: ) – intermediate between the

text: bond length

text: s of single (154 pm) and double (134 pm) carbon-carbon bonds.  This is consistent with

text: delocalization

text: of the electrons from the double bonds in Kekulé's structures equally between each of the six carbon atoms which form a planar ring.  The

text: molecular orbital theory

text: description involves the formation of three delocalized

text: π orbitals

text: spanning all six carbon atoms, while the

text: valence bond theory

text: description involves a superposition of resonance structures.  This electronic structure provides benzene with unusual stability and contributes to the molecular and chemical properties which are now known as

text: aromaticity

text: .  To accurately reflect the nature of the bonding as having neither single nor double bonds, but rather something in between, benzene is often depicted with a circle inside a hexagonal arrangement of carbon atoms, similar to the structure first illustrated by Thiele.

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answers: Benzene

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answers: Benzene

text: Cyclopropene is an organic compound with the formula . It is the simplest cycloalkene. It has a triangular structure. Because the ring is highly strained, cyclopropene is difficult to prepare, and a useful core for studies of bonding and molecular orbitals. The reduced length of the double bond compared to a single bond causes the angle opposite the double bond to narrow to about 51° from the 60° angle found in cyclopropane. As with cyclopropane, the carbon–carbon bonding in the ring has increased p character: the alkene carbons use sp hybridization for the ring.

text: Cyclopropene is an

text: organic compound

text: with the

text: formula

text: . It is the simplest

text: cycloalkene

text: . It has a

text: triangular

text: structure. Because the ring is highly

text: strained

text: , cyclopropene is difficult to prepare, and a useful core for studies of bonding and molecular orbitals. The reduced length of the

text: double bond

text: compared to a

text: single bond

text: causes the angle opposite the double bond to narrow to about 51° from the 60° angle found in

text: cyclopropane

text: . As with cyclopropane, the carbon–carbon bonding in the ring has increased

text: p character

text: : the alkene carbons use sp

text: hybridization

text: for the ring.

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answers: carbon–carbon bonding

text: Polyenes are poly-unsaturated organic compounds that contain at least three alternating double and single carbon–carbon bonds. These carbon–carbon double bonds interact in a process known as conjugation.  Related to polyenes are dienes, where there are only two alternating double and single bonds.  Other related class of compounds have three or more double bonds, but they are not alternating with single bonds.

text: Polyenes are poly-

text: unsaturated

text: organic compound

text: s that contain at least three alternating double and single

text: carbon

text: –carbon bonds. These carbon–carbon double bonds interact in a process known as

text: conjugation

text: .  Related to polyenes are

text: dienes

text: , where there are only two alternating double and single bonds.  Other related class of compounds have three or more double bonds, but they are not alternating with single bonds.

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answers: Polyenes

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answers: single

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answers: carbon–carbon

text: The compound's most noteworthy structural feature is the long carbon-carbon bond of 1.54 Å, which indicates the absence of pi-bonding between the two carbonyl centers.  The PhCO centers are planar, but the pair of benzoyl groups are twisted with respect to the other with a dihedral angle of 117°.  In less hindered analogues (glyoxal, biacetyl, oxalic acid derivatives), the (RCO) group adopts a planar, anti-conformation.

text: The compound's most noteworthy structural feature is the long

text: carbon-carbon bond

text: of 1.54

text: Å

text: , which indicates the absence of pi-bonding between the two carbonyl centers.  The PhCO centers are planar, but the pair of benzoyl groups are twisted with respect to the other with a

text: dihedral angle

text: of 117°.  In less

text: hindered

text: analogues (

text: glyoxal

text: biacetyl

text: oxalic acid

text: derivatives), the (RCO) group adopts a planar, anti-conformation.

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text: To provide further evidence on the mechanism of the dienone in which there is bonding between the two double bonds,the case of 4,4-diphenylcyclohexenone is presented here. It is seen that the rearrangement is quite different; thus two double bonds are required for a type A rearrangement. With one double bond one of the phenyl groups, originally at C-4, has migrated to C-3 (i.e. the beta carbon).

text: To provide further evidence on the mechanism of the dienone in which there is bonding between the two double bonds,the case of 4,4-diphenylcyclohexenone is presented here. It is seen that the rearrangement is quite different; thus two double bonds are required for a type A rearrangement. With one double bond one of the phenyl groups, originally at C-4, has migrated to C-3 (i.e. the beta carbon).

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answers: Carbon can form more compounds than any other element.

text: While carbon is understood to exclusively form four bonds, an interesting compound containing an octahedral hexacoordinated carbon atom has been reported. The cation of the compound is [(PhPAu)C]. This phenomenon has been attributed to the aurophilicity of the gold ligands.

text: While carbon is understood to exclusively form four bonds, an interesting compound containing an octahedral hexacoordinated carbon atom has been reported. The cation of the compound is [(PhPAu)C]. This phenomenon has been attributed to the

text: aurophilicity

text: of the gold ligands.

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answers: carbon is understood to exclusively form four bonds

text: Computer simulation suggests that these bonds are very polar with the negative charges residing on carbon.

text: Computer simulation suggests that these bonds are very polar with the negative charges residing on carbon.

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answers: polar

text: Carbon can form very long chains of interconnecting C-C bonds, a property that is called catenation. Carbon-carbon bonds are strong and stable. Through catenation, carbon forms a countless number of compounds.  A tally of unique compounds shows that more contain carbon that those that do not.  A similar claim can be made for hydrogen because most organic compounds also contain hydrogen.

text: Carbon can form very long chains of interconnecting C-C bonds, a property that is called

text: catenation

text: . Carbon-carbon bonds are strong and stable. Through catenation, carbon forms a countless number of compounds.  A tally of unique compounds shows that more contain carbon that those that do not.  A similar claim can be made for hydrogen because most organic compounds also contain hydrogen.

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answers: A tally of unique compounds

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answers: carbon forms a countless number of compounds

text: In an alkane, each carbon atom has 4 bonds (either C-C or C-H), and each hydrogen atom is joined to one of the carbon atoms (so in a C-H bond). The longest series of linked carbon atoms in a molecule is known as its carbon skeleton or carbon backbone. The number of carbon atoms may be thought of as the size of the alkane.

text: In an alkane, each carbon atom has 4 bonds (either C-C or

text: C-H

text: ), and each hydrogen atom is joined to one of the carbon atoms (so in a C-H bond). The longest series of linked carbon atoms in a molecule is known as its

text: carbon skeleton

text: or carbon backbone. The number of carbon atoms may be thought of as the size of the alkane.

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answers: each carbon atom has 4 bonds

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answers: C-H

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answers: alkane

text: In the above process, the oxygen atom in effect "steals" an electron bonding pair from the central carbon, forming the carbonyl group and simultaneously disrupting the bonds of the target carbon atom with one or more of its neighbours. The result is a cascading effect in which a single atomic oxygen reaction initiates significant "unraveling" of the local bonding structure, which in turn allows a wide range of aqueous reactions to affect previously impervious carbon atoms. Further oxidation, for example, can convert the initial carbonyl group into carbon dioxide and create a new carbonyl group on the neighbouring carbon whose bonds were disrupted:

text: In the above process, the oxygen atom in effect "steals" an electron bonding pair from the central carbon, forming the carbonyl group and simultaneously disrupting the bonds of the target carbon atom with one or more of its neighbours. The result is a cascading effect in which a single atomic oxygen reaction initiates significant "unraveling" of the local bonding structure, which in turn allows a wide range of aqueous reactions to affect previously impervious carbon atoms. Further oxidation, for example, can convert the initial carbonyl group into carbon dioxide and create a new carbonyl group on the neighbouring carbon whose bonds were disrupted:

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answers: carbon

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answers: carbonyl group

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answers: electron bonding pair

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answers: The result is a cascading effect

text: The properties of amorphous carbon films vary depending on the parameters used during deposition. The primary method for characterizing amorphous carbon is through the ratio of sp to sp hybridized bonds present in the material. Graphite consists purely of sp hybridized bonds, whereas diamond consists purely of sp hybridized bonds. Materials that are high in sp hybridized bonds are referred to as tetrahedral amorphous carbon, owing to the tetrahedral shape formed by sp hybridized bonds, or as diamond-like carbon (owing to the similarity of many physical properties to those of diamond).

text: The properties of amorphous carbon films vary depending on the parameters used during deposition. The primary method for characterizing amorphous carbon is through the ratio of sp to sp

text: hybridized bonds

text: present in the material. Graphite consists purely of sp hybridized bonds, whereas diamond consists purely of sp hybridized bonds. Materials that are high in sp hybridized bonds are referred to as tetrahedral amorphous carbon, owing to the tetrahedral shape formed by sp hybridized bonds, or as diamond-like carbon (owing to the similarity of many physical properties to those of diamond).

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text: A fat is made of two kinds of smaller molecules: monoglyceride and fatty acids. Fats are made of long chains of carbon (C) atoms. Some carbon atoms are linked by single bonds (-C-C-) and others are linked by double bonds (-C=C-). Double bonds can react with hydrogen to form single bonds. They are called saturated, because the second bond is broken up and each half of the bond is attached to (saturated with) a hydrogen atom. Most animal fats are saturated. The fats of plants and fish are generally unsaturated. Saturated fats tend to have higher melting points than their corresponding unsaturated fats, leading to the popular understanding that saturated fats tend to be solids at body temperatures, while unsaturated fats tend to be liquid oils.

text: A fat is made of two kinds of smaller molecules:

text: monoglyceride

text: and

text: fatty acids

text: . Fats are made of long chains of carbon (C) atoms. Some carbon atoms are linked by single bonds (-C-C-) and others are linked by

text: double bond

text: s (-C=C-). Double bonds can react with hydrogen to form single bonds. They are called

text: saturated

text: , because the second bond is broken up and each half of the bond is attached to (saturated with) a hydrogen atom. Most animal fats are saturated. The fats of plants and fish are generally unsaturated. Saturated fats tend to have higher

text: melting point

text: s than their corresponding unsaturated fats, leading to the popular understanding that saturated fats tend to be solids at body temperatures, while unsaturated fats tend to be liquid oils.

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answers: Most animal fats are saturated

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text: Benzotriyne or cyclo[6]carbon is a hypothetical chemical compound, an allotrope of carbon with molecular formula C.  The molecule is a ring of six carbon atoms, connected  either by alternating triple and single bonds or by double bonds.  It is, therefore, a potential member of the cyclo[n]carbon family.

text: Benzotriyne or cyclo[6]carbon is a hypothetical

text: chemical compound

text: , an

text: allotrope

text: of

text: carbon

text: with

text: molecular formula

text: C.  The molecule is a ring of six carbon atoms, connected  either by alternating triple and single bonds or by double bonds.  It is, therefore, a potential member of the

text: cyclo[n]carbon

text: family.

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text: The valence electrons can be counted using a Lewis electron dot diagram as  shown at the right for carbon dioxide. The electrons shared by the two atoms in a covalent bond are counted twice, once for each atom. In carbon dioxide each oxygen shares four electrons with the central carbon, two (shown in red) from the oxygen itself and two (shown in black) from the carbon. All four of these electrons are counted in both the carbon octet and the oxygen octet.

text: The valence electrons can be counted using a

text: Lewis electron dot diagram

text: as  shown at the right for carbon dioxide. The electrons shared by the two atoms in a

text: covalent bond

text: are counted twice, once for each atom. In carbon dioxide each oxygen shares four electrons with the central carbon, two (shown in red) from the oxygen itself and two (shown in black) from the carbon. All four of these electrons are counted in both the carbon octet and the oxygen octet.

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answers: carbon

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answers: two

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answers: Hydrocarbon

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answers: carbon dioxide

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answers: each oxygen shares four electrons

answers: NDQ_016401

answers: It is impossible to say

text: In the first step, three Mgstabilize the anionic leaving group, pyrophosphate, on dimethylallyl pyrophosphate (DMAPP). The loss of pyrophosphate forms an allylic carbocation on dimethylallyl. In the second step, the reactive C3-C5 double bond in isopentyl pyrophosphate (IPP) nucleophilically attacks the previously formed dimethylallyl carbocation in a 5-carbon/5-carbon condensation reaction. The final step involves pyrophosphate held in the trinuclear Mg center acting as a catalytic base in an elimination reaction to form geranyl pyrophosphate. A second consecutive round of geranyl pyrophosphate ionization, condensation with IPP, and elimination forms farnesyl pyrophosphate.

text: In the first step, three Mgstabilize the anionic leaving group, pyrophosphate, on

text: dimethylallyl pyrophosphate

text: (DMAPP). The loss of pyrophosphate forms an allylic carbocation on dimethylallyl. In the second step, the reactive C3-C5 double bond in isopentyl pyrophosphate (IPP) nucleophilically attacks the previously formed dimethylallyl carbocation in a 5-carbon/5-carbon condensation reaction. The final step involves pyrophosphate held in the trinuclear Mg center acting as a catalytic base in an elimination reaction to form geranyl pyrophosphate. A second consecutive round of geranyl pyrophosphate ionization, condensation with IPP, and elimination forms farnesyl pyrophosphate.

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answers: carbon

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answers: 5-carbon

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answers: isopentyl

answers: NDQ_016400

answers: 5

answers: NDQ_016401

answers: carbon

text: Two families of dioxygenases were discovered by Osamu Hayaishi and Kizo Hashimoto in 1950: catechol 1,2-dioxygenase and catechol 2,3-dioxygenase (2,3-CTD). The two enzymes were identified to be a part of two separate catechol dioxygenase families: 1,2-CTD was classified as an intradiol dioxygenase while 2,3-CTD was classified as an extradiol dioxygenase. The two enzymes can be distinguished based on their reaction products and cofactors. 1,2-CTD uses Fe as a cofactor to cleave the carbon-carbon bond between the phenolic hydroxyl groups of catechol, thus yielding muconic acid as its product. In contrast, 2,3-CTD utilizes Fe as a cofactor to cleave the carbon-carbon bond adjacent to the phenolic hydroxyl groups of catechol, thus yielding 2-hydroxymuconaldehye as its product.

text: Two families of dioxygenases were discovered by Osamu Hayaishi and Kizo Hashimoto in 1950: catechol 1,2-dioxygenase and

text: catechol 2,3-dioxygenase

text: (2,3-CTD). The two enzymes were identified to be a part of two separate catechol dioxygenase families: 1,2-CTD was classified as an intradiol dioxygenase while 2,3-CTD was classified as an

text: extradiol dioxygenase

text: . The two enzymes can be distinguished based on their reaction products and cofactors. 1,2-CTD uses Fe as a cofactor to cleave the carbon-carbon bond between the phenolic hydroxyl groups of catechol, thus yielding muconic acid as its product. In contrast, 2,3-CTD utilizes Fe as a cofactor to cleave the carbon-carbon bond adjacent to the phenolic hydroxyl groups of catechol, thus yielding 2-hydroxymuconaldehye as its product.

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answers: NDQ_016401

answers: Muconic acid

text: For example, in the image below, the skeletal formula of hexane is shown. The carbon atom labeled C appears to have only one bond, so there must also be three hydrogens bonded to it, in order to make its total number of bonds four.  The carbon atom labelled C has two bonds to other carbons and is therefore bonded to two hydrogen atoms as well. A ball-and-stick model of the actual molecular structure of hexane, as determined by X-ray crystallography, is shown for comparison, in which carbon atoms are depicted as black balls and hydrogen atoms as white ones.

text: For example, in the image below, the skeletal formula of

text: hexane

text: is shown. The carbon atom labeled C appears to have only one bond, so there must also be three hydrogens bonded to it, in order to make its total number of bonds four.  The carbon atom labelled C has two bonds to other carbons and is therefore bonded to two hydrogen atoms as well. A

text: ball-and-stick model

text: of the actual molecular structure of hexane, as determined by

text: X-ray crystallography

text: , is shown for comparison, in which carbon atoms are depicted as black balls and hydrogen atoms as white ones.

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answers: Hexane

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answers: hexane

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answers: hexane

text: Dry ice is the solid form of carbon dioxide (CO), a molecule consisting of a single carbon atom bonded to two oxygen atoms. Dry ice is colorless, non-flammable, with a sour zesty odor, and can lower the pH of a solution when dissolved in water, forming carbonic acid (HCO).

text: Dry ice is the solid form of

text: carbon dioxide

text: (CO), a molecule consisting of a single

text: carbon

text: atom

text: bonded

text: to two

text: oxygen

text: atom

text: s. Dry ice is colorless, non-flammable, with a sour zesty odor, and can lower the

text: pH

text: of a solution when dissolved in water, forming

text: carbonic acid

text: (HCO).

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answers: (CO)

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answers: two oxygen atoms

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answers: Dry ice

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text: In these compounds, it is not possible for the carbon atoms to assume the 109.5° bond angles with standard sp hybridization. Increasing the p-character to sp (i.e.  s-density and  p-density) makes it possible to reduce the bond angles to 60°. At the same time, the carbon-to-hydrogen bonds gain more s-character, which shortens them. In cyclopropane, the maximum electron density between two carbon atoms does not correspond to the internuclear axis, hence the name bent bond. In cyclopropane, the interorbital angle is 104°. This bending can be observed experimentally by X-ray diffraction of certain cyclopropane derivatives: the deformation density is outside the line of centers between carbons. The carbon–carbon bond lengths are shorter than in a regular alkane bond: 151 pm versus 153 pm.

text: In these compounds, it is not possible for the carbon atoms to assume the 109.5°

text: bond angle

text: s with standard sp hybridization. Increasing the p-character to sp (i.e.  s-density and  p-density) makes it possible to reduce the bond angles to 60°. At the same time, the carbon-to-hydrogen bonds gain more s-character, which shortens them. In cyclopropane, the maximum electron density between two carbon atoms does not correspond to the internuclear axis, hence the name bent bond. In cyclopropane, the interorbital angle is 104°. This bending can be observed experimentally by

text: X-ray diffraction

text: of certain cyclopropane derivatives: the

text: deformation density

text: is outside the line of centers between carbons. The carbon–carbon

text: bond length

text: s are shorter than in a regular alkane bond: 151

text: pm

text: versus 153 pm.

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answers: NDQ_016401

answers: cyclopropane

text: In valence bond theory, two atoms each contribute an atomic orbital and the electrons in the orbital overlap form a covalent bond. Atoms do not usually contribute a pure hydrogen-like orbital to bonds. If atoms could only contribute hydrogen-like orbitals, then the experimentally confirmed tetrahedral structure of methane would not be possible as the 2s and 2p orbitals of carbon do not have that geometry. That and other contradictions led to the proposing of orbital hybridisation. In that framework, atomic orbitals are allowed to mix to produce an equivalent number of orbitals of differing shapes and energies. In the aforementioned case of methane, the 2s and three 2p orbitals of carbon are hybridized to yield four equivalent sp orbitals, which resolves the structure discrepancy. Orbital hybridisation allowed valence bond theory to successfully explain the geometry and properties of a vast number of molecules.

text: In valence bond theory, two atoms each contribute an atomic orbital and the electrons in the orbital overlap form a covalent bond. Atoms do not usually contribute a pure

text: hydrogen-like orbital

text: to bonds. If atoms could only contribute hydrogen-like orbitals, then the experimentally confirmed tetrahedral structure of

text: methane

text: would not be possible as the 2s and 2p orbitals of carbon do not have that geometry. That and other contradictions led to the proposing of

text: orbital hybridisation

text: . In that framework, atomic orbitals are allowed to mix to produce an equivalent number of orbitals of differing shapes and energies. In the aforementioned case of methane, the 2s and three 2p orbitals of carbon are hybridized to yield four equivalent sp orbitals, which resolves the structure discrepancy. Orbital hybridisation allowed valence bond theory to successfully explain the geometry and properties of a vast number of molecules.

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answers: vast number of molecules

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answers: Orbital hybridisation

text: A carbon–oxygen bond is a covalent bond between carbon and oxygen.    Oxygen has 6 valence electrons and prefers to either share two electrons in bonding with carbon, leaving the 4 nonbonding electrons in 2 lone pairs :O:   or to share two pairs of electrons to form the carbonyl functional group. =O: Simple representatives of these two bond types are the OH in alcohols such as the ethanol in beverages and fuels and the C=O in ketones  (as well as many other related carbonyl compounds).

text: A carbon–oxygen bond is a

text: covalent bond

text: between

text: carbon

text: and

text: oxygen

text: .    Oxygen has 6

text: valence electron

text: s and prefers to either share two electrons in bonding with carbon, leaving the 4 nonbonding electrons in 2

text: lone pair

text: s :O:   or to share two pairs of electrons to form the

text: carbonyl functional group

text: . =O: Simple representatives of these two bond types are the OH in

text: alcohol

text: s such as the ethanol in beverages and fuels and the C=O in

text: ketone

text: s  (as well as many other related

text: carbonyl compound

text: s).

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text: Inorganic compounds can be defined as any compound that is not organic compound. Some simple compounds which contain carbon are usually considered inorganic. These include carbon monoxide, carbon dioxide, carbonates, cyanides, cyanates, carbides, and thiocyanates. In contrast, methane and formic acid are generally considered to be simple examples of organic compounds, although the Inorganic Crystal Structure Database (ICSD), in its definition of "inorganic" carbon compounds, states that such compounds may contain either C-H or C-C bonds, but not both.

text: Inorganic compounds can be defined as any compound that is not

text: organic compound

text: . Some simple compounds which contain carbon are usually considered inorganic. These include

text: carbon monoxide

text: carbon dioxide

text: carbonate

text: s,

text: cyanide

text: s,

text: cyanate

text: s,

text: carbide

text: s, and

text: thiocyanate

text: s. In contrast,

text: methane

text: and

text: formic acid

text: are generally considered to be simple examples of

text: organic compound

text: s, although the Inorganic Crystal Structure Database (ICSD), in its definition of "inorganic" carbon compounds, states that such compounds may contain either C-H or C-C bonds, but not both.

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answers: Inorganic

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answers: thiocyanates

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answers: Inorganic

text: The modest acidity of carbons adjacent to the sulfonyl group has made sulfones useful for organic synthesis. Upon removal of the sulfonyl group with desulfonylation or reductive elimination, the net result is the formation of a carbon-carbon bond single or double bond between two unfunctionalized carbons, a ubiquitous motif in synthetic targets. In a synthesis of (–)-anthoplalone, Julia olefination was used to establish the (E)-alkene in the target.

text: The modest acidity of carbons adjacent to the sulfonyl group has made sulfones useful for organic synthesis. Upon removal of the sulfonyl group with desulfonylation or reductive elimination, the net result is the formation of a carbon-carbon bond single or double bond between two unfunctionalized carbons, a ubiquitous motif in synthetic targets. In a synthesis of (–)-anthoplalone, Julia olefination was used to establish the (E)-alkene in the target.

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answers: ubiquitous motif

answers: NDQ_016396

answers: single or double bond

answers: NDQ_016398

answers: hydrocarbon

answers: NDQ_016399

answers: (–)-anthoplalone

answers: NDQ_016400

answers: two

answers: NDQ_016401

answers: ubiquitous motif

text: Ullman used Goldeberg design synthesis to develop copper based reactions that enabled the formation of C-C, C-N and C-S bonds. Ullmann chemistry is based on the formation of a carbon-carbon bond via condensation of aryl halides in the presence of a copper compound. This type of reaction has been useful for ring closures, aryl bond formation, synthesis of symmetrical and unsymmetrical biaryl compounds, synthesis of oligophenylenes and so on.

text: Ullman

text: used Goldeberg design

text: synthesis

text: to develop copper based reactions that enabled the formation of C-C, C-N and C-S bonds. Ullmann chemistry is based on the formation of a carbon-carbon bond via condensation of aryl halides in the presence of a copper compound. This type of reaction has been useful for ring closures, aryl bond formation, synthesis of symmetrical and unsymmetrical biaryl compounds, synthesis of oligophenylenes and so on.

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text: Carbon dioxide molecule: Each carbon atom has four electrons in its outermost shell and each oxygen atom has six electrons in its outermost shell. Thus, each carbon atom requires four, and each oxygen atom requires two more electrons to acquire noble gas configurations. To achieve this, two oxygen atoms form a double covalent bond with carbon.

text: Carbon dioxide

text: molecule: Each carbon atom has four electrons in its outermost shell and each

text: oxygen

text: atom has six electrons in its outermost shell. Thus, each carbon atom requires four, and each oxygen atom requires two more electrons to acquire noble gas configurations. To achieve this, two oxygen atoms form a double covalent bond with carbon.

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text: The inductive effect can be explained with Bent’s rule. The inductive effect is the transmission of charge through covalent bonds and Bent’s rule provides a mechanism for such results via differences in hybridisation. In the table below, as the groups bonded to the central carbon become more electronegative, the central carbon becomes more electron-withdrawing as measured by the polar substituent constant. The polar substituent constants are similar in principle to σ values from the Hammett equation, as an increasing value corresponds to a greater electron-withdrawing ability. Bent's rule suggests that as the electronegativity of the groups increase, more p character is diverted towards those groups, which leaves more s character in the bond between the central carbon and the R group. As s orbitals have greater electron density closer to the nucleus than p orbitals, the electron density in the C−R bond will more shift towards the carbon as the s character increases. This will make the central carbon more electron-withdrawing to the R group. Thus, the electron-withdrawing ability of the substituents has been transferred to the adjacent carbon, exactly what the inductive effect predicts.

text: The

text: inductive effect

text: can be explained with Bent’s rule. The inductive effect is the transmission of charge through covalent bonds and Bent’s rule provides a mechanism for such results via differences in hybridisation. In the table below, as the groups bonded to the central carbon become more electronegative, the central carbon becomes more electron-withdrawing as measured by the

entity_section: Polar Substituent Constants.2C .CF.83.2A

text: polar substituent constant

text: . The polar substituent constants are similar in principle to σ values from the

text: Hammett equation

text: , as an increasing value corresponds to a greater electron-withdrawing ability. Bent's rule suggests that as the electronegativity of the groups increase, more p character is diverted towards those groups, which leaves more s character in the bond between the central carbon and the R group. As s orbitals have greater electron density closer to the nucleus than p orbitals, the electron density in the C−R bond will more shift towards the carbon as the s character increases. This will make the central carbon more electron-withdrawing to the R group. Thus, the electron-withdrawing ability of the substituents has been transferred to the adjacent carbon, exactly what the inductive effect predicts.

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text: When the first bromine atom attacks the carbon–carbon π-bond, it leaves behind one of its electrons with the other bromine that it was bonded to in Br. That other atom is now a negative bromide anion and is attracted to the slight positive charge on the carbon atoms. It is blocked from nucleophilic attack on one side of the carbon chain by the first bromine atom and can only attack from the other side. As it attacks and forms a bond with one of the carbons, the bond between the first bromine atom and the other carbon atoms breaks, leaving each carbon atom with a halogen substituent.

text: When the first bromine atom attacks the carbon–carbon

text: π-bond

text: , it leaves behind one of its electrons with the other bromine that it was bonded to in Br. That other atom is now a negative

text: bromide

text: anion and is attracted to the slight positive charge on the carbon atoms. It is blocked from

text: nucleophilic attack

text: on one side of the carbon chain by the first bromine atom and can only attack from the other side. As it attacks and forms a bond with one of the carbons, the bond between the first bromine atom and the other carbon atoms breaks, leaving each carbon atom with a halogen substituent.

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text: Hyperconjugation, which describes the stabilizing interaction between the HOMO of the alkyl group and the LUMO of the double bond, also helps explain the influence of alkyl substitutions on the stability of alkenes. In regards to orbital hybridization, a bond between an sp carbon and an sp carbon is stronger than a bond between two sp-hybridized carbons. Computations reveal a dominant stabilizing hyperconjugation effect of 6 kcal/mol per alkyl group.

text: Hyperconjugation

text: , which describes the stabilizing interaction between the

text: HOMO

text: of the alkyl group and the

text: LUMO

text: of the double bond, also helps explain the influence of alkyl substitutions on the stability of alkenes. In regards to

text: orbital hybridization

text: , a bond between an

text: sp

text: carbon and an

text: sp

text: carbon is stronger than a bond between two sp-hybridized carbons. Computations reveal a dominant stabilizing hyperconjugation effect of 6 kcal/mol per alkyl group.

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answers: alkenes

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answers: Alkyl

text: As is standard for resonance diagrams, the use of a double-headed arrow indicates that two structures are not distinct entities but merely hypothetical possibilities. Neither is an accurate representation of the actual compound, which is best represented by a hybrid (average) of these structures, as can be seen at right.  A C=C bond is shorter than a C−C bond, but benzene is perfectly hexagonal—all six carbon–carbon bonds have the same length, intermediate between that of a single and that of a double bond.

text: As is standard for resonance diagrams, the use of a double-headed arrow indicates that two structures are not distinct entities but merely hypothetical possibilities. Neither is an accurate representation of the actual compound, which is best represented by a hybrid (average) of these structures, as can be seen at right.  A C=C bond is shorter than a C−C bond, but benzene is perfectly hexagonal—all six carbon–carbon bonds have the same

text: length

text: , intermediate between that of a

text: single

text: and that of a

text: double bond

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answers: Benzene

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answers: carbon–carbon bonds have the same length

text: The ability of carbon to form four bonds also means it can exist in a huge variety of chemical structures, such as long chains and even rings, making it a rarity amongst the elements. This helped to explain the abundance of carbon in all life forms, from protein and fat, to DNA and cellulose, and why carbon exists in more compounds than any other element.

text: The ability of carbon to form four bonds also means it can exist in a huge variety of chemical structures, such as long chains and even rings, making it a rarity amongst the elements. This helped to explain the abundance of carbon in all life forms, from protein and fat, to DNA and cellulose, and why carbon exists in more compounds than any other element.

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answers: more compounds than any other element

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answers: cellulose

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answers: carbon exists in more compounds than any other element

text: one carbon–oxygen–phosphorus bondings, no phosphorus–oxygen double bonds but two phosphorus–carbon bonds in phosphinites.

text: one carbon–oxygen–phosphorus bondings, no phosphorus–oxygen double bonds but two phosphorus–carbon bonds in phosphinites.

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text: He first proposed the idea of possible tetrahedral arrangement of valence bonds in carbon compounds in 1862.

text: He first proposed the idea of possible tetrahedral arrangement of valence bonds in carbon compounds in 1862.

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answers: carbon compounds

text: Following the same rules, the carboxylic acid carbon atom gets the other one valence electron from the C−C bond. None of its other valence electrons are counted here because they are involved in bonding to oxygen atoms, which are more electronegative than carbon. For a carbon with one electron, the oxidation state is +3, again calculated against its neutral four-electron count. The oxygen atoms each have an oxidation state of −2; they get 8 electrons each (4 from the lone pairs and 4 from the bonds), while a neutral oxygen atom would have 6. The hydrogen atoms each have oxidation state +1, because they surrender their electron to the more electronegative atoms to which they are bonded.

text: Following the same rules, the

text: carboxylic acid

text: carbon atom gets the other one valence electron from the C−C bond. None of its other valence electrons are counted here because they are involved in bonding to oxygen atoms, which are more electronegative than carbon. For a carbon with one electron, the oxidation state is +3, again calculated against its neutral four-electron count. The oxygen atoms each have an oxidation state of −2; they get 8 electrons each (4 from the lone pairs and 4 from the bonds), while a neutral oxygen atom would have 6. The hydrogen atoms each have oxidation state +1, because they surrender their electron to the more electronegative atoms to which they are bonded.

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answers: It can form more compounds than any other element.

text: The carbon atom can use its two singly occupied p-type orbitals, to form two covalent bonds with two hydrogen atoms, yielding the singlet methylene CH, the simplest carbene. The carbon atom can also bond to four hydrogen atoms by an excitation of an electron from the doubly occupied 2s orbital to the empty 2p orbital, producing four singly occupied orbitals.

text: The carbon atom can use its two singly occupied p-type orbitals, to form two

text: covalent bond

text: s with two hydrogen atoms, yielding the singlet

text: methylene

text: CH, the simplest

text: carbene

text: . The carbon atom can also bond to four hydrogen atoms by an excitation of an electron from the doubly occupied 2s orbital to the empty 2p orbital, producing four singly occupied orbitals.

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answers: It can use its two singly occupied p-type orbitals

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answers: Hydrocarbon

answers: NDQ_016399

answers: methylene

answers: NDQ_016400

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answers: carbon atom can use its two singly occupied p-type orbitals

text: The degradation of serine to pyruvate is an example of a pyridoxal phosphate-dependent (PLP) catalyzed Beta-elimination reaction. Beta-eliminations mediated by PLP yields products that have undergone a two-electron oxidation at C-alpha.  In general, beta-eliminations involve the removal of a halide and a proton from the adjacent beta-carbon to give a double bond; thus, the origin of the double bond pi electrons are from the C-H bond on the beta carbon of the substrate.

text: The degradation of

text: serine

text: to

text: pyruvate

text: is an example of a

text: pyridoxal phosphate-dependent (PLP)

text: catalyzed Beta-

text: elimination

text: reaction. Beta-eliminations mediated by PLP yields products that have undergone a two-electron

text: oxidation

text: at C-alpha.  In general, beta-eliminations involve the removal of a

text: halide

text: and a proton from the adjacent

text: beta-carbon

text: to give a

text: double bond

text: ; thus, the origin of the double bond

text: pi electrons

text: are from the C-H bond on the beta carbon of the substrate.

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answers: beta-carbon

text: Organoiridium compounds contain iridium-carbon chemical bonds. As a third row transition metal, iridium forms very stable bonds to carbon and the organometallic chemistry is extensive.

text: Organoiridium compounds contain

text: iridium

text: carbon

text: chemical bond

text: s. As a third row transition metal, iridium forms very stable bonds to carbon and the organometallic chemistry is extensive.

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answers: Organoiridium compounds

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answers: very stable bonds

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answers: hydrocarbon

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answers: Organoiridium

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answers: Organoiridium compounds

text: In coupling reactions a metal catalyses a coupling between two formal radical fragments. Common coupling reactions with arenes result in the formation of new carbon–carbon bonds e.g., alkylarenes, vinyl arenes, biraryls, new carbon–nitrogen bonds (anilines) or new carbon–oxygen bonds (aryloxy compounds). An example is the direct arylation of perfluorobenzenes

text: In

text: coupling reaction

text: s a metal catalyses a coupling between two formal radical fragments. Common coupling reactions with arenes result in the formation of new

text: carbon–carbon bond

text: s e.g., alkylarenes, vinyl arenes, biraryls, new

text: carbon–nitrogen bond

text: s (anilines) or new

text: carbon–oxygen bond

text: s (aryloxy compounds). An example is the direct arylation of

text: perfluorobenzenes

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answers: carbon–carbon bonds

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answers: carbon–carbon bonds

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answers: Alkylarenes

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answers: aryloxy compounds

answers: NDQ_016400

answers: carbon–oxygen

answers: NDQ_016401

answers: carbon–carbon bonds

text: A cyclo[n]carbon is a chemical compound consisting solely of an n number of carbon atoms linked in a ring by double covalent bonds (a cyclic cumulene).  Since the compound is composed only of carbon atoms, it is considered an exotic carbon allotrope.  If n is even there is an alternative structure where the bonds alternate between single and triple bonds (a cyclic polyyne).  The (hypothetical) six-carbon member of this family (C) is also called benzotriyne.

text: A cyclo[n]carbon is a

text: chemical compound

text: consisting solely of an n number of carbon atoms linked in a ring by

text: double covalent bond

text: s (a cyclic

text: cumulene

text: ).  Since the compound is composed only of carbon atoms, it is considered an exotic carbon

text: allotrope

text: .  If n is even there is an alternative structure where the bonds alternate between single and triple bonds (a cyclic

text: polyyne

text: ).  The (hypothetical) six-carbon member of this family (C) is also called

text: benzotriyne

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answers: alternate between single and triple bonds

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answers: cyclo[n]carbon

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answers: double

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answers: cyclic cumulene

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answers: cyclic polyyne

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answers: It is considered an exotic carbon allotrope

text: Comparing the two contributing structures of benzene, all single and double bonds are interchanged. Bond lengths can be measured, for example using X-ray diffraction. The average length of a C–C single bond is 154 pm; that of a C=C double bond is 133 pm. In localized cyclohexatriene, the carbon–carbon bonds should be alternating 154 and 133 pm. Instead, all carbon–carbon bonds in benzene are found to be about 139 pm, a bond length intermediate between single and double bond. This mixed single and double bond (or triple bond) character is typical for all molecules in which bonds have a different bond order in different contributing structures. Bond lengths can be compared using bond orders. For example, in cyclohexane the bond order is 1 while that in benzene is 1 + (3 ÷ 6) = . Consequently, benzene has more double bond character and hence has a shorter bond length than cyclohexane.

text: Comparing the two contributing structures of

text: benzene

text: , all single and double bonds are interchanged.

text: Bond length

text: s can be measured, for example using

text: X-ray diffraction

text: . The average length of a C–C single bond is 154

text: pm

text: ; that of a C=C double bond is 133 pm. In localized cyclohexatriene, the carbon–carbon bonds should be alternating 154 and 133 pm. Instead, all carbon–carbon bonds in benzene are found to be about 139 pm, a bond length intermediate between single and double bond. This mixed single and double bond (or triple bond) character is typical for all molecules in which bonds have a different

text: bond order

text: in different contributing structures. Bond lengths can be compared using bond orders. For example, in cyclohexane the bond order is 1 while that in benzene is 1 + (3 ÷ 6) = . Consequently, benzene has more double bond character and hence has a shorter bond length than cyclohexane.

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answers: This mixed single and double bond

answers: NDQ_016396

answers: C–C single bond

answers: NDQ_016398

answers: benzene

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answers: cyclohexatriene

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answers: 139 pm

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answers: carbon–carbon bonds

text: Two charge states of this defect, neutral N-V and negative N-V, are known from spectroscopic studies using optical absorption, photoluminescence (PL), electron paramagnetic resonance (EPR) and optically detected magnetic resonance (ODMR), which can be viewed as a hybrid of PL and EPR; most details of the structure originate from EPR. A nitrogen atom has five valence electrons. Three of them covalently bond to the carbon atoms and two remain non-bonded and are called a lone pair. The vacancy has three unpaired electrons. Two of them make a quasi covalent bond and one remains unpaired. The overall symmetry, however, is axial (trigonal C); one can visualize this by imagining the three unpaired vacancy electrons continuously exchanging their roles.

text: Two charge states of this defect, neutral N-V and negative N-V, are known from

text: spectroscopic

text: studies using

text: optical absorption

text: photoluminescence

text: (PL),

text: electron paramagnetic resonance

text: (EPR) and optically detected magnetic resonance (ODMR), which can be viewed as a hybrid of PL and EPR; most details of the structure originate from EPR. A nitrogen atom has five valence electrons. Three of them

text: covalently

text: bond to the carbon atoms and two remain non-bonded and are called a

text: lone pair

text: . The vacancy has three unpaired electrons. Two of them make a quasi covalent bond and one remains unpaired. The overall symmetry, however, is axial (trigonal

text: C

text: ); one can visualize this by imagining the three unpaired vacancy electrons continuously exchanging their roles.

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answers: nitrogen atoms

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answers: Three

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answers: neutral N-V

answers: NDQ_016400

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answers: NDQ_016401

answers: A nitrogen atom has five valence electrons

text: The positions of the double bonds in a fatty acid chain can, therefore, be indicated in two ways, using the C-n or the ω-n notation. Thus, in an 18 carbon fatty acid, a double bond between C-12 (or ω-7) and C-13 (or ω-6) is reported either as Δ if counted from the –COOH end (indicating only the “beginning” of the double bond), or as ω-6 (or omega-6) if counting from the –CH end. The “Δ” is the Greek letter “delta”, which translates into “D” ( for Double bond) in the Roman alphabet. Omega (ω) is the last letter in the Greek alphabet, and is therefore used to indicate the “last” carbon atom in the fatty acid chain. Since the ω-n notation is used almost exclusively to indicate the positions of the double bonds close to the –CH end in essential fatty acids, there is no necessity for an equivalent “Δ”-like notation - the use of the “ω-n” notation always refers to the position of a double bond.

text: The positions of the double bonds in a fatty acid chain can, therefore, be indicated in two ways, using the C-n or the ω-n notation. Thus, in an 18 carbon fatty acid, a double bond between C-12 (or ω-7) and C-13 (or ω-6) is reported either as Δ if counted from the –COOH end (indicating only the “beginning” of the double bond), or as ω-6 (or omega-6) if counting from the –CH end. The “Δ” is the Greek letter “delta”, which translates into “D” ( for Double bond) in the Roman alphabet. Omega (ω) is the last letter in the Greek alphabet, and is therefore used to indicate the “last” carbon atom in the fatty acid chain. Since the ω-n notation is used almost exclusively to indicate the positions of the double bonds close to the –CH end in

text: essential fatty acid

text: s, there is no necessity for an equivalent “Δ”-like notation - the use of the “ω-n” notation always refers to the position of a double bond.

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answers: Omega

text: Carbene insertion utilize a different strategy for the functionalization of methane. A strategy using metallocarbenes has been shown with several linear and branched alkanes with rhodium, silver, copper, and gold-based catalysts. With a carbene ligand attached to a metal center, it can be transferred from the coordination sphere and inserted into an activated C-H bond. In this case, there is no interaction between the metal center and the alkane in question, which separates this method from the other methods mentioned above. The general mechanism for this cycle begins with the reaction of an electron-poor metal center with a diazocompound to form a metallo-carbene intermediate. In order for this reaction to occur, the diazocompound must be very electrophilic, since the C-H bond is such a poor nucleophile as well as being an unactivated alkane. The reaction then proceeds in a concerted manner, where the C-H bond of the incoming molecule coordinates with the carbene carbon of the metallocarbene complex. The hydrocarbon then dissociates from the metal center to regenerate the catalyst and free the newly formed carbon-carbon bond ().

text: Carbene insertion

text: utilize a different strategy for the functionalization of methane. A strategy using metallocarbenes has been shown with several linear and branched alkanes with

text: rhodium

text: silver

text: copper

text: , and

text: gold

text: -based catalysts. With a carbene ligand attached to a metal center, it can be transferred from the

text: coordination sphere

text: and inserted into an activated C-H bond. In this case, there is no interaction between the metal center and the alkane in question, which separates this method from the other methods mentioned above. The general mechanism for this cycle begins with the reaction of an electron-poor metal center with a diazocompound to form a metallo-carbene intermediate. In order for this reaction to occur, the diazocompound must be very electrophilic, since the C-H bond is such a poor nucleophile as well as being an unactivated alkane. The reaction then proceeds in a concerted manner, where the C-H bond of the incoming molecule coordinates with the carbene carbon of the metallocarbene complex. The hydrocarbon then dissociates from the metal center to regenerate the catalyst and free the newly formed carbon-carbon bond ().

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answers: Carbene carbon

text: The semipinacol rearrangement is a rearrangement reaction in organic chemistry involving a heterosubstituted alcohol of the type RR(HO)C–C(X)RR. The hetero substituent can be a halogen (Cl, Br, I), a tosylate, a mesylate or a thiol group. This reaction proceeds by removal of the leaving group X forming a carbocation as electron deficient center. One of the adjacent alkyl groups then migrates to the positive carbon in a 1,2-shift. Simultaneously with the shift, a pi bond forms from the oxygen to carbon, assisting in driving the migrating group off its position. The result is a ketone or aldehyde. In another definition all semipinacol rearrangements "share a common reactive species in which an electrophilic carbon center, including but not limited to carbocations, is vicinal to an oxygen-containing carbon and can drive the 1,2-migration of a C–C or C–H bond to terminate the process, generating a carbonyl group ".

text: The semipinacol rearrangement is a

text: rearrangement reaction

text: in

text: organic chemistry

text: involving a heterosubstituted alcohol of the type RR(HO)C–C(X)RR. The hetero substituent can be a

text: halogen

text: (Cl, Br, I), a

text: tosylate

text: , a

text: mesylate

text: or a

text: thiol

text: group. This reaction proceeds by removal of the

text: leaving group

text: X forming a

text: carbocation

text: as electron deficient center. One of the adjacent alkyl groups then migrates to the positive carbon in a

text: . Simultaneously with the shift, a

text: pi bond

text: forms from the oxygen to carbon, assisting in driving the migrating group off its position. The result is a

text: ketone

text: or

text: aldehyde

text: . In another definition all semipinacol rearrangements "share a common reactive species in which an electrophilic carbon center, including but not limited to carbocations, is vicinal to an oxygen-containing carbon and can drive the 1,2-migration of a C–C or C–H bond to terminate the process, generating a carbonyl group ".

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answers: carbon

text: A base is also defined as a molecule that has the ability to accept an electron pair bond by entering another atom's valence shell through its possession of one electron pair. There are a limited number of elements that have atoms with the ability to provide a molecule with basic properties. Carbon can act as a base as well as nitrogen and oxygen. Fluorine and sometimes rare gases possess this ability as well. This occurs typically in compounds such as butyl lithium, alkoxides, and metal amides such as sodium amide. Bases of carbon, nitrogen and oxygen without resonance stabilization are usually very strong, or superbases, which cannot exist in a water solution due to the acidity of water. Resonance stabilization, however, enables weaker bases such as carboxylates; for example, sodium acetate is a weak base.

text: A base is also defined as a molecule that has the ability to accept an electron pair bond by entering another atom's valence shell through its possession of one electron pair. There are a limited number of elements that have atoms with the ability to provide a molecule with basic properties.

text: Carbon

text: can act as a base as well as

text: nitrogen

text: and

text: oxygen

text: . Fluorine and sometimes rare gases possess this ability as well. This occurs typically in compounds such as

text: butyl lithium

text: alkoxide

text: s, and metal

text: amide

text: s such as

text: sodium amide

text: . Bases of carbon, nitrogen and oxygen without

text: resonance

text: stabilization are usually very strong, or

text: superbase

text: s, which cannot exist in a water solution due to the acidity of water. Resonance stabilization, however, enables weaker bases such as carboxylates; for example,

text: sodium acetate

text: is a

text: weak base

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answers: Carbon can act as a base

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text: In cycloalkanes, each carbon is bonded nonpolar covalently to two carbons and two hydrogen. The carbons have sp hybrization and should have ideal bond angles of 109.5°. Due to the limitations of cyclic structure, however, the ideal angle is only achieved in a six carbon ring — cyclohexane in chair conformation.  For other cycloalkanes, the bond angles deviate from ideal. In cyclopropanes (3 carbons) and cyclobutanes (4 carbons) the C-C bonds are 60° and ~90° respectively.

text: In cycloalkanes, each carbon is bonded

text: nonpolar

text: covalently

text: to two carbons and two hydrogen. The carbons have

text: sp hybrization

text: and should have ideal bond angles of 109.5°. Due to the limitations of cyclic structure, however, the ideal angle is only achieved in a six carbon ring —

text: cyclohexane

text: in

text: chair conformation

text: .  For other cycloalkanes, the bond angles deviate from ideal. In cyclopropanes (3 carbons) and cyclobutanes (4 carbons) the C-C bonds are 60° and ~90° respectively.

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text: The differences in the chiral angle and the diameter cause the differences in the properties of the various carbon nanotubes. For example, it can be shown that an (n,m) carbon nanotube is metallic when n = m, has a small gap (i.e. semi-metallic) when n – m = 3i, where i is an integer, and is semiconducting when n – m ≠ 3i. This is due to the fact that the periodic boundary conditions for the one-dimensional carbon nanotubes permit only a few wave vectors to exist around the circumference of carbon nanotubes. Metallic conduction occurs when one of these wave vectors passes through the K-point of graphene’s 2D hexagonal Brillouin zone, where the valence and conduction bands are degenerate. For the semiconducting carbon nanotubes, there is a diameter dependency on bandgap. For example, according to a single-particle tight-binding description of the electronic structure,

text: The differences in the chiral angle and the diameter cause the differences in the properties of the various carbon nanotubes. For example, it can be shown that an (n,m) carbon nanotube is metallic when n = m, has a small gap (i.e. semi-metallic) when n – m = 3i, where i is an integer, and is semiconducting when n – m ≠ 3i. This is due to the fact that the periodic boundary conditions for the one-dimensional carbon nanotubes permit only a few wave vectors to exist around the circumference of carbon nanotubes. Metallic conduction occurs when one of these wave vectors passes through the K-point of graphene’s 2D hexagonal

text: Brillouin zone

text: , where the valence and conduction bands are degenerate. For the semiconducting carbon nanotubes, there is a diameter dependency on bandgap. For example, according to a single-particle tight-binding description of the electronic structure,

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answers: graphene is semiconducting when n – m  3.

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answers: graphene is semiconducting.

text: There are a large number of different valence bond methods. Most use n valence bond orbitals for n electrons. If a single set of these orbitals is combined with all linear independent combinations of the spin functions, we have spin-coupled valence bond theory. The total wave function is optimized using the variational method by varying the coefficients of the basis functions in the valence bond orbitals and the coefficients of the different spin functions. In other cases only a sub-set of all possible spin functions is used. Many valence bond methods use several sets of the valence bond orbitals. Be warned that different authors use different names for these different valence bond methods.

text: There are a large number of different valence bond methods. Most use n valence bond orbitals for n electrons. If a single set of these orbitals is combined with all linear independent combinations of the

text: spin function

text: s, we have spin-coupled valence bond theory. The total

text: wave function

text: is optimized using the

text: variational method

text: by varying the coefficients of the

text: basis functions

text: in the valence bond orbitals and the coefficients of the different spin functions. In other cases only a sub-set of all possible spin functions is used. Many valence bond methods use several sets of the valence bond orbitals. Be warned that different authors use different names for these different valence bond methods.

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answers: valence bond orbitals

text: Callendar effect -Cap and Share -Carbon bubble -Carbon capture and storage -Carbon cycle -Carbon negative -Carbon neutral -Carbon price -Carbon project -Carbon sequestration -Carbon offset -Carbon sink -Carbon tax -Catastrophic climate change -Center for the Study of Carbon Dioxide and Global Change -Clathrate gun hypothesis -Clean coal technology -Clean Energy Trends -Climate -Climate change -Climate change acronyms -Climate Change Act 2008 -Climate change and agriculture -Climate change denial -Climate change feedback -Climate change in Japan -Climate change in popular culture -Climate change mitigation -Climate change mitigation -Climate change mitigation scenarios -Climate commitment -Climate crunch -Climate cycle -Climate engineering -Climate ethics -Climate governance-Climate Investment Funds -Climate model -Climate refugee -Climate risk management -Climate scientists (list) -Climate sensitivity -Climate stabilization wedge -Climate surprise -Climate variability -Climate Vulnerable Forum-Climatic Research Unit email controversy -Cloud feedback -Cloud reflectivity enhancement -Coal phase out -Contraction and Convergence -Contrail -Cool roof -Cool tropics paradox -Coral bleaching

text: Callendar effect

text: Cap and Share

text: Carbon bubble

text: Carbon capture and storage

text: Carbon cycle

text: Carbon negative

text: Carbon neutral

text: Carbon price

text: Carbon project

text: Carbon sequestration

text: Carbon offset

text: Carbon sink

text: Carbon tax

text: Catastrophic climate change

entity_name: Center for the Study of Carbon Dioxide and Global Change

text: Center for the Study of Carbon Dioxide and Global Change

text: Clathrate gun hypothesis

text: Clean coal technology

text: Clean Energy Trends

text: Climate

text: Climate change

text: Climate change acronyms

text: Climate Change Act 2008

text: Climate change and agriculture

text: Climate change denial

text: Climate change feedback

text: Climate change in Japan

text: Climate change in popular culture

text: Climate change mitigation

text: Climate change mitigation

text: Climate change mitigation scenarios

text: Climate commitment

text: Climate crunch

text: Climate cycle

text: Climate engineering

text: Climate ethics

text: Climate governance

text: Climate Investment Funds

text: Climate model

text: Climate refugee

text: Climate risk management

text: Climate scientists (list)

text: Climate sensitivity

text: Climate stabilization wedge

text: Climate surprise

text: Climate variability

text: Climate Vulnerable Forum

entity_name: Climatic Research Unit email controversy

text: Climatic Research Unit email controversy

text: Cloud feedback

text: Cloud reflectivity enhancement

text: Coal phase out

text: Contraction and Convergence

text: Contrail

text: Cool roof

text: Cool tropics paradox

text: Coral bleaching

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answers: Carbon can form more compounds than any other element

text: The skeleton has hydrogen and/or various substituents bonded to its atoms. Hydrogen is the most common non-carbon atom that is bonded to carbon and, for simplicity, is not explicitly drawn. In addition, carbon atoms are not generally labelled as such directly (i.e. with a "C"), whereas heteroatoms are always explicitly noted as such (i.e. using "N" for nitrogen, "O" for oxygen, etc.)

text: The skeleton has hydrogen and/or various

text: substituent

text: s bonded to its atoms. Hydrogen is the most common non-carbon atom that is bonded to carbon and, for simplicity, is not explicitly drawn. In addition, carbon atoms are not generally labelled as such directly (i.e. with a "C"), whereas heteroatoms are always explicitly noted as such (i.e. using "N" for

text: nitrogen

text: , "O" for

text: oxygen

text: , etc.)

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answers: Carbon is not generally labelled as such directly

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answers: It can form more compounds than any other element

text: The same is true when an alkene reacts with water in an addition reaction to form an alcohol which involve formation of carbocations. The hydroxyl group (OH) bonds to the carbon that has the greater number of carbon–carbon bonds, while the hydrogen bonds to the carbon on the other end of the double bond, that has more carbon–hydrogen bonds.

text: The same is true when an alkene reacts with water in an addition reaction to form an alcohol which involve formation of carbocations. The hydroxyl group (OH) bonds to the carbon that has the greater number of carbon–carbon bonds, while the hydrogen bonds to the carbon on the other end of the double bond, that has more carbon–hydrogen bonds.

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answers: carbon–carbon bonds

text: The C–I bond is the weakest of the carbon–halogen bonds.  These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.  This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond. For example, in the molecules represented by CHX, where X is a halide, the carbon-X bonds have strengths, or bond dissociation energies, of 115, 83.7, 72.1, and 57.6 kcal/mol for X = fluoride, chloride, bromide, and iodide, respectively. Of the halides, iodide usually is the best leaving group. Because of the weakness of the C-I bond, samples of organoiodine compounds are often yellow due to an impurity of I.

text: The C–I bond is the weakest of the carbon–

text: halogen

text: bonds.  These bond strengths correlate with the

text: electronegativity

text: of the halogen, decreasing in the order F > Cl > Br > I.  This

text: periodic

text: order also follows the

text: atomic radius

text: of halogens and the length of the carbon-halogen bond. For example, in the molecules represented by CHX, where X is a halide, the carbon-X bonds have strengths, or

text: bond dissociation energies

text: , of 115, 83.7, 72.1, and 57.6 kcal/mol for X = fluoride, chloride, bromide, and iodide, respectively. Of the halides, iodide usually is the best

text: leaving group

text: . Because of the weakness of the C-I bond, samples of organoiodine compounds are often yellow due to an impurity of I.

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answers: F > Cl > Br > I

answers: NDQ_016396

answers: halogen bonds

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answers: halogens

text: A sigmatropic reaction in organic chemistry is a pericyclic reaction wherein the net result is one σ-bond is changed to another σ-bond in an uncatalyzed intramolecular process. The name sigmatropic is the result of a compounding of the long-established sigma designation from single carbon–carbon bonds and the Greek word tropos, meaning turn. In this type of rearrangement reaction, a substituent moves from one part of a π-bonded system to another part in an intramolecular reaction with simultaneous rearrangement of the π system. True sigmatropic reactions are usually uncatalyzed, although Lewis acid catalysis is possible. Sigmatropic reactions often have transition-metal catalysts that form intermediates in analogous reactions. The most well-known of the sigmatropic rearrangements are the [3,3] Cope rearrangement, Claisen rearrangement, Carroll rearrangement and the Fischer indole synthesis.

text: A sigmatropic reaction in

text: organic chemistry

text: is a

text: pericyclic reaction

text: wherein the net result is one

text: σ-bond

text: is changed to another σ-bond in an uncatalyzed

text: intramolecular

text: process. The name sigmatropic is the result of a

text: compounding

text: of the long-established sigma designation from single

text: carbon

text: –carbon bonds and the Greek word tropos, meaning turn. In this type of

text: rearrangement reaction

text: , a

text: substituent

text: moves from one part of a

text: π-bonded

text: system to another part in an intramolecular reaction with simultaneous rearrangement of the π system. True sigmatropic reactions are usually uncatalyzed, although

text: Lewis acid

text: catalysis

text: is possible. Sigmatropic reactions often have transition-metal catalysts that form intermediates in analogous reactions. The most well-known of the sigmatropic rearrangements are the [3,3]

text: Cope rearrangement

text: Claisen rearrangement

text: Carroll rearrangement

text: and the

text: Fischer indole synthesis

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answers: carbon–carbon bonds

text: Valences may also be different from absolute values of oxidation states due to different polarity of bonds. For example, in dichloromethane, CHCl, carbon has valence 4 but oxidation state 0.

text: Valences may also be different from absolute values of oxidation states due to different polarity of bonds. For example, in

text: dichloromethane

text: , CHCl, carbon has valence 4 but oxidation state 0.

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answers: CHCl

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answers: Dichloromethane

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answers: Valences

text: Many pigments make use of conjugated electron systems to absorb visible light, giving rise to strong colors. For example, the long conjugated hydrocarbon chain in beta-carotene leads to its strong orange color. When an electron in the system absorbs a photon of light of the right wavelength, it can be promoted to a higher energy level. A simple model of the energy levels is provided by the quantum-mechanical problem of a one-dimensional particle in a box of length L, representing the movement of a pi electron along a long conjugated chain of carbon atoms. In this model the lowest possible absorption energy corresponds to the energy difference between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO). For a chain of n C=C bonds or 2n carbon atoms in the molecular ground state, there are 2n pi electrons occupying n molecular orbitals, so that the energy gap is

text: Many

text: pigment

text: s make use of conjugated electron systems to absorb

text: visible light

text: , giving rise to strong colors. For example, the long conjugated

text: hydrocarbon

text: chain in

text: beta-carotene

text: leads to its strong orange color. When an electron in the system absorbs a

text: photon

text: of light of the right

text: wavelength

text: , it can be promoted to a higher energy level. A simple model of the energy levels is provided by the

text: quantum-mechanical

text: problem of a one-dimensional

text: particle in a box

text: of length L, representing the movement of a pi electron along a long conjugated chain of carbon atoms. In this model the lowest possible absorption energy corresponds to the energy difference between the highest occupied molecular orbital (

text: HOMO

text: ) and the lowest unoccupied molecular orbital (LUMO). For a chain of n C=C bonds or 2n carbon atoms in the molecular

text: ground state

text: , there are 2n pi electrons occupying n molecular orbitals, so that the energy gap is

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text: Other carbon based compounds and other molecules may be explained in a similar way. For example, ethene (CH) has a double bond between the carbons.

text: Other carbon based compounds and other molecules may be explained in a similar way. For example,

text: ethene

text: (CH) has a double bond between the carbons.

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text: Stemmadenine is a terpene indole alkaloid.  Stemmadenine is believed to be formed from preakuammicine by a carbon-carbon bond cleavage.  Cleavage of a second carbon-carbon bond is thought to form dehydrosecodine.  The enzymes forming stemmadenine and using it as a substrate remain unknown to date.

text: Stemmadenine is a terpene indole alkaloid.  Stemmadenine is believed to be formed from

text: preakuammicine

text: by a carbon-carbon bond cleavage.  Cleavage of a second carbon-carbon bond is thought to form

text: dehydrosecodine

text: .  The enzymes forming stemmadenine and using it as a substrate remain unknown to date.

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answers: carbon-carbon bond cleavage

text: To more easily understand much of the below discussion of reactions involving carboxylic acids it can be helpful to notice that the carboxyl group itself is a "hydroxylated carbonyl group" meaning that two of the carbon atom's four bonds are to an oxygen atom, the carbon atom's third bond is to a second oxygen atom (whose other bond is to a hydrogen atom), and the carbon atom's fourth bond attaches to R. (A carbon atom double bonded to an oxygen atom is a carbonyl group and two of the carbon atom's bonds remain available for bonding. A hydrogen atom bonded to an oxygen atom is a hydroxyl group with the oxygen atom's second bond available for bonding.)

text: To more easily understand much of the below discussion of reactions involving carboxylic acids it can be helpful to notice that the carboxyl group itself is a "hydroxylated carbonyl group" meaning that two of the carbon atom's four bonds are to an oxygen atom, the carbon atom's third bond is to a second oxygen atom (whose other bond is to a hydrogen atom), and the carbon atom's fourth bond attaches to R. (A carbon atom double bonded to an oxygen atom is a

text: carbonyl group

text: and two of the carbon atom's bonds remain available for bonding. A hydrogen atom bonded to an oxygen atom is a

text: hydroxyl group

text: with the oxygen atom's second bond available for bonding.)

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answers: Carboxylic acids

text: Carbon–fluorine bonds are the strongest in organic chemistry. Additionally, they strengthen as more carbon–fluorine bonds are added to the same carbon. In the one carbon organofluorine compounds represented by molecules of fluoromethane, difluoromethane, trifluoromethane, and tetrafluoromethane, the carbon–fluorine bonds are strongest in tetrafluoromethane. This effect is due to the increased coulombic attractions between the fluorine atoms and the carbon because the carbon has a positive partial charge of 0.76.

text: Carbon–fluorine bonds are the strongest in

text: organic chemistry

text: . Additionally, they strengthen as more carbon–fluorine bonds are added to the same carbon. In the one carbon

text: organofluorine compound

text: s represented by molecules of

text: fluoromethane

text: difluoromethane

text: , trifluoromethane, and tetrafluoromethane, the carbon–fluorine bonds are strongest in tetrafluoromethane. This effect is due to the increased

text: coulombic

text: attractions between the fluorine atoms and the carbon because the carbon has a positive

text: partial charge

text: of 0.76.

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answers: carbon–fluorine bonds

text: It was found that the reaction of chymotrypsin with its substrate takes place in two stages, an initial “burst” phase at the beginning of the reaction and a steady-state phase following Michaelis-Menten kinetics. It is also called "ping-pong" mechanism. The mode of action of chymotrypsin explains this as hydrolysis takes place in two steps. First acylation of the substrate to form an acyl-enzyme intermediate and then deacylation in order to return the enzyme to its original state. This occurs via the concerted action of the three amino acid residues in the catalytic triad.  Aspartate hydrogen bonds to the N-δ hydrogen of histidine, increasing the pKa of its ε nitrogen and thus making it able to deprotonate serine. It is this deprotonation that allows the serine side chain to act as a nucleophile and bind to the electron-deficient carbonyl carbon of the protein main chain. Ionization of the carbonyl oxygen is stabilized by formation of two hydrogen bonds to adjacent main chain N-hydrogens. This occurs in the oxyanion hole. This forms a tetrahedral adduct and breakage of the peptide bond. An acyl-enzyme intermediate, bound to the serine, is formed, and the newly formed amino terminus of the cleaved protein can dissociate. In the second reaction step, a water molecule is activated by the basic histidine, and acts as a nucleophile. The oxygen of water attacks the carbonyl carbon of the serine-bound acyl group, resulting in formation of a second tetrahedral adduct, regeneration of the serine -OH group, and release of a proton, as well as the protein fragment with the newly formed carboxyl terminus

text: It was found that the reaction of chymotrypsin with its substrate takes place in two stages, an initial “burst” phase at the beginning of the reaction and a steady-state phase following

text: Michaelis-Menten kinetics

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answers: carbonyl carbon

text: Discovered in 1912 by Rainer Ludwig Claisen, the Claisen rearrangement is the first recorded example of a [3,3]-sigmatropic rearrangement. This rearrangement is a useful carbon-carbon bond-forming reaction. An example of Claisen rearrangement is the [3,3] rearrangement of an allyl vinyl ether, which upon heating yields a γ,δ-unsaturated carbonyl. The formation of a carbonyl group makes this reaction, unlike other sigmatropic rearrangements, inherently irreversible.

text: Discovered in 1912 by

text: Rainer Ludwig Claisen

text: , the Claisen rearrangement is the first recorded example of a [3,3]-sigmatropic rearrangement. This rearrangement is a useful

text: carbon

text: -carbon

text: bond

text: -forming

text: reaction

text: . An example of Claisen rearrangement is the [3,3] rearrangement of an

text: allyl

text: vinyl

text: ether

text: , which upon heating yields a γ,δ-unsaturated carbonyl. The formation of a carbonyl group makes this reaction, unlike other sigmatropic rearrangements, inherently irreversible.

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answers: inherently irreversible

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text: In chemistry, a tetravalence is the state of an atom with four electrons available for covalent chemical bonding in its valence (outermost electron shell). An example is methane (CH): the tetravalent carbon atom forms a covalent bond with four hydrogen atoms. The carbon atom is called tetravalent because it forms 4 covalent bonds.A carbon atom has a total of six electrons occupying the first two shells, i.e., the K-shell has two electrons and the L-shell has four electrons. This distribution indicates that in the outermost shell there are one completely filled 's' orbital and two half-filled 'p' orbitals, showing carbon to be a divalent atom. But in actuality, carbon displays tetravalency in the combined state. Therefore, a carbon atom has four valence electrons. It could gain four electrons to form the C anion or lose four electrons to form the C cation. Both these conditions would take carbon far away from achieving stability by the octet rule. To overcome this problem carbon undergoes bonding by sharing its valence electrons. This allows it to be covalently bonded to one, two, three or four carbon atoms or atoms of other elements or groups of atoms. Let us see how carbon forms the single, double and triple bonds in the following examples.

text: In

text: chemistry

text: , a tetravalence is the state of an

text: atom

text: with four

text: electron

text: s available for

text: covalent

text: chemical bond

text: ing in its

text: valence

text: (outermost

text: electron shell

text: ). An example is

text: methane

text: (CH): the tetravalent

text: carbon

text: atom forms a covalent bond with four

text: hydrogen atom

text: s. The carbon atom is called tetravalent because it forms 4 covalent bonds.A carbon atom has a total of six electrons occupying the first two shells, i.e., the K-shell has two electrons and the L-shell has four electrons. This distribution indicates that in the outermost shell there are one completely filled 's' orbital and two half-filled 'p' orbitals, showing carbon to be a

text: divalent atom

text: . But in actuality, carbon displays tetravalency in the combined state. Therefore, a carbon atom has four valence electrons. It could gain four electrons to form the C

text: anion

text: or lose four electrons to form the C

text: cation

text: . Both these conditions would take carbon far away from achieving stability by the

text: octet rule

text: . To overcome this problem carbon undergoes bonding by sharing its valence electrons. This allows it to be covalently bonded to one, two, three or four carbon atoms or atoms of other elements or groups of atoms. Let us see how carbon forms the single, double and triple bonds in the following examples.

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answers: The carbon atom is called tetravalent because it forms 4 covalent bonds

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answers: hydrogen atoms

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answers: methane

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answers: It could gain four electrons to form the C anion

text: Polystyrene results when styrene monomers interconnect. In the polymerization, the carbon-carbon pi bond (in the vinyl group) is broken and a new carbon-carbon single (sigma) bond is formed, attaching another styrene monomer to the chain.  The newly formed sigma bond is much stronger than the pi bond that was broken, thus it is very difficult to depolymerize polystyrene.  About a few thousand monomers typically comprise a chain of polystyrene, giving a molecular weight of 100,000–400,000.

text: Polystyrene results when styrene monomers interconnect. In the polymerization, the carbon-carbon pi bond (in the

text: vinyl

text: group) is broken and a new carbon-carbon single (sigma) bond is formed, attaching another styrene monomer to the chain.  The newly formed sigma bond is much stronger than the pi bond that was broken, thus it is very difficult to depolymerize polystyrene.  About a few thousand monomers typically comprise a chain of polystyrene, giving a

text: molecular weight

text: of 100,000–400,000.

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answers: polymerization

text: The rigidity of cumulenes arises from the fact that the internal carbon atoms carry two double bonds. Their sp hybridisation results in two bonds separated by 90°. Cumulenes with (1) an even number of consecutive double bonds and (2) dissimilar substituents on either end can be chiral even though they lack a classical stereocenter. On the other hand odd numbers of double bonds in a cumulated system with proper substituents show cis–trans isomerism.

text: The rigidity of cumulenes arises from the fact that the internal carbon atoms carry two double bonds. Their sp hybridisation results in two bonds separated by 90°. Cumulenes with (1) an even number of consecutive double bonds and (2) dissimilar substituents on either end can be chiral even though they lack a classical stereocenter. On the other hand odd numbers of double bonds in a cumulated system with proper substituents show

text: cis–trans isomerism

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answers: Cumulenes

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text: Nonmetals have structures in which each atom usually forms (8 − N) bonds with (8 − N) nearest neighbours, where N is the number of valence electrons. Each atom is thereby able to complete its valence shell and attain a stable noble gas configuration. Exceptions to the (8 − N) rule occur with hydrogen (which only needs one bond to complete its valence shell), carbon, nitrogen and oxygen. Atoms of the latter three elements are sufficiently small such that they are able to form alternative (more stable) bonding structures, with fewer nearest neighbours. Thus, carbon is able to form its layered graphite structure, and nitrogen and oxygen are able to form diatomic molecules having triple and double bonds, respectively. The larger size of the remaining non-noble nonmetals weakens their capacity to form multiple bonds and they instead form two or more single bonds to two or more different atoms. Sulfur, for example, forms an eight-membered molecule in which the atoms are arranged in a ring, with each atom forming two single bonds to different atoms.

text: Nonmetals have structures in which each atom usually forms (8 − N) bonds with (8 − N)

text: nearest neighbours

text: , where N is the number of

text: valence electron

text: s. Each atom is thereby able to complete its

text: valence shell

text: and attain a stable noble gas configuration. Exceptions to the (8 − N) rule occur with hydrogen (which only needs one bond to complete its valence shell), carbon, nitrogen and oxygen. Atoms of the latter three elements are sufficiently small such that they are able to form alternative (more stable) bonding structures, with fewer nearest neighbours. Thus, carbon is able to form its layered

text: graphite

text: structure, and nitrogen and oxygen are able to form diatomic molecules having

text: triple

text: and

text: double bond

text: s, respectively. The larger size of the remaining non-noble nonmetals weakens their capacity to form multiple bonds and they instead form two or more

text: single bond

text: s to two or more different atoms. Sulfur, for example, forms an eight-membered molecule in which the atoms are arranged in a ring, with each atom forming two single bonds to different atoms.

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answers: atoms of the latter three elements are sufficiently small

text: The driving force for the addition to alkenes is the formation of a nucleophile X that forms a covalent bond with an electron-poor unsaturated system -C=C- (step 1). The negative charge on X is transferred to the carbon – carbon bond.

text: The driving force for the addition to

text: alkenes

text: is the formation of a

text: nucleophile

text: X that forms a

text: covalent bond

text: with an electron-poor

text: unsaturated

text: system -C=C- (step 1). The negative charge on X is transferred to the carbon – carbon bond.

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answers: alkenes

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text: Like a single covalent bond, double bonds can be described in terms of overlapping atomic orbitals, except that, unlike a single bond (which consists of a single sigma bond), a carbon–carbon double bond consists of one sigma bond and one pi bond. This double bond is stronger than a single covalent bond (611 kJ/mol for C=C vs. 347 kJ/mol for C–C) and also shorter, with an average bond length of 1.33 ångströms (133 pm).

text: Like a single

text: covalent bond

text: , double bonds can be described in terms of overlapping

text: atom

text: ic orbitals, except that, unlike a single bond (which consists of a single

text: sigma bond

text: ), a carbon–carbon double bond consists of one

text: sigma bond

text: and one

text: pi bond

text: . This double bond is stronger than a single

text: covalent bond

text: kJ

text: mol

text: for C=C vs. 347 kJ/mol for C–C) and also shorter, with an average

text: bond length

text: of 1.33

text: ångström

text: s (133

text: pm

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text: The concept first appeared in 1899 in Johannes Thiele's "Partial Valence Hypothesis" to explain the unusual stability of benzene which would not be expected from August Kekulé's structure proposed in 1865 with alternating single and double bonds. Benzene undergoes substitution reactions, rather than addition reactions as typical for alkenes. He proposed that the carbon-carbon bond in benzene is intermediate of a single and double bond.

text: The concept first appeared in 1899 in

text: Johannes Thiele

text: 's "Partial Valence Hypothesis" to explain the unusual stability of benzene which would not be expected from

text: August Kekulé

text: 's structure proposed in 1865 with alternating single and double bonds. Benzene undergoes substitution reactions, rather than addition reactions as typical for

text: alkene

text: s. He proposed that the carbon-carbon bond in benzene is intermediate of a single and double bond.

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text: With reactive metals, such as tungsten, carbon forms either carbides (C) or acetylides () to form alloys with high melting points. These anions are also associated with methane and acetylene, both very weak acids. With an electronegativity of 2.5, carbon prefers to form covalent bonds. A few carbides are covalent lattices, like carborundum (SiC), which resembles diamond. Nevertheless, even the most polar and salt-like of carbides are not completely ionic compounds.

text: With reactive

text: metal

text: s, such as

text: tungsten

text: , carbon forms either

text: carbide

text: s (C) or

text: acetylide

text: s () to form alloys with high melting points. These anions are also associated with

text: methane

text: and

text: acetylene

text: , both very weak

text: acid

text: s. With an electronegativity of 2.5, carbon prefers to form

text: covalent bond

text: s. A few carbides are covalent lattices, like

text: carborundum

text: (SiC), which resembles

text: diamond

text: . Nevertheless, even the most polar and salt-like of carbides are not completely ionic compounds.

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answers: With an electronegativity of 2.5

text: Cellocidin is an organic compound containing 4 carbon atoms, 4 hydrogen atoms, 2 oxygen atoms, and 2 nitrogen atoms. It contains one carbon-carbon triple bond between carbons 2 and 3, and two carbon-oxygen double bonds off carbon 1 and carbon 4. 2-butynediamide contains two identical amide groups connected together by the central carbons (carbons 2 and 3).

text: Cellocidin is an

text: organic compound

text: containing 4

text: carbon

text: atoms

text: , 4

text: hydrogen

text: atoms

text: , 2

text: oxygen

text: atoms

text: , and 2

text: nitrogen

text: atoms

text: . It contains one carbon-carbon

text: triple bond

text: between carbons 2 and 3, and two carbon-oxygen

text: double bond

text: s off carbon 1 and carbon 4. 2-butynediamide contains two identical

text: amide groups

text: connected together by the central carbons (carbons 2 and 3).

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answers: Cellocidin

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answers: Cellocidin

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answers: carbon-carbon triple bond

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answers: carbon-oxygen double bonds

text: In simple chemistry, as per valence bond theory, the carbon atom must follow the "4-hydrogen rule", which states that the maximum number of atoms available to bond with carbon is equal to the number of electrons that are attracted into the outer shell of carbon. In terms of shells, carbon consists of an incomplete outer shell, which comprises 4 electrons, and thus has 4 electrons available for covalent or dative bonding.

text: In simple chemistry, as per

text: valence bond theory

text: , the carbon atom must follow the "4-hydrogen rule", which states that the maximum number of atoms available to bond with carbon is equal to the number of electrons that are attracted into the outer shell of carbon. In terms of shells, carbon consists of an incomplete outer shell, which comprises 4 electrons, and thus has 4 electrons available for covalent or

text: dative bonding

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text: Phosphinimide tantalum complexes are producible through the straightforward method of adding RPNSiMe to Cp and Cl coordinated Ta complexes. The resulting RPNTa(Cp)Cl complex can be alkylidated with Me or CHPh. In the addition of CHPh through its Grignard reagent, an alkylidene complex is formed, steming from one CHPh adding as the alkylidene and the other coordinating as a single bond. If MeI is introduced, the alkylidene is transformed to a metallocycle, with the Me bonding to the metal coordinated carbon and the metal. Similarly, the addition of EtMgCl forms a metallocycle, with the second equivalent displacing the Cl and coordinating as Et. Finally, cationic complexes can also be formed, generally through the addition of B(CF). If added to the alkylidated Ta phosphinimide with PhC, a methyl group is dissociated; however, if added to the metallocycle, the PhC will bond to one of the carbons of the metallocycle, breaking its bond with the metal. If the PhC is left out and only B(CF) is used instead, the boron atom will open the ring by bonding to one of the metal, leaving a negative charge on the boron and a positive charge on the metal.

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text: Commonly, the natural oils are hydrogenated by passing hydrogen through the oil in the presence of a nickel catalyst, under controlled conditions. The addition of hydrogen to the unsaturated bonds (alkenic double C=C bonds) results in saturated C-C bonds, effectively increasing the melting point of the oil and thus "hardening" it. This is due to the increase in van der Waals' forces between the saturated molecules compared with the unsaturated molecules. However, as there are possible health benefits in limiting the amount of saturated fats in the human diet, the process is controlled so that only enough of the bonds are hydrogenated to give the required texture. Margarines made in this way are said to contain hydrogenated fat. This method is used today for some margarines although the process has been developed and sometimes other metal catalysts are used such as palladium. If hydrogenation is incomplete (partial hardening), the relatively high temperatures used in the hydrogenation process tend to flip some of the carbon-carbon double bonds into the "trans" form. If these particular bonds aren't hydrogenated during the process, they remain present in the final margarine in molecules of trans fats, the consumption of which has been shown to be a risk factor for cardiovascular disease. For this reason, partially hardened fats are used less and less in the margarine industry. Some tropical oils, such as palm oil and coconut oil, are naturally semi-solid and do not require hydrogenation.

text: Commonly, the natural oils are hydrogenated by passing

text: hydrogen

text: through the oil in the presence of a

text: nickel

text: catalyst

text: , under controlled conditions. The addition of hydrogen to the unsaturated bonds (alkenic double C=C bonds) results in saturated C-C bonds, effectively increasing the melting point of the oil and thus "hardening" it. This is due to the increase in

text: van der Waals' force

text: s between the saturated molecules compared with the unsaturated molecules. However, as there are possible health benefits in limiting the amount of saturated fats in the human diet, the process is controlled so that only enough of the bonds are hydrogenated to give the required texture. Margarines made in this way are said to contain hydrogenated fat. This method is used today for some margarines although the process has been developed and sometimes other metal catalysts are used such as

text: palladium

text: . If hydrogenation is incomplete (partial hardening), the relatively high temperatures used in the hydrogenation process tend to flip some of the carbon-carbon double bonds into the "trans" form. If these particular bonds aren't hydrogenated during the process, they remain present in the final margarine in molecules of

text: trans fats

text: , the consumption of which has been shown to be a risk factor for

text: cardiovascular disease

text: . For this reason, partially hardened fats are used less and less in the margarine industry. Some tropical oils, such as

text: palm oil

text: and

text: coconut oil

text: , are naturally semi-solid and do not require hydrogenation.

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text: The mechanistic discussion on whether the vinylcyclopropane rearrangement proceeds through a diradical-mediated two-step or a fully concerted orbital-symmetry-controlled mechanism has been going on for more than half a century. Kinetic data together with the secondary kinetic isotope effects observed at the vinyl terminus of the vinylcyclopropane suggest a concerted mechanism whereas product distribution indicates a stepwise-diradical mechanism.In the 1960s, shortly after the rearrangement was discovered, it was established that the activation energy for the vinylcyclopropane rearrangement is around 50 kcal/mol. The kinetic data obtained for this rearrangement were consistent with a concerted mechanism where cleavage of the cyclopropyl carbon-carbon bond was rate-limiting. Albeit a concerted mechanism seemed likely it was shortly recognized that the activation energy to break the carbon-carbon bond in unsubstituted cyclopropane was with 63 kcal/mol exactly 13 kcal/mol higher in energy than the parent activation energy, a difference remarkably similar to the resonance energy of the allyl radical. Immediately people started to appreciate the possibility for a diradical intermediate arising from homolytic cleavage of the weak C1-C2-cyclopropane bond under thermal conditions.

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text: Conductivity of molecular solids can be illustrated on example of fullerene. Its solid is an insulator because all valence electrons of carbon atoms are involved into the covalent bonds within the individual carbon molecules. However, inserting (intercalating) alkali metal atoms between the fullerene molecules provides extra electrons, which can be easily ionized from the metal atoms and make material conductive and even superconductive.

text: Conductivity of molecular solids can be illustrated on example of fullerene. Its solid is an insulator because all valence electrons of carbon atoms are involved into the covalent bonds within the individual carbon molecules. However, inserting (intercalating)

text: alkali metal

text: atoms between the fullerene molecules provides extra electrons, which can be easily ionized from the metal atoms and make material conductive and even

text: superconductive

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text: The method is not limited to the preparation of amines, it can also be used to form Carbon–carbon bonds (C-C bonds).

text: The method is not limited to the preparation of amines, it can also be used to form

text: Carbon–carbon bond

text: s (C-C bonds).

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answers: Carbon–carbon bonds

text: In chemistry and materials science, a single type of atom may form allotropes with different physical properties from each other, and from their individual constituent atoms, such as diamond and graphite each consisting of carbon atoms. What is true of a single carbon atom is not true of a collection of carbon atoms bonded into a material. Furthermore, the properties of an atom differ from the properties of the individual subatomic particles that constitute it.

text: In

text: chemistry

text: and

text: materials science

text: , a single type of

text: atom

text: may form

text: allotropes

text: with different physical properties from each other, and from their individual constituent atoms, such as

text: diamond

text: and

text: graphite

text: each consisting of

text: carbon

text: atoms. What is true of a single carbon atom is not true of a collection of carbon atoms bonded into a material. Furthermore, the properties of an atom differ from the properties of the individual

text: subatomic particle

text: s that constitute it.

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answers: Allotropes

text: In chemistry, the hydrogenation of carbon–nitrogen double bonds is the addition of the elements of dihydrogen (H) across a carbon–nitrogen double bond, forming amines or amine derivatives. Although a variety of general methods have been developed for the enantioselective hydrogenation of ketones, methods for the hydrogenation of carbon–nitrogen double bonds are less general. Hydrogenation of imines is complicated by both syn/anti isomerization and tautomerization to enamines, which may be hydrogenated with low enantioselectivity in the presence of a chiral catalyst. Additionally, the substituent attached to nitrogen affects both the reactivity and spatial properties of the imine, complicating the development of a general catalyst system for imine hydrogenation. Despite these challenges, methods have been developed that address particular substrate classes, such as N-aryl, N-alkyl, and endocyclic imines.

text: In chemistry, the hydrogenation of carbon–nitrogen double bonds is the addition of the elements of dihydrogen (H) across a carbon–nitrogen double bond, forming amines or amine derivatives. Although a variety of general methods have been developed for the enantioselective hydrogenation of ketones, methods for the hydrogenation of carbon–nitrogen double bonds are less general. Hydrogenation of imines is complicated by both syn/anti isomerization and tautomerization to enamines, which may be hydrogenated with low enantioselectivity in the presence of a chiral catalyst. Additionally, the substituent attached to nitrogen affects both the reactivity and spatial properties of the imine, complicating the development of a general catalyst system for imine hydrogenation. Despite these challenges, methods have been developed that address particular substrate classes, such as N-aryl, N-alkyl, and endocyclic imines.

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answers: carbon–nitrogen double bonds

answers: NDQ_016396

answers: double bonds

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answers: ketones

answers: NDQ_016399

answers: amines

answers: NDQ_016400

answers: two

answers: NDQ_016401

answers: Nitrogen

text: True amorphous carbon has localized π electrons (as opposed to the aromatic π bonds in graphite), and its bonds form with lengths and distances that are inconsistent with any other allotrope of carbon.  It also contains a high concentration of dangling bonds; these cause deviations in interatomic spacing (as measured using diffraction) of more than 5% as well as noticeable variation in bond angle.

text: True amorphous carbon has localized π electrons (as opposed to the

text: aromatic

text: π bond

text: s in graphite), and its bonds form with lengths and distances that are inconsistent with any other

text: allotrope

text: of carbon

text: .  It also contains a high concentration of dangling bonds; these cause deviations in interatomic spacing (as measured using

text: diffraction

text: ) of more than 5% as well as noticeable variation in bond angle.

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answers: True amorphous carbon

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answers: graphite

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answers: dangling bonds

text: Hydrolysis, a reaction in which water breaks a bond, is a good example of the nucleophilic nature of haloalkanes. The polar bond attracts a hydroxide ion, OH (NaOH being a common source of this ion). This OH is a nucleophile with a clearly negative charge, as it has excess electrons it donates them to the carbon, which results in a covalent bond between the two. Thus C–X is broken by heterolytic fission resulting in a halide ion, X. As can be seen, the OH is now attached to the alkyl group, creating an alcohol. (Hydrolysis of bromoethane, for example, yields ethanol). Reaction with ammonia give primary amines.

text: Hydrolysis

text: , a reaction in which

text: water

text: breaks a bond, is a good example of the nucleophilic nature of haloalkanes. The polar bond attracts a

text: hydroxide

text: ion, OH (NaOH being a common source of this ion). This OH is a nucleophile with a clearly negative charge, as it has excess electrons it donates them to the carbon, which results in a

text: covalent

text: bond between the two. Thus C–X is broken by

text: heterolytic fission

text: resulting in a halide ion, X. As can be seen, the OH is now attached to the alkyl group, creating an

text: alcohol

text: . (Hydrolysis of bromoethane, for example, yields

text: ethanol

text: ). Reaction with ammonia give primary amines.

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answers: C–X

answers: NDQ_016396

answers: covalent bond

answers: NDQ_016398

answers: haloalkanes

answers: NDQ_016399

answers: C–X

answers: NDQ_016400

answers: C–X

answers: NDQ_016401

answers: C–X

text: There are two main explanations for the gauche effect: hyperconjugation and bent bonds. In the hyperconjugation model, the donation of electron density from the carbon–hydrogen σ bonding orbital to the carbon–fluorine σ antibonding orbital is considered the source of stabilization in the gauche isomer. Due to the greater electronegativity of fluorine, the carbon–hydrogen σ orbital is a better electron donor than the carbon–fluorine σ orbital, while the carbon–fluorine σ orbital is a better electron acceptor than the carbon–hydrogen σ orbital. Only the gauche conformation allows good overlap between the better donor and the better acceptor.

text: There are two main explanations for the gauche effect:

text: hyperconjugation

text: and

text: bent bond

text: s. In the hyperconjugation model, the donation of electron density from the carbon–hydrogen σ bonding orbital to the carbon–fluorine σ antibonding orbital is considered the source of stabilization in the gauche isomer. Due to the greater electronegativity of fluorine, the carbon–hydrogen σ orbital is a better electron donor than the carbon–fluorine σ orbital, while the carbon–fluorine σ orbital is a better electron acceptor than the carbon–hydrogen σ orbital. Only the gauche conformation allows good overlap between the better donor and the better acceptor.

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answers: due to the greater electronegativity of fluorine

text: Silicone resins are partly organic in nature with a backbone polymer structure made of alternating silicon and oxygen atoms rather than the familiar carbon-to-carbon backbone characteristics of organic polymers. In addition to having at least one oxygen atom bonded to each silicone atom, silicone resins have direct bonds to carbon and therefore also known as polyorganosiloxanes. They have the general formula (R2SiO)n and the physical form (liquid, gel, elastomer or solid) and use varies with molecular weight, structure (linear, branched, caged) and nature of substituent groups (R = alkyl, aryl, H, OH, alkoxy). Aryl substituted silicone resins have greater thermal stability than alkyl substituted silicone resins when polymerised (condensation cure mechanism) at temperatures between ~300 °F (~150 °C) and ~400 °F (~200 °C). Heating above ~600 °F (~ 300 °C) converts all silicone polymers into ceramics since all organic constituents pyrolytically decompose leaving crystalline silicate polymers with the general formula (-SiO2-)n. In addition to applications as ceramic matrix composite precursors, silicone resins in the form of polysiloxane polymers made from silicone resins with pendant acrylate, vinyl ether or epoxy functionality find application as UV, electron beam and thermoset polymer matrix composites where they are characterised by their resistance to oxidation, heat and ultraviolet degradation.

text: Silicone resins

text: are partly organic in nature with a backbone polymer structure made of alternating

text: silicon

text: and

text: oxygen

text: atom

text: s rather than the familiar

text: carbon

text: -to-carbon backbone characteristics of organic polymers. In addition to having at least one oxygen atom bonded to each silicone atom, silicone resins have direct bonds to carbon and therefore also known as polyorganosiloxanes. They have the general formula (R2SiO)n and the physical form (liquid, gel, elastomer or solid) and use varies with molecular weight, structure (linear, branched, caged) and nature of substituent groups (R = alkyl, aryl, H, OH, alkoxy). Aryl substituted silicone resins have greater thermal stability than alkyl substituted silicone resins when polymerised (condensation cure mechanism) at temperatures between ~300 °F (~150 °C) and ~400 °F (~200 °C). Heating above ~600 °F (~ 300 °C) converts all silicone polymers into ceramics since all organic constituents pyrolytically decompose leaving crystalline silicate polymers with the general formula (-SiO2-)n. In addition to applications as

text: ceramic matrix composite

text: precursors, silicone resins in the form of polysiloxane polymers made from silicone resins with pendant acrylate, vinyl ether or epoxy functionality find application as UV, electron beam and thermoset polymer matrix composites where they are characterised by their resistance to oxidation, heat and ultraviolet degradation.

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answers: carbon

text: While researching these reducing agents, Brown’s coworker, Dr. B. C. Subba Rao, discovered an unusual reaction between sodium borohydride and ethyl oleate. The borohydride added hydrogen and boron to the carbon-carbon double bond in the ethyl oleate. The organoborane product could then be oxidized to form an alcohol. This two-step reaction is now called hydroboration-oxidation and is a reaction that converts alkenes into anti-Markovnikov alcohols. Markovnikov's rule states that, in adding hydrogen and a halide or hydroxyl group to a carbon-carbon double bond, the hydrogen is added to the less-substituted carbon of the bond and the hydroxyl or halide group is added to the more-substituted carbon of the bond. In hydroboration-oxidation, the opposite addition occurs.

text: While researching these reducing agents, Brown’s coworker, Dr. B. C. Subba Rao, discovered an unusual reaction between sodium borohydride and

text: ethyl oleate

text: . The borohydride added hydrogen and boron to the carbon-carbon

text: double bond

text: in the ethyl oleate. The organoborane product could then be

text: oxidized

text: to form an alcohol. This two-step reaction is now called

text: hydroboration-oxidation

text: and is a reaction that converts

text: alkenes

text: into anti-Markovnikov alcohols.

text: Markovnikov's rule

text: states that, in adding hydrogen and a

text: halide

text: or

text: hydroxyl

text: group to a carbon-carbon double bond, the hydrogen is added to the less-substituted carbon of the bond and the hydroxyl or halide group is added to the more-substituted carbon of the bond. In hydroboration-oxidation, the opposite addition occurs.

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answers: carbon-carbon double bond

text: In terms of valence bond theory, in each carbon atom the 2s orbital hybridizes with one 2p orbital thus forming an sp hybrid. The other two 2p orbitals remain unhybridized. The two ends of the two sp hybrid orbital overlap to form a strong σ valence bond between the carbons, while on each of the other two ends hydrogen atoms attach also by σ bonds. The two unchanged 2p orbitals form a pair of weaker π bonds.

text: In terms of

text: valence bond theory

text: , in each carbon atom the 2s

text: orbital

text: hybridizes

text: with one 2p orbital thus forming an sp hybrid. The other two 2p orbitals remain unhybridized. The two ends of the two sp hybrid

text: orbital overlap

text: to form a strong

text: σ valence bond

text: between the carbons, while on each of the other two ends hydrogen atoms attach also by σ bonds. The two unchanged 2p orbitals form a pair of weaker

text: π bonds

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text: In the methane molecule for example, ab initio calculations show bonding character in four molecular orbitals, sharing the electrons uniformly among all five atoms. There are two orbital levels, a bonding molecular orbital formed from the 2s orbital on carbon and triply degenerate bonding molecular orbitals from each of the 2p orbitals on carbon. The localized sp orbitals corresponding to each individual bond in valence bond theory can be obtained from a linear combination of the four molecular orbitals.

text: In the methane molecule for example, ab initio calculations show bonding character in four molecular orbitals, sharing the electrons uniformly among all five atoms. There are two orbital levels, a bonding molecular orbital formed from the 2s orbital on carbon and triply degenerate bonding molecular orbitals from each of the 2p orbitals on carbon. The localized sp orbitals corresponding to each individual bond in

text: valence bond theory

text: can be obtained from a linear combination of the four molecular orbitals.

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text: However, silicon has several drawbacks as an alternative to carbon. Silicon, unlike carbon, lacks the ability to form chemical bonds with diverse types of atoms as is necessary for the chemical versatility required for metabolism. Elements creating organic functional groups with carbon include hydrogen, oxygen, nitrogen, phosphorus, sulfur, and metals such as iron, magnesium, and zinc. Silicon, on the other hand, interacts with very few other types of atoms. Moreover, where it does interact with other atoms, silicon creates molecules that have been described as "monotonous compared with the combinatorial universe of organic macromolecules". This is because silicon atoms are much bigger, having a larger mass and atomic radius, and so have difficulty forming double bonds (the double bonded carbon is part of the carbonyl group, a fundamental motif of bio-organic chemistry).

text: However, silicon has several drawbacks as an alternative to carbon. Silicon, unlike carbon, lacks the ability to form chemical bonds with diverse types of atoms as is necessary for the chemical versatility required for metabolism. Elements creating organic functional groups with carbon include hydrogen, oxygen, nitrogen, phosphorus, sulfur, and metals such as iron, magnesium, and zinc. Silicon, on the other hand, interacts with very few other types of atoms. Moreover, where it does interact with other atoms, silicon creates molecules that have been described as "monotonous compared with the combinatorial universe of organic macromolecules". This is because silicon atoms are much bigger, having a larger

text: mass

text: and

text: atomic radius

text: , and so have difficulty forming double bonds (the double bonded carbon is part of the

text: carbonyl

text: group, a fundamental motif of bio-organic chemistry).

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text: Some intermetallic materials e.g. do exhibit metal clusters, reminiscent of molecules and these compounds are more a topic of chemistry than of metallurgy. The formation of the clusters could be seen as a way to 'condense out' (localize) the electron deficient bonding into bonds of a more localized nature. Hydrogen is an extreme example of this form of condensation. At high pressures it is a metal. The core of the planet Jupiter could be said to be held together by a combination of metallic bonding and high pressure induced by gravity. At lower pressures however the bonding becomes entirely localized into a regular covalent bond. The localization is so complete that the (more familiar) H gas results. A similar argument holds for an element like boron. Though it is electron deficient compared to carbon, it does not form a metal. Instead it has a number of complicated structures in which icosahedral B clusters dominate. Charge density waves are a related phenomenon.

text: Some intermetallic materials e.g. do exhibit

text: metal cluster

text: s, reminiscent of molecules and these compounds are more a topic of chemistry than of metallurgy. The formation of the clusters could be seen as a way to 'condense out' (localize) the electron deficient bonding into bonds of a more localized nature.

text: Hydrogen

text: is an extreme example of this form of condensation. At high pressures

text: it is a metal

text: . The core of the planet

text: Jupiter

text: could be said to be held together by a combination of metallic bonding and high pressure induced by gravity. At lower pressures however the bonding becomes entirely localized into a regular covalent bond. The localization is so complete that the (more familiar) H gas results. A similar argument holds for an element like boron. Though it is electron deficient compared to carbon, it does not form a metal. Instead it has a number of complicated structures in which

text: icosahedral

text: B clusters dominate.

text: Charge density wave

text: s are a related phenomenon.

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text: A secondary determinant of quality was found to be the fractional content of hydrogen. Some of the production methods involve hydrogen or methane as a catalyst and a considerable percentage of hydrogen can remain in the finished DLC material. When it is recalled that the soft plastic, polyethylene is made from carbon that is bonded purely by the diamond-like sp bonds, but also includes chemically bonded hydrogen, it is not surprising to learn that fractions of hydrogen remaining in DLC films degrade them almost as much as do residues of sp bonded carbon. The VDI2840 report confirmed the utility of locating a particular DLC material onto a 2-dimensional map on which the X-axis described the fraction of hydrogen in the material and the Y-axis described the fraction of sp bonded carbon atoms. The highest quality of diamond-like properties was affirmed to be correlated with the proximity of the map point plotting the (X,Y) coordinates of a particular material to the upper left corner at (0,1), namely 0% hydrogen and 100% sp bonding. That "pure" DLC material is ta-C and others are approximations that are degraded by diluents such as hydrogen, sp bonded carbon, and metals. Valuable properties of materials that are ta-C, or nearly ta-C follow.

text: A secondary determinant of quality was found to be the fractional content of hydrogen. Some of the production methods involve hydrogen or

text: methane

text: as a catalyst and a considerable percentage of hydrogen can remain in the finished DLC material. When it is recalled that the soft plastic,

text: polyethylene

text: is made from carbon that is bonded purely by the diamond-like sp bonds, but also includes chemically bonded hydrogen, it is not surprising to learn that fractions of hydrogen remaining in DLC films degrade them almost as much as do residues of sp bonded carbon. The VDI2840 report confirmed the utility of locating a particular DLC material onto a 2-dimensional map on which the X-axis described the fraction of hydrogen in the material and the Y-axis described the fraction of sp bonded carbon atoms. The highest quality of diamond-like properties was affirmed to be correlated with the proximity of the map point plotting the (X,Y) coordinates of a particular material to the upper left corner at (0,1), namely 0% hydrogen and 100% sp bonding. That "pure" DLC material is ta-C and others are approximations that are degraded by diluents such as hydrogen, sp bonded carbon, and metals. Valuable properties of materials that are ta-C, or nearly ta-C follow.

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text: Biologically synthesized organofluorines have been found in microorganisms and plants, but not animals. The most common example is fluoroacetate, which occurs as a plant defence against herbivores in at least 40 plants in Australia, Brazil and Africa. Other biologically synthesized organofluorines include ω-fluoro fatty acids, fluoroacetone, and 2-fluorocitrate which are all believed to be biosynthesized in biochemical pathways from the intermediate fluoroacetaldehyde. Adenosyl-fluoride synthase is an enzyme capable of biologically synthesizing the carbon–fluorine bond. Man made carbon–fluorine bonds are commonly found in pharmaceuticals and agrichemicals because it adds stability to the carbon framework; also, the relatively small size of fluorine is convenient as fluorine acts as an approximate bioisostere of the hydroxyl group. Introducing the carbon–fluorine bond to organic compounds is the major challenge for medicinal chemists using organofluorine chemistry, as the carbon–fluorine bond increases the probability of having a successful drug by about a factor of ten. An estimated 20% of pharmaceuticals, and 30–40% of agrichemicals are organofluorines, including several of the top drugs. Examples include 5-fluorouracil, fluoxetine (Prozac), paroxetine (Paxil), ciprofloxacin (Cipro), mefloquine, and fluconazole.

text: Biologically synthesized organofluorines have been found in microorganisms and plants, but not animals. The most common example is fluoroacetate, which occurs as a

text: plant defence against herbivores

text: in at least 40 plants in Australia, Brazil and Africa. Other biologically synthesized organofluorines include ω-fluoro

text: fatty acid

text: s, fluoroacetone, and

text: which are all believed to be biosynthesized in biochemical pathways from the intermediate fluoroacetaldehyde.

text: Adenosyl-fluoride synthase

text: is an enzyme capable of biologically synthesizing the carbon–fluorine bond. Man made carbon–fluorine bonds are commonly found in pharmaceuticals and

text: agrichemicals

text: because it adds stability to the carbon framework; also, the relatively

text: small size

text: of fluorine is convenient as fluorine acts as an approximate

text: bioisostere

text: of the

text: hydroxyl

text: group. Introducing the carbon–fluorine bond to organic compounds is the major challenge for medicinal chemists using organofluorine chemistry, as the carbon–fluorine bond increases the probability of having a successful drug by about a factor of ten. An estimated 20% of pharmaceuticals, and 30–40% of agrichemicals are organofluorines, including several of the top drugs. Examples include

text: fluoxetine

text: (Prozac),

text: paroxetine

text: (Paxil),

text: ciprofloxacin

text: (Cipro),

text: mefloquine

text: , and

text: fluconazole

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answers: 40% of agrichemicals

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answers: about a factor of ten

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answers: The most common example is fluoroacetate

text: Factors affecting the rate of olefin insertions include the formation of the cyclic, planar, four-center transition state involving incipient formation of a bond between the metal and an olefin carbon. From this transition state, it can be seen that a partial positive charge forms on the β-carbon with a partial negative charge formed on the carbon initially bonded to the metal. This polarization explains the subsequently observed formation of the bond between the negatively charged carbon/hydrogen and the positively charged β-carbon as well as the simultaneous formation of the metal-α-carbon bond. This transition state also highlights the two factors that most strongly contribute to the rate of olefin insertion reactions: (i) orbital overlap of the alkyl group initially attached to the metal and (ii) the strength of the metal-alkyl bond. With greater orbital overlap between the partially positive β-carbon and the partially negative hydrogen/alkyl group carbon, the formation of the new C-C bond is facilitated. With increasing strength of the metal-alkyl bond, the breaking of the bond between the metal and the hydrogen/alkyl carbon bond to form the two new bonds with the α-carbon and β-carbon (respectively) is slower, thus decreasing the rate of the insertion reaction.

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answers: -carbon

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text: Salvador et al.  reported an isotypic terbium compoundTbCSi(B). Most parts of the crystal structure are the same as those described above; however, its bonding configuration is deduced as (B)≡C-C≡(B) instead of (B)≡Si-C≡(B). The authors intentionally added carbon to grow single crystals whereas the previous crystals were accidentally contaminated by carbon during their growth. Thus, higher carbon concentration was achieved. Existence of both bonding schemes of (B)≡Si-C≡(B) and (B)≡C-C≡(B) suggests the occpancy of the carbon sites of 50–100%. On the other hand, (B)≡Si-Si≡(B) bonding scheme is unlikely because of too short Si-Si distance, suggesting that the minimum carbon occupancy at the site is 50%. Some B atoms may replace C atoms at the C3 site, as previously assigned to the B site. However, the carbon occupation is more likely because the site is tetrahedrally coordinated whereas the B occupation of the site needs an extra electron to complete tetrahedral bonding. Thus, carbon is indispensable for this group of compounds.

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answers: 2: The answer has limited relevance and completeness, with significant gaps or inaccuracies.

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answers: It is impossible to say

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answers: 50–100%

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answers: Hydrocarbons

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answers: Carbon is indispensable for this group of compounds

text: Further evidence that the assignment of the so-called "valence hole" should be to the S units in these two formulae is the length of the S-S bonds, which are significantly shorter in CuS (0.207 nm) and CuS (0.203 nm) than in the "classical" disulfide Fe(S) (0.218 nm). This bond length difference has been ascribed to the higher bond order in (S-S) compared to (S-S) due to electrons being removed from a π* antibonding orbital. NMR studies on CuS show that there are two distinct species of copper atom, one with a more metallic nature than the other. and this apparent discrepancy with the X-ray photo-electron spectrum data simply highlights the problem that NMR has in assigning oxidation states in a mixed-valence compound. The issue of the valence of copper in sulfides (as well as selenides and tellurides) continues to be revisited in the literature. A good example is a 2009 study of the ternary compound CuCoS<ref>Electronic environments in carrollite, CuCo2S4, determined by soft X-ray photoelectron and absorption spectroscopy<br> Alan N. Buckleya, , William M. Skinnerb, Sarah L. Harmerb, Allan Pringc and Liang-Jen Fand

text: Further evidence that the assignment of the so-called "valence hole" should be to the S units in these two formulae is the length of the S-S bonds, which are significantly shorter in CuS (0.207 nm) and CuS (0.203 nm) than in the "classical" disulfide Fe(S) (0.218 nm). This bond length difference has been ascribed to the higher bond order in (S-S) compared to (S-S) due to electrons being removed from a π*

text: antibonding

text: orbital. NMR studies on CuS show that there are two distinct species of copper atom, one with a more metallic nature than the other. and this apparent discrepancy with the X-ray photo-electron spectrum data simply highlights the problem that NMR has in assigning oxidation states in a

text: mixed-valence

text: compound. The issue of the valence of copper in sulfides (as well as selenides and tellurides) continues to be revisited in the literature. A good example is a 2009 study of the ternary compound CuCoS<ref>Electronic environments in carrollite, CuCo2S4, determined by soft X-ray photoelectron and absorption spectroscopy<br> Alan N. Buckleya, , William M. Skinnerb, Sarah L. Harmerb, Allan Pringc and Liang-Jen Fand

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text: Interpretation of carbon isotope effects are usually complicated by simultaneously forming and breaking bonds to carbon. Even reactions that involve only bond cleavage from the carbon, such as S1 reactions, involve strengthening of the remaining bonds to carbon. In many such reactions, leaving group isotope effects tend to be easier to interpret. For example, substitution and elimination reactions in which chlorine act as a leaving group are convenient to interpret, especially since chlorine acts as a monatomic species with no internal bonding to complicate the reaction coordinate, and it has two stable isotopes, Cl and Cl, both with high abundance. The major challenge to the interpretation of such isotope affects is the solvation of the leaving group.

text: Interpretation of carbon isotope effects are usually complicated by simultaneously forming and breaking bonds to carbon. Even reactions that involve only bond cleavage from the carbon, such as S1 reactions, involve strengthening of the remaining bonds to carbon. In many such reactions, leaving group isotope effects tend to be easier to interpret. For example, substitution and elimination reactions in which chlorine act as a leaving group are convenient to interpret, especially since chlorine acts as a monatomic species with no internal bonding to complicate the reaction coordinate, and it has two stable isotopes, Cl and Cl, both with high abundance. The major challenge to the interpretation of such isotope affects is the solvation of the leaving group.

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answers: It has two stable isotopes

text: is the bond length experimentally measured, and b is a constant, depending on the atoms. Pauling suggested a value of 0.353 Å for b, for carbon-carbon bonds in the original equation:

text: is the bond length experimentally measured, and b is a constant, depending on the atoms. Pauling suggested a value of 0.353 Å for b, for carbon-carbon bonds in the original equation:

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answers: 0.353

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text: The ground state is believed to be a bent triplet, with two orthogonal sp hybrid orbitals singly occupied by unpaired spins. One electron occupies an orbital of sigma symmetry in the plane of the rings, while the other occupies an orbital of pi symmetry, which interacts with the pi systems of the adjacent aromatic rings (delocalization into the rings is minimal, since zero-field parameter D is high). The zero field splitting parameters predict a bond angle greater than 135°, and since the ideal bond geometry for cyclopentane carbons is about 109°, considerable ring strain causes the methylene sigma bonds to be bent. In the singlet state, the spin-paired electrons occupy the sp hybrid orbital, orthogonal to an empty p-orbital. Conversion of singlet to triplet fluorenylidene is achieved through intersystem crossing (ISC).

text: The ground state is believed to be a bent triplet, with two orthogonal sp

text: hybrid orbitals

text: singly occupied by unpaired spins. One electron occupies an orbital of sigma symmetry in the plane of the rings, while the other occupies an orbital of pi symmetry, which interacts with the pi systems of the adjacent aromatic rings (delocalization into the rings is minimal, since zero-field parameter D is high). The

text: zero field splitting

text: parameters predict a bond angle greater than 135°, and since the ideal bond geometry for cyclopentane carbons is about 109°, considerable ring strain causes the methylene sigma bonds to be bent. In the singlet state, the spin-paired electrons occupy the sp hybrid orbital, orthogonal to an empty p-orbital. Conversion of singlet to triplet fluorenylidene is achieved through intersystem crossing (ISC).

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text: Discoveries in organometallic chemistry have led to important insights into chemical bonding. Zeise's salt, K[PtCl(CH)]·HO, was reported in 1831 and Mond's discovery of Ni(CO) occurred in 1888. Each contained a bond between a metal centre and small molecule, ethylene in the case of Zeise's salt and carbon monoxide in the case of nickel tetracarbonyl. The space-filling model of the anion of Zeise's salt (image at left) shows direct bonding between the platinum metal centre (shown in blue) and the carbon atoms (shown in black) of the ethylene ligand; such metal–carbon bonds are the defining characteristic of organometallic species. Bonding models were unable to explain the nature of such metal–alkene bonds until the Dewar-Chatt-Duncanson model was proposed in the 1950s. The original formulation covered only metal–alkene bonds but the model was expanded over time to cover systems like metal carbonyls (including [Ni(CO)]) where π backbonding is important.

text: Discoveries in

text: organometallic chemistry

text: have led to important insights into

text: chemical bonding

text: Zeise's salt

text: , K[PtCl(CH)]·HO, was reported in 1831 and

text: Mond's

text: discovery of Ni(CO) occurred in 1888. Each contained a bond between a metal centre and small molecule,

text: ethylene

text: in the case of Zeise's salt and

text: carbon monoxide

text: in the case of

text: nickel tetracarbonyl

text: . The

text: space-filling model

text: of the anion of Zeise's salt (image at left) shows direct bonding between the

text: platinum

text: metal centre (shown in blue) and the carbon atoms (shown in black) of the ethylene

text: ligand

text: ; such metal–carbon bonds are the defining characteristic of

text: organometallic species

text: . Bonding models were unable to explain the nature of such metal–alkene bonds until the

text: Dewar-Chatt-Duncanson model

text: was proposed in the 1950s. The original formulation covered only metal–alkene bonds but the model was expanded over time to cover systems like

text: metal carbonyl

text: s (including [Ni(CO)]) where

text: π backbonding

text: is important.

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answers: [Ni(CO)]

text: Prismane is a colourless liquid at room temperature.  The deviation of the carbon-carbon bond angle from 109° to 60° in a triangle leads to a high ring strain, reminiscent of that of cyclopropane but greater. The compound is explosive, which is unusual for a hydrocarbon. Due to this ring strain, the bonds have a low bond energy and break at a low activation energy, which makes synthesis of the molecule difficult; Woodward and Hoffmann noted that prismane's thermal rearrangement to benzene is symmetry-forbidden, comparing it to "an angry tiger unable to break out of a paper cage."

text: Prismane is a colourless liquid at room temperature.  The deviation of the carbon-carbon bond angle from 109° to 60° in a

text: triangle

text: leads to a high

text: ring strain

text: , reminiscent of that of

text: cyclopropane

text: but greater. The compound is explosive, which is unusual for a hydrocarbon. Due to this ring strain, the bonds have a low bond energy and break at a low

text: activation energy

text: , which makes synthesis of the molecule difficult; Woodward and Hoffmann noted that prismane's thermal rearrangement to benzene is

text: symmetry-forbidden

text: , comparing it to "an angry tiger unable to break out of a paper cage."

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text: A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two. The most common double bond, that is between two carbon atoms, can be found in alkenes. Many types of double bonds exist between two different elements. For example, in a carbonyl group with a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N) and sulfoxides (S=O). In skeletal formula the double bond is drawn as two parallel lines (=) between the two connected atoms; typographically, the equals sign is used for this. Double bonds were first introduced in chemical notation by prominent Russian chemist Alexander Butlerov.

text: A double bond in

text: chemistry

text: is a

text: chemical bond

text: between two

text: chemical element

text: s involving four

text: bonding electron

text: s instead of the usual two. The most common double bond, that is between two carbon atoms, can be found in

text: alkene

text: s. Many types of double bonds exist between two different elements. For example, in a

text: carbonyl

text: group with a carbon atom and an oxygen atom. Other common double bonds are found in

text: azo compound

text: s (N=N),

text: imine

text: s (C=N) and

text: sulfoxide

text: s (S=O). In

text: skeletal formula

text: the double bond is drawn as two parallel lines (=) between the two connected atoms; typographically, the

text: equals sign

text: is used for this. Double bonds were first introduced in chemical notation by prominent

text: Russia

text: n chemist

text: Alexander Butlerov

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answers: alkenes

text: The formation of a carbon–carbon bond is a key step in the biosynthetic pathways by which fatty acids and polyketide are made. The thiolase superfamily enzymes catalyse the carbon–carbon-bond formation via a thioester-dependent Claisen condensation reaction mechanism.

text: The formation of a carbon–carbon bond is a key step in the biosynthetic pathways by which

text: fatty acids

text: and

text: polyketide

text: are made. The thiolase superfamily

text: enzymes

text: catalyse the carbon–carbon-bond formation via a thioester-dependent

text: Claisen condensation

text: reaction mechanism.

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answers: carbon–carbon bond

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answers: carbon–carbon

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answers: polyketide

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answers: carbon–carbon bond

text: Carbon monoxide consists of one carbon atom and one oxygen atom, connected by a triple bond that consists of two covalent bonds as well as one dative covalent bond. It is the simplest oxocarbon and is isoelectronic with the cyanide anion, the nitrosonium cation and molecular nitrogen. In coordination complexes the carbon monoxide ligand is called carbonyl.

text: Carbon monoxide consists of one

text: carbon

text: atom and one

text: oxygen

text: atom, connected by a

text: triple bond

text: that consists of two

text: covalent bond

text: s as well as one

text: dative

text: covalent bond. It is the simplest

text: oxocarbon

text: and is

text: isoelectronic

text: with the

text: cyanide

text: anion, the

text: nitrosonium

text: cation and molecular

text: nitrogen

text: . In

text: coordination complex

text: es the carbon monoxide

text: ligand

text: is called

text: carbonyl

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answers: carbonyl

text: Unlike benzene, the carbon–carbon bonds in naphthalene are not of the same length. The bonds C1−C2, C3−C4, C5−C6 and C7−C8 are about 1.37 Å (137 pm) in length, whereas the other carbon–carbon bonds are about 1.42 Å (142 pm) long. This difference, established by X-ray diffraction, is consistent with the valence bond model in naphthalene and in particular, with the theorem of cross-conjugation. This theorem would describe naphthalene as an aromatic benzene unit bonded to a diene but not extensively conjugated to it (at least in the ground state). As such, naphthalene possesses several resonance structures.

text: Unlike

text: benzene

text: , the carbon–carbon bonds in naphthalene are not of the same length. The bonds C1−C2, C3−C4, C5−C6 and C7−C8 are about 1.37 Å (137 pm) in length, whereas the other carbon–carbon bonds are about 1.42 Å (142 pm) long. This difference, established by

text: X-ray diffraction

text: , is consistent with the

text: valence bond

text: model in naphthalene and in particular, with the theorem of

text: cross-conjugation

text: . This theorem would describe naphthalene as an

text: aromatic

text: benzene unit bonded to a

text: diene

text: but not extensively

text: conjugated

text: to it (at least in the

text: ground state

text: ). As such, naphthalene possesses several

text: resonance

text: structures.

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answers: 1.42  (142 pm)

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answers: Methane

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answers: C5 C6 and C7 C8

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answers: benzene

text: In organic chemistry, a nucleophilic addition reaction is an addition reaction where a chemical compound with an electron-deficient or electrophilic double or triple bond, a π bond, reacts with electron-rich reactant, termed a nucleophile, with disappearance of the double bond and creation of two new single, or σ, bonds. The reactions are involved in the biological synthesis of compounds in the metabolism of every living organism, and are used by chemists in academia and industries such as pharmaceuticals to prepare most new complex organic chemicals, and so are central to organic chemistry. Addition reactions require the presence of groups with multiple bonds in the electrophile: carbon–heteroatom multiple bonds as in carbonyls, imines, and nitriles, or carbon–carbon double or triple bonds.

text: In

text: organic chemistry

text: , a nucleophilic addition reaction is an

text: addition reaction

text: where a

text: chemical compound

text: with an

text: electron-deficient

text: or

text: electrophilic

text: double

text: or

text: triple bond

text: , a

text: π bond

text: , reacts with electron-rich reactant, termed a

text: nucleophile

text: , with disappearance of the double bond and creation of two new

text: single

text: , or

text: σ

text: , bonds. The reactions are involved in the

text: biological synthesis

text: of compounds in the

text: metabolism

text: of every living

text: organism

text: , and are used by chemists in academia and industries such as

text: pharmaceuticals

text: to prepare most new complex

text: organic chemical

text: s, and so are central to organic chemistry. Addition reactions require the presence of groups with multiple bonds in the electrophile: carbon–

text: heteroatom

text: multiple bonds as in

text: carbonyl

text: s,

text: imine

text: s, and

text: nitrile

text: s, or carbon–carbon double or triple bonds.

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answers: carbonyls

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answers: carbonyls, imines, and nitriles

text: Perfluoroalkanes are very stable because of the strength of the carbon–fluorine bond, one of the strongest in organic chemistry. Its strength is a result of the electronegativity of fluorine imparting partial ionic character through partial charges on the carbon and fluorine atoms, which shorten and strengthen the bond through favorable covalent interactions. Additionally, multiple carbon–fluorine bonds increase the strength and stability of other nearby carbon–fluorine bonds on the same geminal carbon, as the carbon has a higher positive partial charge. Furthermore, multiple carbon–fluorine bonds also strengthen the "skeletal" carbon–carbon bonds from the inductive effect. Therefore, saturated fluorocarbons are more chemically and thermally stable than their corresponding hydrocarbon counterparts, and indeed any other organic compound. They are susceptible to attack by very strong reductants, e.g., Birch reduction and very specialized organometallic complexes.

text: Perfluoroalkanes are very stable because of the strength of the

text: carbon–fluorine bond

text: , one of the strongest in organic chemistry. Its strength is a result of the electronegativity of fluorine imparting partial ionic character through

text: partial charge

text: s on the carbon and fluorine atoms, which shorten and strengthen the bond through favorable

text: covalent

text: interactions. Additionally, multiple carbon–fluorine bonds increase the strength and stability of other nearby carbon–fluorine bonds on the same

text: geminal

text: carbon, as the carbon has a higher positive partial charge. Furthermore, multiple carbon–fluorine bonds also strengthen the "skeletal" carbon–carbon bonds from the

text: inductive effect

text: . Therefore,

text: saturated

text: fluorocarbons are more chemically and thermally stable than their corresponding hydrocarbon counterparts, and indeed any other organic compound. They are susceptible to attack by very strong reductants, e.g.,

text: Birch reduction

text: and very specialized organometallic complexes.

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answers: Perfluoroalkanes

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answers: perfluoroalkanes

text: Most metals form coordination complexes containing covalently attached carbon monoxide. Only metals in lower oxidation states will complex with carbon monoxide ligands. This is because there must be sufficient electron density to facilitate back-donation from the metal d-orbital, to the π*molecular orbital from CO. The lone pair on the carbon atom in CO, also donates electron density to the d on the metal to form a sigma bond. This electron donation is also exhibited with the cis effect, or the labilization of CO ligands in the cis position. Nickel carbonyl, for example, forms by the direct combination of carbon monoxide and nickel metal:

text: Most metals form

text: coordination complex

text: es containing covalently attached carbon monoxide. Only metals in lower oxidation states will complex with carbon monoxide

text: ligands

text: . This is because there must be sufficient electron density to facilitate

text: back-donation

text: from the metal d-orbital, to the π*

text: molecular orbital

text: from CO. The lone pair on the carbon atom in CO, also donates electron density to the d on the metal to form a

text: sigma bond

text: . This electron donation is also exhibited with the

text: cis effect

text: , or the labilization of CO ligands in the cis position.

text: Nickel carbonyl

text: , for example, forms by the direct combination of carbon monoxide and

text: nickel

text: metal:

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answers: Most metals

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answers: carbonyl

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answers: NDQ_016401

answers: Carbon monoxide

text: AlO commonly exists as a gas, since the solid state is not stable at room temperature and is only stable between 1050 and 1600 °C.  Aluminium (I) Oxide is formed by heating Al and AlO in vacuo while in the presence of SiO and C, and only by condensing the products.  Information is not commonly available on this compound due to instability, complex high-temperature spectra, difficult detection, and identification.  In reduction, AlO is a major component of vapors of AlO.  There are also 12 valence electrons in AlO.  AlO molecules can be detected by mass spectrometry, infrared emission, and ultraviolet absorption and emission in the gas phase.  The molecule is linear at equilibrium in the ground state. In term of valence bond theory, these molecules can be described as adopting sp orbital hybridisation, featuring one sigma and two pi bonds. The corresponding ground state for the valence electrons is 1σ 1σ* 2σ 1π 1π*, where the 1σ and 1σ* orbitals cancel, and the 1π and 1π* partially cancel. The overall configuration yields a divalent triplet molecule, with one lone electron focused on the oxygen atom and the other focused equally between the aluminium atoms.

text: AlO commonly exists as a gas, since the solid state is not stable at room temperature and is only stable between 1050 and 1600 °C.  Aluminium (I) Oxide is formed by heating Al and AlO in vacuo while in the presence of SiO and C, and only by condensing the products.  Information is not commonly available on this compound due to instability, complex high-temperature spectra, difficult detection, and identification.  In reduction, AlO is a major component of vapors of AlO.  There are also 12 valence electrons in AlO.  AlO molecules can be detected by

text: mass spectrometry

text: infrared

text: emission, and

text: ultraviolet

text: absorption and emission in the gas phase.  The molecule is linear at equilibrium in the

text: ground state

text: . In term of valence bond theory, these molecules can be described as adopting sp

text: orbital hybridisation

text: , featuring one sigma and two pi bonds. The corresponding ground state for the valence electrons is 1σ 1σ* 2σ 1π 1π*, where the 1σ and 1σ* orbitals cancel, and the 1π and 1π* partially cancel. The overall configuration yields a divalent triplet molecule, with one lone electron focused on the oxygen atom and the other focused equally between the aluminium atoms.

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answers: AlO

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answers: 12 valence electrons

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answers: carbon

text: A Sawhorse representation, on the other hand, views a carbon-carbon bond from an oblique angle. This type of representation makes it easy to visualize the molecule as a whole in 3-D.

text: A Sawhorse representation, on the other hand, views a carbon-carbon bond from an oblique angle. This type of representation makes it easy to visualize the molecule as a whole in 3-D.

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answers: carbon-carbon bond

text: Carbon atoms with unsatisfied bonds are found in some oxides, such as the diradical CO or :C=C=O; but these compounds are generally too reactive to be isolated in bulk.  Loss or gain of electrons can result in monovalent negative oxygen (-), trivalent positive oxygen (≡), or trivalent negative carbon (≡). The last two are found in carbon monoxide, C≡O.  Negative oxygen occurs in most oxocarbon anions.

text: Carbon atoms with unsatisfied bonds are found in some oxides, such as the diradical CO or :C=C=O; but these compounds are generally too reactive to be isolated in bulk.  Loss or gain of electrons can result in monovalent negative oxygen (-), trivalent positive oxygen (≡), or trivalent negative carbon (≡). The last two are found in carbon monoxide, C≡O.  Negative oxygen occurs in most

text: oxocarbon anion

text: s.

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answers: Carbon atoms

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answers: Oxygen

text: The covalent (sharing) aspect of the bonding is overemphasized in the use of formal charges, since in reality there is a higher electron density around the oxygen atoms due to their higher electronegativity compared to the carbon atom.   This can be most effectively visualized in an electrostatic potential map.

text: The covalent (sharing) aspect of the bonding is overemphasized in the use of formal charges, since in reality there is a higher electron density around the oxygen atoms due to their higher electronegativity compared to the carbon atom.   This can be most effectively visualized in an

text: electrostatic potential map

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answers: covalent

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answers: covalent

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answers: Oxygen

text: The single bonds are formed from overlap of hybridized atomic sp-orbitals in line between the carbon nuclei—these are called σ-bonds. Double bonds consist of a σ-bond and a π-bond. The π-bonds are formed from overlap of atomic p-orbitals above and below the plane of the ring. The following diagram shows the positions of these p-orbitals:

text: The single bonds are formed from overlap of hybridized

text: atomic sp-orbitals

text: in line between the carbon nuclei—these are called

text: σ-bonds

text: . Double bonds consist of a σ-bond and a π-bond. The π-bonds are formed from overlap of

text: atomic p-orbitals

text: above and below the plane of the ring. The following diagram shows the positions of these p-orbitals:

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answers: 3: The answer has limited relevance and completeness, with noticeable gaps or inaccuracies.

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answers: carbon nuclei

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answers: single bonds

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answers: Hydrocarbons

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answers: -bonds

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answers: two

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answers: carbon nuclei

text: Octatetraene is a class of organic chemical compound. Ideally octatetraenes are linear alkenes with backbones eight carbon atoms in length and with four double carbon-carbon bonds and three single bonds. Because aliphatic carbon is tetravalent, this leaves ten bonds by which hydrogen atoms can attach to the carbon skeleton.

text: Octatetraene is a class of organic chemical compound. Ideally octatetraenes are linear

text: alkene

text: s with backbones eight carbon atoms in length and with four double carbon-carbon bonds and three single bonds. Because

text: aliphatic

text: carbon is tetravalent, this leaves ten bonds by which hydrogen atoms can attach to the carbon skeleton.

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answers: aliphatic carbon

text: Ionic crystals may contain a mixture of covalent and ionic species, as for example salts of complex acids, such as sodium cyanide, NaCN. X-ray diffraction shows that in NaCN, for example, the bonds between sodium cations (Na) and the cyanide anions (CN) are ionic, with no sodium ion associated with any particular cyanide. However, the bonds between C and N atoms in cyanide are of the covalent type, making each of the carbon and nitrogen associated with just one of its opposite type, to which it is physically much closer than it is to other carbons or nitrogens in a sodium cyanide crystal.

text: Ionic crystals may contain a mixture of covalent and ionic species, as for example salts of complex acids, such as sodium cyanide, NaCN. X-ray diffraction shows that in NaCN, for example, the bonds between sodium

text: cation

text: s (Na) and the cyanide

text: anion

text: s (CN) are ionic, with no sodium ion associated with any particular cyanide. However, the bonds between C and N atoms in cyanide are of the covalent type, making each of the carbon and nitrogen associated with just one of its opposite type, to which it is physically much closer than it is to other carbons or nitrogens in a sodium cyanide crystal.

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text: The carbon-silicon bond is highly electron-releasing and can stabilize a positive charge in the β position through hyperconjugation. Electrophilic additions to allyl- and vinylsilanes take advantage of this, and site selectivity generally reflects this property—electrophiles become bound to the carbon γ to the silyl group. The electron-donating strength of the carbon-silicon bond is similar to that of an acetamide substituent and equal to roughly two alkyl groups. After formation of the carbon-electrophile bond, silicon elimination is assisted by a nucleophile.

text: The carbon-silicon bond is highly electron-releasing and can stabilize a positive charge in the β position through hyperconjugation. Electrophilic additions to allyl- and vinylsilanes take advantage of this, and site selectivity generally reflects this property—electrophiles become bound to the carbon γ to the silyl group. The electron-donating strength of the carbon-silicon bond is similar to that of an acetamide substituent and equal to roughly two alkyl groups. After formation of the carbon-electrophile bond, silicon elimination is assisted by a nucleophile.

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answers: The carbon-silicon bond

answers: NDQ_016396

answers: two alkyl groups

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answers: hydrocarbon

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answers: silyl group

answers: NDQ_016400

answers: roughly two alkyl groups

answers: NDQ_016401

answers: It can form more compounds than any other element

text: A table with experimental single bonds for carbon to other elements is given below. Bond lengths are given in picometers. By approximation the bond distance between two different atoms is the sum of the individual covalent radii (these are given in the chemical element articles for each element). As a general trend, bond distances decrease across the row in the periodic table and increase down a group. This trend is identical to that of the atomic radius.

text: A table with experimental

text: single bond

text: s for carbon to other elements is given below. Bond lengths are given in

text: picometer

text: s. By approximation the bond distance between two different atoms is the sum of the individual

text: covalent radii

text: (these are given in the

text: chemical element

text: articles for each element). As a general trend, bond distances decrease across the row in the

text: periodic table

text: and increase down a group. This trend is identical to that of the

text: atomic radius

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text: "What we normally think of as 'life' is based on chains of carbon atoms, with a few other atoms, such as nitrogen or phosphorus", per Stephen Hawking in a 2008 lecture, "carbon [...] has the richest chemistry."  The most important characteristics of carbon as a basis for the chemistry of life are, that it has four valence bonds, and that the energy required to make or break a bond is at an appropriate level for building molecules, which are stable and reactive. Carbon atoms bond readily to other carbon atoms; this allows the building of arbitrarily long complex molecules and polymers.

text: "What we normally think of as 'life' is based on chains of carbon atoms, with a few other atoms, such as nitrogen or phosphorus", per Stephen Hawking in a 2008 lecture, "carbon [...] has the richest chemistry."  The most important characteristics of carbon as a basis for the

text: chemistry

text: of life are, that it has four valence bonds, and that the energy required to make or break a bond is at an appropriate level for building molecules, which are stable and reactive. Carbon atoms bond readily to other carbon atoms; this allows the building of arbitrarily long complex molecules and

text: polymers

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answers: This allows the building of arbitrarily long complex molecules and polymers

text: In 1856 Kekulé became Privatdozent at the University of Heidelberg.  In 1858 he was hired as full professor at the University of Ghent, then in 1867 he was called to Bonn, where he remained for the rest of his career.  Basing his ideas on those of predecessors such as Williamson, Edward Frankland, William Odling, Auguste Laurent, Charles-Adolphe Wurtz and others, Kekulé was the principal formulator of the theory of chemical structure (1857–58). This theory proceeds from the idea of atomic valence, especially the tetravalence of carbon (which Kekulé announced late in 1857) and the ability of carbon atoms to link to each other (announced in a paper published in May 1858), to the determination of the bonding order of all of the atoms in a molecule. Archibald Scott Couper independently arrived at the idea of self-linking of carbon atoms (his paper appeared in June 1858), and provided the first molecular formulas where lines symbolize bonds connecting the atoms. For organic chemists, the theory of structure provided dramatic new clarity of understanding, and a reliable guide to both analytic and especially synthetic work. As a consequence, the field of organic chemistry developed explosively from this point. Among those who were most active in pursuing early structural investigations were, in addition to Kekulé and Couper, Frankland, Wurtz, Alexander Crum Brown, Emil Erlenmeyer, and Alexander Butlerov.

text: In 1856 Kekulé became

text: Privatdozent

text: at the

text: University of Heidelberg

text: .  In 1858 he was hired as full professor at the

text: University of Ghent

text: , then in 1867 he was called to

text: Bonn

text: , where he remained for the rest of his career.  Basing his ideas on those of predecessors such as Williamson,

text: Edward Frankland

text: William Odling

text: Auguste Laurent

text: Charles-Adolphe Wurtz

text: and others, Kekulé was the principal formulator of the theory of chemical structure (1857–58). This theory proceeds from the idea of atomic valence, especially the

text: tetravalence

text: of carbon (which Kekulé announced late in 1857) and the ability of carbon atoms to link to each other (announced in a paper published in May 1858), to the determination of the bonding order of all of the atoms in a molecule.

text: Archibald Scott Couper

text: independently arrived at the idea of self-linking of carbon atoms (his paper appeared in June 1858), and provided the first molecular formulas where lines symbolize bonds connecting the atoms. For organic chemists, the theory of structure provided dramatic new clarity of understanding, and a reliable guide to both analytic and especially synthetic work. As a consequence, the field of organic chemistry developed explosively from this point. Among those who were most active in pursuing early structural investigations were, in addition to Kekulé and Couper,

text: Frankland

text: Wurtz

text: Alexander Crum Brown

text: Emil Erlenmeyer

text: , and

text: Alexander Butlerov

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answers: Tetravalent

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answers: tetravalence of carbon

text: The isomerization is a popular topic in schools.  Maleic acid and fumaric acid do not spontaneously interconvert because rotation around a carbon carbon double bond is not energetically favourable. However, conversion of the cis isomer into the trans isomer is possible by photolysis in the presence of a small amount of bromine. Light converts elemental bromine into a bromine radical, which attacks the alkene in a radical addition reaction to a bromo-alkane radical; and now single bond rotation is possible.  The bromine radicals recombine and fumaric acid is formed. In another method (used as a classroom demonstration), maleic acid is transformed into fumaric acid through the process of heating the maleic acid in hydrochloric acid solution. Reversible addition (of H) leads to free rotation about the central C-C bond and formation of the more stable and less soluble fumaric acid.

text: The

text: isomerization

text: is a popular topic in schools.  Maleic acid and fumaric acid do not spontaneously interconvert because rotation around a carbon carbon

text: double bond

text: is not energetically favourable. However, conversion of the cis isomer into the trans isomer is possible by

text: photolysis

text: in the presence of a small amount of

text: bromine

text: . Light converts elemental bromine into a bromine

text: radical

text: , which attacks the alkene in a

text: radical addition

text: reaction to a bromo-alkane radical; and now single bond rotation is possible.  The bromine radicals recombine and fumaric acid is formed. In another method (used as a classroom demonstration), maleic acid is transformed into

text: fumaric acid

text: through the process of heating the maleic acid in

text: hydrochloric acid

text: solution. Reversible addition (of H) leads to free rotation about the central C-C bond and formation of the more stable and less soluble fumaric acid.

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answers: carbon carbon double bond

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answers: double bond

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answers: Hydrocarbon

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answers: Maleic acid

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answers: carbon carbon double bond

text: Carbon and oxygen together have a total of 10 electrons in the valence shell. Following the octet rule for both carbon and oxygen, the two atoms form a triple bond, with six shared electrons in three bonding molecular orbitals, rather than the usual double bond found in organic carbonyl compounds. Since four of the shared electrons come from the oxygen atom and only two from carbon, one bonding orbital is occupied by two electrons from oxygen, forming a dative or dipolar bond. This causes a C ← O polarization of the molecule, with a small negative charge on carbon and a small positive charge on oxygen. The other two bonding orbitals are each occupied by one electron from carbon and one from oxygen, forming (polar) covalent bonds with a reverse C → O polarization, since oxygen is more electronegative than carbon. In the free carbon monoxide, a net negative charge δ- remains at the carbon end and the molecule has a small dipole moment of 0.122 D.

text: Carbon and oxygen together have a total of 10

text: electrons

text: in the

text: valence shell

text: . Following the

text: octet rule

text: for both carbon and oxygen, the two atoms form a

text: triple bond

text: , with six shared electrons in three bonding molecular orbitals, rather than the usual double bond found in organic carbonyl compounds. Since four of the shared electrons come from the oxygen atom and only two from carbon, one bonding orbital is occupied by two electrons from oxygen, forming a dative or

text: dipolar bond

text: . This causes a C ← O

text: polarization

text: of the molecule, with a small negative charge on carbon and a small positive charge on oxygen. The other two bonding orbitals are each occupied by one electron from carbon and one from oxygen, forming (polar) covalent bonds with a reverse C → O polarization, since oxygen is more

text: electronegative

text: than carbon. In the free carbon monoxide, a net negative charge δ- remains at the carbon end and the molecule has a small

text: dipole moment

text: of 0.122

text: D

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answers: carbon monoxide

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answers: six shared electrons

answers: NDQ_016401

answers: Oxygen

text: The first step in the mechanism is for FPP's carbon-carbon double bond farthest from the diphosphate group to attack the carbon adjacent to the diphosphate, forming a cyclic carbocation with the loss of the diphosphate group. A 1,3 hydride shift moves the carbocation closer to the nearest carbon-carbon double bond; the loss of a proton forms a new carbon-carbon double bond and allows the carbon-carbon double bond adjacent to the carbocation to quench this charged group, forming the byproduct germacrene D. Alternatively, the carbocation produced in the first step can immediately lose a proton to form the intermediate isolepidozene, which is subsequently attacked by water to form germacradienol. Further processing of germacradienol involves a proton-initiated cyclization and a novel retro-Prins-type fragmentation producing the intermediate octalin and byproduct acetone. Finally, protonation, a 1,2 hydride shift, and quenching by water convert octalin to geosmin.

text: The first step in the mechanism is for FPP's carbon-carbon double bond farthest from the diphosphate group to attack the carbon adjacent to the diphosphate, forming a cyclic

text: carbocation

text: with the loss of the diphosphate group. A 1,3 hydride shift moves the carbocation closer to the nearest carbon-carbon double bond; the loss of a proton forms a new carbon-carbon double bond and allows the carbon-carbon double bond adjacent to the carbocation to quench this charged group, forming the byproduct germacrene D. Alternatively, the carbocation produced in the first step can immediately lose a proton to form the intermediate

text: isolepidozene

text: , which is subsequently attacked by water to form germacradienol. Further processing of germacradienol involves a proton-initiated cyclization and a novel retro-Prins-type fragmentation producing the intermediate

text: octalin

text: and byproduct

text: acetone

text: . Finally, protonation, a 1,2 hydride shift, and quenching by water convert octalin to geosmin.

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answers: carbon

text: Citrate synthase is a member of a small family of enzymes that can directly form a carbon-carbon bond without the presence of metal ion cofactors. It catalyses the first reaction in the Krebs' cycle, namely the conversion of oxaloacetate and acetyl-coenzyme A into citrate and coenzyme A. This reaction is important for energy generation and for carbon assimilation. The reaction proceeds via a non-covalently bound citryl-coenzyme A intermediate in a 2-step process (aldol-Claisen condensation followed by the hydrolysis of citryl-CoA).

text: Citrate synthase is a member of a small family of enzymes that can directly form a carbon-carbon bond without the presence of

text: metal ion

text: cofactors

text: . It

text: catalyses

text: the first reaction in the

text: Krebs

text: ' cycle, namely the conversion of

text: oxaloacetate

text: and

text: acetyl-coenzyme A

text: into

text: citrate

text: and

text: coenzyme A

text: . This reaction is important for

text: energy

text: generation and for

text: carbon

text: assimilation. The reaction proceeds via a non-covalently bound citryl-coenzyme A

text: intermediate

text: in a 2-step process (aldol-Claisen condensation followed by the

text: hydrolysis

text: of citryl-CoA).

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answers: carbon-carbon bond

text: In diamond all four outer electrons of each carbon atom are 'localized' between the atoms in covalent bonding. The movement of electrons is restricted and diamond does not conduct an electric current. In graphite, each carbon atom uses only 3 of its 4 outer energy level electrons in covalently bonding to three other carbon atoms in a plane. Each carbon atom contributes one electron to a delocalized system of electrons that is also a part of the chemical bonding. The delocalized electrons are free to move throughout the plane. For this reason, graphite conducts electricity along the planes of carbon atoms, but does not conduct in a direction at right angles to the plane.

text: In

text: diamond

text: all four outer electrons of each

text: carbon

text: atom are 'localized' between the atoms in covalent bonding. The movement of electrons is restricted and diamond does not conduct an electric current. In

text: graphite

text: , each carbon atom uses only 3 of its 4 outer energy level electrons in covalently bonding to three other carbon atoms in a plane. Each carbon atom contributes one electron to a delocalized system of electrons that is also a part of the chemical bonding. The delocalized electrons are free to move throughout the plane. For this reason, graphite conducts electricity along the planes of carbon atoms, but does not conduct in a direction at

text: right angle

text: s to the plane.

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answers: carbon atoms

text: Valency is the combining power of an element. It is equal to number of hydrogen atoms that atom can combine or displace in forming compounds. The outermost electron shell of an atom in its uncombined state is known as the valence shell, and the electrons inthat shell are called valence electrons. The number of valence electrons determines the bondingbehavior with other atoms. Atoms tend to chemically react with each other in a manner that fills (or empties) their outer valence shells. For example, a transfer of a single electron between atoms is a useful approximation for bonds that form between atoms with one-electron more than a filled shell, and others that are one-electron short of a full shell, such as occurs in the compound sodium chloride and other chemical ionic salts. However, many elements display multiple valences, or tendencies to share differing numbers of electrons in different compounds. Thus, chemical bonding between these elements takes many forms of electron-sharing that are more than simple electron transfers. Examples include the element carbon and the organic compounds.

text: Valency is the combining power of an element. It is equal to number of hydrogen atoms that atom can combine or displace in forming compounds. The outermost electron shell of an atom in its uncombined state is known as the

text: valence shell

text: , and the electrons inthat shell are called

text: valence electron

text: s. The number of valence electrons determines the

text: bonding

text: behavior with other atoms. Atoms tend to

text: chemically react

text: with each other in a manner that fills (or empties) their outer valence shells. For example, a transfer of a single electron between atoms is a useful approximation for bonds that form between atoms with one-electron more than a filled shell, and others that are one-electron short of a full shell, such as occurs in the compound

text: sodium chloride

text: and other chemical ionic salts. However, many elements display multiple valences, or tendencies to share differing numbers of electrons in different compounds. Thus,

text: chemical bond

text: ing between these elements takes many forms of electron-sharing that are more than simple electron transfers. Examples include the element carbon and the

text: organic compounds

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answers: It is equal to number of hydrogen atoms that atom can combine or displace

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answers: Valency

text: Carbon atoms are tetravalent, forming four covalent bonds with other atoms, whereas hydrogen atoms bond with only one other atom. In saturated fatty acids, each carbon atom (besides the last) is connected to its two neighbour carbon atoms as well as two hydrogen atoms. In unsaturated fatty acids, the carbon atoms that are missing a hydrogen atom are joined by double bonds rather than single bonds so that each carbon atom participates in four bonds.

text: Carbon atoms are

text: tetravalent

text: , forming four

text: covalent bond

text: s with other atoms, whereas hydrogen atoms bond with only one other atom. In saturated fatty acids, each carbon atom (besides the last) is connected to its two neighbour carbon atoms as well as two hydrogen atoms. In unsaturated fatty acids, the carbon atoms that are missing a hydrogen atom are joined by double bonds rather than single bonds so that each carbon atom participates in four bonds.

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answers: In unsaturated fatty acids

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answers: tetravalent

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answers: Carbon atoms are tetravalent

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answers: unsaturated fatty acids

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answers: Carbon atoms are tetravalent

text: In organic molecules scintillation is a product of π-orbitals.  Organic materials form molecular crystals where the molecules are loosely bound by Van der Waals forces.  The ground state of C is 1s 2s 2p.  In valence bond theory, when carbon forms compounds, one of the 2s electrons is excited into the 2p state resulting in a configuration of 1s 2s 2p.  To describe the different valencies of carbon, the four valence electron orbitals, one 2s and three 2p, are considered to be mixed or hybridized in several alternative configurations.  For example, in a tetrahedral configuration the s and p orbitals combine to produce four hybrid orbitals.   In another configuration, known as trigonal configuration, one of the p-orbitals (say p) remains unchanged and three hybrid orbitals are produced by mixing the s, p and p orbitals.  The orbitals that are symmetrical about the bonding axes and plane of the molecule (sp) are known as σ-electrons and the bonds are called σ-bonds.  The p orbital is called a π-orbital.  A π-bond occurs when two π-orbitals interact.  This occurs when their nodal planes are coplanar.

text: In organic molecules scintillation is a product of

text: π-orbitals

text: .  Organic materials form molecular crystals where the molecules are loosely bound by

text: Van der Waals force

text: s.  The ground state of C is 1s 2s 2p.  In valence bond theory, when carbon forms compounds, one of the 2s electrons is excited into the 2p state resulting in a configuration of 1s 2s 2p.  To describe the different valencies of carbon, the four valence electron orbitals, one 2s and three 2p, are considered to be mixed or hybridized in several alternative configurations.  For example, in a tetrahedral configuration the s and p orbitals combine to produce four hybrid orbitals.   In another configuration, known as trigonal configuration, one of the p-orbitals (say p) remains unchanged and three hybrid orbitals are produced by mixing the s, p and p orbitals.  The orbitals that are symmetrical about the bonding axes and plane of the molecule (sp) are known as σ-electrons and the bonds are called σ-bonds.  The p orbital is called a π-orbital.  A π-bond occurs when two π-orbitals interact.  This occurs when their nodal planes are coplanar.

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answers: The ground state of C

text: Historic interest in benzene arose from the uncertainty over its structure and reactivity.  It was well established that it had a carbon to hydrogen ratio of 1:1 which suggested the presence of double or triple bond carbon-to-carbon bonds, yet such unsaturated compounds typically undergo addition reactions, which benzene does not.  Numerous potential structures were proposed, including by Claus, Dewar, Ladenburg, Armstrong, and Thiele.  The most influential proposal was that of Kekulé who in 1865 suggested a cyclic structure of six carbon atoms with alternating single and double bonds  Kekulé based his argument on the now well-known observations of arene substitution patterns, namely that there are always only one isomer of any monoderivative of benzene and three isomers of every disubstituted derivative.  Critics noted that Kekulé's proposal implied that there should be two distinguishable isomers for an ortho-substitution (a 1,2-disubstituion) depending on whether a single or double bond joined these two carbons.  Kekulé suggested in reply that benzene had two complementary structures and that these forms rapidly interconverted, which would also explain the lack of addition reactions (as the valency of each carbon atom is not that expected of a double bond).  Though this interconversion is incorrect —in fact, they are both resonance contributors to the actual structure (which is closest to Thiele's structure)— the geometry and structure proposed by Kekulé are correct.  Benzene is the prototypical example of an aromatic compound, a hitherto unknown class of compounds, and its synthesis was the first example of aromatization, the process and chemical reactions whereby an aromatic system is formed.  The new understanding of benzene and all aromatic compounds was so important for both pure and applied chemistry that in 1890 the German Chemical Society organized an elaborate appreciation in Kekulé's honor, celebrating the twenty-fifth anniversary of his first benzene paper; its 150th anniversary was also marked.  The cyclic nature of benzene was confirmed crystallographically by Kathleen Lonsdale in 1929.

text: Historic interest in benzene arose from the uncertainty over its structure and reactivity.  It was well established that it had a carbon to hydrogen ratio of 1:1 which suggested the presence of

text: double

text: or

text: triple bond

text: carbon-to-carbon bonds, yet such

text: unsaturated compounds

text: typically undergo

text: addition reaction

text: s, which benzene does not.  Numerous potential structures were proposed, including by

text: Claus

text: Dewar

text: Ladenburg

text: Armstrong

text: , and

text: Thiele

text: .  The most influential proposal was that of

text: Kekulé

text: who in 1865 suggested a cyclic structure of six carbon atoms with alternating single and double bonds  Kekulé based his argument on the now well-known observations of

text: arene substitution patterns

text: , namely that there are always only one

text: isomer

text: of any

text: monoderivative

text: of benzene and three isomers of every disubstituted derivative.  Critics noted that Kekulé's proposal implied that there should be two distinguishable isomers for an ortho-substitution (a 1,2-disubstituion) depending on whether a single or double bond joined these two carbons.  Kekulé suggested in reply that benzene had two complementary structures and that these forms rapidly interconverted, which would also explain the lack of addition reactions (as the valency of each carbon atom is not that expected of a double bond).  Though this interconversion is incorrect —in fact, they are both

text: resonance contributors

text: to the actual structure (which is closest to Thiele's structure)— the geometry and structure proposed by Kekulé are correct.  Benzene is the prototypical example of an aromatic compound, a hitherto unknown class of compounds, and its synthesis was the first example of aromatization, the process and chemical reactions whereby an aromatic system is formed.  The new understanding of benzene and all aromatic compounds was so important for both pure and applied chemistry that in 1890 the German Chemical Society organized an elaborate appreciation in Kekulé's honor, celebrating the twenty-fifth anniversary of his first benzene paper; its 150th anniversary was also marked.  The cyclic nature of benzene was confirmed

text: crystallographically

text: by

text: Kathleen Lonsdale

text: in 1929.

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answers: 0: The answer is not relevant or complete at all.

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answers: carbon to hydrogen ratio of 1:1

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answers: single or double

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answers: Kekulé

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answers: Kekulé's proposal implied that there should be two distinguishable isomers

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answers: carbon-to-carbon bonds

text: In 1856 Archibald Scott Couper went to work for a French chemist, Charles-Adolphe Wurtz. Whilst in Paris he came up with the idea of links between atoms that could explain how individual atoms formed compounds. He called these links bonds.  Somehow, Couper realised that carbon can form four bonds, thereby attaching itself with different strengths to other carbon atoms in a compound:

text: In 1856

text: Archibald Scott Couper

text: went to work for a French chemist,

text: Charles-Adolphe Wurtz

text: . Whilst in Paris he came up with the idea of links between atoms that could explain how individual atoms formed compounds. He called these links

text: bonds

text: .  Somehow, Couper realised that carbon can form four bonds, thereby attaching itself with different strengths to other carbon atoms in a compound:

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answers: Wurtz

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answers: NDQ_016401

answers: It can form four bonds

text: Enoyl-CoA-(∆) isomerase, also known as dodecenoyl-CoA-(∆) isomerase, 3,2-trans-enoyl-CoA isomerase, ∆3(cis),∆2(trans)-enoyl-CoA isomerase, or acetylene-allene isomerase, () is an enzyme that catalyzes the conversion of cis-or trans-double bonds of fatty acids at gamma-carbon (position 3) to trans double bonds at beta-carbon (position 2). It plays a particularly important role in the metabolism of unsaturated fatty acids.

text: Enoyl-CoA-(∆) isomerase, also known as dodecenoyl-CoA-(∆) isomerase, 3,2-trans-enoyl-CoA isomerase, ∆3(cis),∆2(trans)-enoyl-CoA isomerase, or acetylene-allene isomerase, () is an

text: enzyme

text: that catalyzes the conversion of cis-or trans-

text: double bond

text: s of

text: fatty acids

text: at gamma-

text: carbon

text: (position 3) to trans

text: double bond

text: s at beta-

text: carbon

text: (position 2). It plays a particularly important role in the

text: metabolism

text: of

text: unsaturated fatty acid

text: s.

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answers: NDQ_016399

answers: gamma-carbon

answers: NDQ_016400

answers: trans

answers: NDQ_016401

answers: Enoyl-CoA

text: Carbon pentaoxide or carbon pentoxide is an unstable molecular oxide of carbon.  The molecule has been produced and studied at cryogenic temperatures. The molecule is important in atmospheric chemistry and in the study of cold ices in the outer solar system and interstellar space. The substance could form and be present on Ganymede or Triton, moons in the outer solar system. The molecule has a C symmetry.  It consists of a five membered ring with one carbon and four oxygen atoms.  A fifth oxygen atom has a double bond to the carbon. Calculation has resulted in a theoretical structure. The pentagon is not regular, but varies in the length of its sides and angles.  The distance between the oxygen atoms that are not attached to carbon is  1.406 Å, whereas the distance between one of these atoms and an oxygen attached to carbon is 1.457 Å.  The carbon oxygen bond length is 1.376 Å. The double carbon to oxygen bond is the shortest at 1.180 Å. There is no carbon-to-carbon bond as there is only one carbon atom. The OOO bond angle is 100.2° and the OOC angle is 109.1°. The OCO bond angle is 125.4°.

text: Carbon pentaoxide or carbon pentoxide is an unstable molecular

text: oxide of carbon

text: .  The molecule has been produced and studied at cryogenic temperatures. The molecule is important in atmospheric chemistry and in the study of cold ices in the outer solar system and interstellar space. The substance could form and be present on

text: Ganymede

text: or

text: Triton

text: , moons in the outer solar system. The molecule has a C symmetry.  It consists of a five membered ring with one carbon and four oxygen atoms.  A fifth oxygen atom has a double bond to the carbon. Calculation has resulted in a theoretical structure. The pentagon is not regular, but varies in the length of its sides and angles.  The distance between the oxygen atoms that are not attached to carbon is  1.406 Å, whereas the distance between one of these atoms and an oxygen attached to carbon is 1.457 Å.  The carbon oxygen bond length is 1.376 Å. The double carbon to oxygen bond is the shortest at 1.180 Å. There is no carbon-to-carbon bond as there is only one carbon atom. The OOO bond angle is 100.2° and the OOC angle is 109.1°. The OCO bond angle is 125.4°.

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answers: It consists of a five membered ring with one carbon

answers: NDQ_016396

answers: no carbon-to-carbon

answers: NDQ_016398

answers: Carbon pentaoxide

answers: NDQ_016399

answers: no

answers: NDQ_016400

answers: four

answers: NDQ_016401

answers: It consists of a five membered ring

text: Carbon suboxide, or tricarbon dioxide, is an oxide of carbon with chemical formula CO  or O=C=C=C=O.  Its four cumulative double bonds make it a cumulene. It is one of the stable members of the series of linear oxocarbons O=C=O, which also includes carbon dioxide (CO) and pentacarbon dioxide (CO).

text: Carbon suboxide, or tricarbon dioxide, is an

text: oxide

text: of

text: carbon

text: with

text: chemical formula

text: CO  or O=C=C=C=O.  Its four cumulative double bonds make it a

text: cumulene

text: . It is one of the stable members of the series of linear

text: oxocarbon

text: s O=C=O, which also includes

text: carbon dioxide

text: (CO) and

text: pentacarbon dioxide

text: (CO).

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answers: NDQ_016392

answers: Carbon suboxide

answers: NDQ_016396

answers: cumulative double bonds

answers: NDQ_016398

answers: O=C=O

answers: NDQ_016399

answers: cumulene

answers: NDQ_016400

answers: four

answers: NDQ_016401

answers: O=C=O

text: Where double bonds are formed, hydrogen atoms are subtracted from the carbon chain. Thus, a saturated fat has no double bonds, has the maximum number of hydrogens bonded to the carbons, and therefore is "saturated" with hydrogen atoms. In cellular metabolism, unsaturated fat molecules contain somewhat less energy (i.e., fewer calories) than an equivalent amount of saturated fat. The greater the degree of unsaturation in a fatty acid (i.e., the more double bonds in the fatty acid) the more vulnerable it is to lipid peroxidation (rancidity). Antioxidants can protect unsaturated fat from lipid peroxidation.

text: Where double bonds are formed,

text: hydrogen

text: atom

text: s are subtracted from the carbon chain. Thus, a

text: saturated fat

text: has no double bonds, has the maximum number of hydrogens bonded to the carbons, and therefore is "saturated" with hydrogen atoms. In cellular

text: metabolism

text: , unsaturated fat molecules contain somewhat less energy (i.e., fewer

text: calories

text: ) than an equivalent amount of saturated fat. The greater the degree of unsaturation in a fatty acid (i.e., the more double bonds in the fatty acid) the more vulnerable it is to

text: lipid peroxidation

text: rancidity

text: Antioxidant

text: s can protect unsaturated fat from lipid peroxidation.

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answers: carbon

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answers: maximum number of hydrogens

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answers: Hydrocarbon

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answers: unsaturated fat

answers: NDQ_016400

answers: double bonds

answers: NDQ_016401

answers: double bonds

text: The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vinyl halide.

text: The Sonogashira reaction is a

text: cross-coupling reaction

text: used in

text: organic synthesis

text: to form

text: carbon–carbon bond

text: s. It employs a

text: palladium

text: catalyst

text: to form a carbon–carbon bond between a terminal

text: alkyne

text: and an

text: aryl

text: or

text: vinyl halide

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answers: carbon

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answers: carbon–carbon

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answers: carbon–carbon bond

answers: NDQ_016399

answers: Sonogashira

answers: NDQ_016400

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answers: NDQ_016401

answers: carbon

text: It is known that the amine groups (nitrogen atom bonded to carbon and or hydrogen exhibiting a valence pair of electrons) are responsible for the sensitization of nitromethane, chemical formula CHNO. It is thought that the amine weakens the C-N bond in the nitromethane, resulting in less energy being needed to break the bond, thus detonation.

text: It is known that the

text: amine

text: groups (nitrogen atom bonded to carbon and or hydrogen exhibiting a valence pair of electrons) are responsible for the sensitization of nitromethane, chemical formula CHNO. It is thought that the amine weakens the C-N

text: bond

text: in the nitromethane, resulting in less energy being needed to break the bond, thus detonation.

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answers: C-N bond

answers: NDQ_016396

answers: C-N bond

answers: NDQ_016398

answers: nitromethane

answers: NDQ_016399

answers: C-N bond

answers: NDQ_016400

answers: valence pair

answers: NDQ_016401

answers: C-N bond

text: The organic compound -isoleucine molecule presents some features typical of organic compounds:  carbon–carbon bonds, carbon–hydrogen bonds, as well as covalent bonds between carbon to oxygen and to nitrogen.

text: The organic compound

text: -isoleucine

text: molecule presents some features typical of organic compounds:

text: carbon–carbon bond

text: s,

text: carbon–hydrogen bond

text: s, as well as covalent bonds between carbon to oxygen and to nitrogen.

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text: Similarly for all practical purposes, C signal splitting due to coupling with nearby natural isotopic abundance carbons is negligible in C NMR spectra.  However, practically all hydrogen bonded to carbon atoms is H in natural isotopic abundance samples, including any C nuclei bonded to H atoms.  In a C spectrum with no decoupling at all, each of the C signals is split according to how many H atoms that C atom is next to.  In order to simplify the spectrum, C NMR spectroscopy is most often run fully proton decoupled, meaning H nuclei in the sample are broadly irradiated to fully decouple them from the C nuclei being analyzed.  This full proton decoupling eliminates all coupling with H atoms and thus splitting due to H atoms in natural isotopic abundance compounds.  Since coupling between other carbons in natural isotopic abundance samples is negligible, signals in fully proton decoupled C spectra in hydrocarbons and most signals from other organic compounds are single peaks.  This way, the number of equivalent sets of carbon atoms in a chemical structure can be counted by counting singlet peaks, which in C spectra tend to be very narrow (thin).  Other information about the carbon atoms can usually be determined from the chemical shift, such as whether the atom is part of a carbonyl group or an aromatic ring, etc.  Such full proton decoupling can also help increase the intensity of C signals.

text: Similarly for all practical purposes, C signal splitting due to coupling with nearby natural isotopic abundance carbons is negligible in C NMR spectra.  However, practically all hydrogen bonded to carbon atoms is H in natural isotopic abundance samples, including any C nuclei bonded to H atoms.  In a C spectrum with no decoupling at all, each of the C signals is split according to how many H atoms that C atom is next to.  In order to simplify the spectrum, C NMR spectroscopy is most often run fully proton decoupled, meaning H nuclei in the sample are broadly irradiated to fully decouple them from the C nuclei being analyzed.  This full proton decoupling eliminates all coupling with H atoms and thus splitting due to H atoms in natural isotopic abundance compounds.  Since coupling between other carbons in natural isotopic abundance samples is negligible, signals in fully proton decoupled C spectra in

text: hydrocarbon

text: s and most signals from other organic compounds are single peaks.  This way, the number of equivalent sets of carbon atoms in a

text: chemical structure

text: can be counted by counting singlet peaks, which in C spectra tend to be very narrow (thin).  Other information about the carbon atoms can usually be determined from the

text: chemical shift

text: , such as whether the atom is part of a

text: carbonyl group

text: or an

text: aromatic

text: ring, etc.  Such full proton decoupling can also help increase the intensity of C signals.

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answers: hydrocarbons and most signals from other organic compounds

text: Atoms of chemically pure elements may bond to each other chemically in more than one way, allowing the pure element to exist in multiple chemical structures (spatial arrangements of atoms), known as allotropes, which differ in their properties. For example, carbon can be found as diamond, which has a tetrahedral structure around each carbon atom; graphite, which has layers of carbon atoms with a hexagonal structure stacked on top of each other; graphene, which is a single layer of graphite that is very strong; fullerenes, which have nearly spherical shapes; and carbon nanotubes, which are tubes with a hexagonal structure (even these may differ from each other in electrical properties). The ability of an element to exist in one of many structural forms is known as 'allotropy'.

text: Atoms of chemically pure elements may bond to each other chemically in more than one way, allowing the pure element to exist in multiple

text: chemical structure

text: s (

text: spatial arrangements of atoms

text: ), known as

text: allotropes

text: , which differ in their properties. For example, carbon can be found as

text: diamond

text: , which has a tetrahedral structure around each carbon atom;

text: graphite

text: , which has layers of carbon atoms with a hexagonal structure stacked on top of each other;

text: graphene

text: , which is a single layer of graphite that is very strong;

text: fullerene

text: s, which have nearly spherical shapes; and

text: carbon nanotube

text: s, which are tubes with a hexagonal structure (even these may differ from each other in electrical properties). The ability of an element to exist in one of many structural forms is known as 'allotropy'.

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answers: more than one way

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answers: Tetrahedral structure

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answers: carbon can be found as diamond

text: Phosphatidic acid consists of a glycerol backbone, with, in general, a saturated fatty acid bonded to carbon-1, an unsaturated fatty acid bonded to carbon-2, and a phosphate group bonded to carbon-3.

text: Phosphatidic acid consists of a

text: glycerol

text: backbone, with, in general, a saturated

text: fatty acid

text: bonded to

text: carbon

text: -1, an unsaturated

text: fatty acid

text: bonded to

text: carbon

text: -2, and a

text: phosphate

text: group bonded to

text: carbon

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text: As it functions in the step immediately preceding the actual beta-oxidation and forms a double bond extending from the beta-carbon (position 2), enoyl-CoA isomerase is involved in both the NADPH-dependent and NADPH-independent pathways of beta-oxidation. The double bond serves as the target of oxidation and carbon-to-carbon bond cleavage, thereby shortening the fatty acid chain.

text: As it functions in the step immediately preceding the actual

text: beta-oxidation

text: and forms a

text: double bond

text: extending from the beta-

text: carbon

text: (position 2), enoyl-CoA

text: isomerase

text: is involved in both the

entity_name: Nicotinamide adenine dinucleotide phosphate

text: NADPH

text: -dependent and

text: NADPH

text: -independent pathways of

text: beta-oxidation

text: . The

text: double bond

text: serves as the target of

text: oxidation

text: and

text: carbon

text: -to-

text: carbon

text: bond cleavage

text: , thereby shortening the

text: fatty acid

text: chain.

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text: The triangular structure of cyclopropane requires the bond angles  between carbon-carbon bonds to be 60°. This is far less than the thermodynamically most stable angle of 109.5° (for bonds between atoms with sp hybridised orbitals) and leads to significant ring strain. The molecule also has torsional strain due to the eclipsed conformation of its hydrogen atoms. As such, the bonds between the carbon atoms are considerably weaker than in a typical alkane, resulting in much higher reactivity.

text: The triangular structure of cyclopropane requires the

text: bond angle

text: s  between carbon-carbon bonds to be 60°. This is far less than the thermodynamically most stable angle of 109.5° (for bonds between atoms with sp

text: hybridised orbitals

text: ) and leads to significant

text: ring strain

text: . The molecule also has torsional strain due to the

text: eclipsed conformation

text: of its hydrogen atoms. As such, the bonds between the carbon atoms are considerably weaker than in a typical

text: alkane

text: , resulting in much higher reactivity.

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text: The sodium carbonate test (not to be confused with sodium carbonate extract test) is used to distinguish between some common metal ions, which are precipitated as their respective carbonates. The test can distinguish between copper (Cu), iron (Fe), and calcium (Ca), zinc (Zn) or lead (Pb). Sodium carbonate solution is added to the salt of the metal. A blue precipitate indicates Cu ion. A dirty green precipitate indicates Fe ion. A yellow-brown precipitate indicates Fe ion. A white precipitate indicates Ca, Zn, or Pb ion.  The compounds formed are, respectively, copper(II) carbonate, iron(II) carbonate, iron(III) oxide, calcium carbonate, zinc carbonate, and lead(II) carbonate. This test is used to precipitate the ion present as almost all carbonates are insoluble. While this test is useful for telling these cations apart, it fails if other ions are present, because most metal carbonates are insoluble and will precipitate. In addition, calcium, zinc, and lead ions all produce white precipitates with carbonate, making it difficult to distinguish between them. Instead of sodium carbonate, sodium hydroxide may be added, this gives nearly the same colours, except that lead and zinc hydroxides are soluble in excess alkali, and can hence be distinguished from calcium. For the complete sequence of tests used for qualitative cation analysis, see qualitative inorganic analysis.

text: The sodium carbonate test (not to be confused with sodium carbonate extract test) is used to distinguish between some common metal ions, which are precipitated as their respective carbonates. The test can distinguish between copper (Cu), iron (Fe), and calcium (Ca), zinc (Zn) or lead (Pb). Sodium carbonate solution is added to the salt of the metal. A blue precipitate indicates Cu ion. A dirty green precipitate indicates Fe ion. A yellow-brown precipitate indicates Fe ion. A white precipitate indicates Ca, Zn, or Pb ion.  The compounds formed are, respectively,

text: copper(II) carbonate

text: iron(II) carbonate

text: iron(III) oxide

text: calcium carbonate

text: zinc carbonate

text: , and

text: lead(II) carbonate

text: . This test is used to precipitate the ion present as almost all carbonates are insoluble. While this test is useful for telling these cations apart, it fails if other ions are present, because most metal carbonates are insoluble and will precipitate. In addition, calcium, zinc, and lead ions all produce white precipitates with carbonate, making it difficult to distinguish between them. Instead of sodium carbonate,

text: sodium hydroxide

text: may be added, this gives nearly the same colours, except that lead and zinc hydroxides are soluble in excess alkali, and can hence be distinguished from calcium. For the complete sequence of tests used for qualitative cation analysis, see

text: qualitative inorganic analysis

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answers: almost all carbonates are insoluble

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answers: calcium carbonate

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answers: Calcium carbonate

text: Even though QM/MM methods are often very efficient, they are still rather tricky to handle. A researcher has to limit the regions (atomic sites) which are simulated by QM. Moving the limitation borders can both effect the results and the time computing the results. The way the QM and MM systems are coupled can differ substantially depending on the arrangement of particles in the system and their deviations from equilibrium positions in time. Usually limits are set at carbon-carbon bonds and avoided in regions that are associated with charged groups, since such an electronically variant limit can influence the quality of the model.

text: Even though QM/MM methods are often very efficient, they are still rather tricky to handle. A researcher has to limit the regions (atomic sites) which are simulated by QM. Moving the limitation borders can both effect the results and the time computing the results. The way the QM and MM systems are coupled can differ substantially depending on the arrangement of particles in the system and their deviations from equilibrium positions in time. Usually limits are set at carbon-carbon bonds and avoided in regions that are associated with charged groups, since such an electronically variant limit can influence the quality of the model.

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text: Boranes react rapidly to alkenes in a process called hydroboration. This concept was discovered by Dr. Herbert Charles Brown, work for which he eventually received the Nobel Prize (jointly with Georg Wittig for his discovery of the Wittig reaction). Although diborane as a pure compound is a dimer, BH forms 1:1 complexes with basic solvents, for instance THF. In an ordinary electrophilic addition reaction of HX (X = Cl, Br, I, etc.), Markovnikov's rule, which states that the less electronegative atom, usually hydrogen, adds to the least substituted carbon of the double bond, this determines regioselectivity. With boranes the mode of action is the same, the hydrogen adds to the most substituted carbon because boron is less electronegative than hydrogen. When a positive charge develops in the alkene on the most substituted carbon atom, that is where the partially negatively charged hydrogen atom adds, leaving the least substituted carbon atom for the boron atom. The so-called anti-Markovnikov addition because when the boron is replaced with a hydroxyl group the overall reaction is addition of water over the double bond in what appears to be an anti-Makovnikov addition.

text: Boranes react rapidly to

text: alkene

text: s in a process called

text: hydroboration

text: . This concept was discovered by Dr.

text: Herbert Charles Brown

text: , work for which he eventually received the

text: Nobel Prize

text: (jointly with

text: Georg Wittig

text: for his discovery of the

text: Wittig reaction

text: ). Although diborane as a pure compound is a dimer, BH forms 1:1 complexes with basic solvents, for instance

text: THF

text: . In an ordinary

text: electrophilic addition

text: reaction of HX (X = Cl, Br, I, etc.),

text: Markovnikov's rule

text: , which states that the less electronegative atom, usually hydrogen, adds to the least substituted carbon of the double bond, this determines

text: regioselectivity

text: . With boranes the mode of action is the same, the hydrogen adds to the most substituted carbon because boron is less

text: electronegative

text: than hydrogen. When a positive charge develops in the alkene on the most substituted carbon atom, that is where the partially negatively charged hydrogen atom adds, leaving the least substituted carbon atom for the boron atom. The so-called anti-Markovnikov addition because when the boron is replaced with a hydroxyl group the overall reaction is addition of water over the double bond in what appears to be an anti-Makovnikov addition.

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answers: Alkenes

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text: The ability of an element to catenate is primarily based on the bond energy of the element to itself, which decreases with more diffuse orbitals (those with higher azimuthal quantum number) overlapping to form the bond.  Hence, carbon, with the least diffuse valence shell p orbital is capable of forming longer p-p sigma bonded chains of atoms than heavier elements which bond via higher valence shell orbitals.  Catenation ability is also influenced by a range of steric and electronic factors, including the electronegativity of the element in question, the molecular orbital hybridization and the ability to form different kinds of covalent bonds. For carbon, the sigma overlap between adjacent atoms is sufficiently strong that perfectly stable chains can be formed. With other elements this was once thought to be extremely difficult in spite of plenty of evidence to the contrary.

text: The ability of an element to catenate is primarily based on the

text: bond energy

text: of the element to itself, which decreases with more diffuse orbitals (those with higher

text: azimuthal quantum number

text: ) overlapping to form the bond.  Hence, carbon, with the least diffuse valence shell p orbital is capable of forming longer p-p sigma bonded chains of atoms than heavier elements which bond via higher valence shell orbitals.  Catenation ability is also influenced by a range of

text: steric

text: and electronic factors, including the

text: electronegativity

text: of the element in question, the

text: molecular orbital

text: hybridization and the ability to form different kinds of covalent bonds. For carbon, the sigma overlap between adjacent atoms is sufficiently strong that perfectly stable chains can be formed. With other elements this was once thought to be extremely difficult in spite of plenty of evidence to the contrary.

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answers: The ability of an element to catenate

text: The concept of the chemical bond as a direct link between atoms can be modelled by linking balls (atoms) with sticks/rods (bonds). This has been extremely popular and is still widely used today. Initially atoms were made of spherical wooden balls with specially drilled holes for rods. Thus carbon can be represented as a sphere with four holes at the tetrahedral angles cos(-1/3) ≈ 109.47° .

text: The concept of the chemical bond as a direct link between atoms can be modelled by linking balls (atoms) with sticks/rods (bonds). This has been extremely popular and is still widely used today. Initially atoms were made of spherical wooden balls with specially drilled holes for rods. Thus

text: carbon

text: can be represented as a sphere with four holes at the

text: tetrahedral

text: angles cos(-1/3) ≈ 109.47° .

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answers: tetrahedral angles

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answers: It has been extremely popular

text: Increasing concentrations of carbon in the alloy widen the electronic gap between conduction and valence bands (also called "optical gap" and bandgap).  This can potentially increase the light efficiency of solar cells made with amorphous silicon carbide layers. On the other hand, the electronic properties as a semiconductor (mainly electron mobility), are adversely affected by the increasing content of carbon in the alloy, due to the increased disorder in the atomic network.

text: Increasing concentrations of carbon in the alloy widen the electronic gap between conduction and valence bands (also called "optical gap" and

text: bandgap

text: ).  This can potentially increase the light efficiency of solar cells made with amorphous silicon carbide layers. On the other hand, the electronic properties as a

text: semiconductor

text: (mainly

text: electron mobility

text: ), are adversely affected by the increasing content of carbon in the alloy, due to the increased disorder in the atomic network.

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answers: The electronic properties as a semiconductor

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answers: The electronic properties as a semiconductor

text: In chemistry, coordination number (c.n.), defined originally in 1893 by Alfred Werner, is the total number of neighbors of a central atom in a molecule or ion. Although a carbon atom has four chemical bonds in most stable molecules, the coordination number of each carbon is four in methane (CH), three in ethylene (HC=CH, each C is bonded to 2H + 1C = 3 atoms), and two in acetylene (HC≡CH). In effect we count the first bond (or sigma bond) to each neighboring atom, but not the other bonds (pi bonds).

text: In chemistry, coordination number (c.n.), defined originally in 1893 by

text: Alfred Werner

text: , is the total number of neighbors of a central atom in a molecule or ion. Although a carbon atom has four

text: chemical bonds

text: in most stable molecules, the coordination number of each

text: carbon

text: is four in

text: methane

text: (CH), three in

text: ethylene

text: (HC=CH, each C is bonded to 2H + 1C = 3 atoms), and two in

text: acetylene

text: (HC≡CH). In effect we count the first bond (or

text: sigma bond

text: ) to each neighboring atom, but not the other bonds (

text: pi bond

text: s).

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answers: Most stable molecules

answers: NDQ_016396

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answers: NDQ_016399

answers: ethylene

answers: NDQ_016400

answers: 3 atoms

answers: NDQ_016401

answers: Carbon can form more compounds than any other element.

text: In molecules that have resonance or nonclassical bonding, bond order does not need to be an integer. In benzene, where the delocalized molecular orbitals contain 6 pi electrons over six carbons essentially yielding half a pi bond together with the sigma bond for each pair of carbon atoms, giving a calculated bond order of 1.5. Furthermore, bond orders of 1.1, for example, can arise under complex scenarios and essentially refer to bond strength relative to bonds with order 1.

text: In molecules that have

text: resonance

text: or nonclassical bonding, bond order does not need to be an integer. In

text: benzene

text: , where the delocalized

text: molecular orbital

text: s contain 6

text: pi electron

text: s over six carbons essentially yielding half a

text: pi bond

text: together with the

text: sigma bond

text: for each pair of carbon atoms, giving a calculated bond order of 1.5. Furthermore, bond orders of 1.1, for example, can arise under complex scenarios and essentially refer to bond strength relative to bonds with order 1.

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answers: Benzene

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answers: Benzene

text: In an extreme case the central carbon atom ordinarily with a tetrahedral molecular geometry gets completely flattened. In the molecular orbital picture for square planar methane two of a total of three sp-hybridized carbon atomic orbitals form regular bonds with two of the hydrogen atoms as in a planar alkene. The third sp-orbital interacts in a three-center two-electron bond with the two remaining hydrogen atoms utilizing  only the hydrogen electrons. Two additional carbon valence electrons are situated in a p-orbital perpendicular to the plane of the molecule. The four C–H bonds are equal because they resonate. In silico calculations show that it takes 95 to 250 kcal/mol (400 to 1,050 kJ/mol) for this process.

text: In an extreme case the central carbon atom ordinarily with a

text: tetrahedral molecular geometry

text: gets completely flattened. In the

text: molecular orbital

text: picture for

text: square planar

text: methane

text: two of a total of three

text: sp-hybridized

text: carbon atomic orbitals form regular bonds with two of the hydrogen atoms as in a planar

text: alkene

text: . The third sp-orbital interacts in a

text: three-center two-electron bond

text: with the two remaining hydrogen atoms utilizing  only the hydrogen electrons. Two additional carbon

text: valence electron

text: s are situated in a p-orbital perpendicular to the plane of the molecule. The four C–H bonds are equal because they

text: resonate

text: In silico

text: calculations show that it takes 95 to 250 kcal/mol (400 to 1,050 kJ/mol) for this process.

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answers: Carbon can form more compounds than any other element

text: A condensed chemical formula may represent the types and spatial arrangement of bonds in a simple chemical substance, though it does not necessarily specify isomers or complex structures. For example, ethane consists of two carbon atoms single-bonded to each other, with each carbon atom having three hydrogen atoms bonded to it. Its chemical formula can be rendered as CHCH. In ethylene there is a double bond between the carbon atoms (and thus each carbon only has two hydrogens), therefore the chemical formula may be written: CHCH, and the fact that there is a double bond between the carbons is implicit because carbon has a valence of four. However, a more explicit method is to write HC=CH or less commonly HC::CH. The two lines (or two pairs of dots) indicate that a double bond connects the atoms on either side of them.

text: A condensed chemical formula may represent the types and spatial arrangement of

text: bonds

text: in a simple chemical substance, though it does not necessarily specify

text: isomer

text: s or complex structures. For example,

text: ethane

text: consists of two carbon atoms single-bonded to each other, with each carbon atom having three hydrogen atoms bonded to it. Its chemical formula can be rendered as CHCH. In

text: ethylene

text: there is a double bond between the carbon atoms (and thus each carbon only has two hydrogens), therefore the chemical formula may be written: CHCH, and the fact that there is a double bond between the carbons is implicit because carbon has a valence of four. However, a more explicit method is to write HC=CH or less commonly HC::CH. The two lines (or two pairs of dots) indicate that a

text: double bond

text: connects the atoms on either side of them.

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answers: valence of four

text: In organic chemistry, an alkene is an unsaturated hydrocarbon that contains at least one carbon–carbon double bond. The words alkene, olefin, and olefine are used often interchangeably (see nomenclature section below).  Acyclic alkenes, with only one double bond and no other functional groups, known as mono-enes, form a homologous series of hydrocarbons with the general formula . Alkenes have two hydrogen atoms less than the corresponding alkane (with the same number of carbon atoms). The simplest alkene, ethylene (CH), with the International Union of Pure and Applied Chemistry (IUPAC) name ethene, is the organic compound produced on the largest scale industrially. Aromatic compounds are often drawn as cyclic alkenes, but their structure and properties are different and they are not considered to be alkenes.

text: In

text: organic chemistry

text: , an alkene is an

text: unsaturated hydrocarbon

text: that contains at least one

text: carbon

text: –carbon

text: double bond

text: . The words alkene, olefin, and olefine are used often interchangeably (see

text: nomenclature

text: section below).  Acyclic alkenes, with only one double bond and no other

text: functional group

text: s, known as mono-enes, form a

text: homologous series

text: of

text: hydrocarbon

text: s with the general formula . Alkenes have two

text: hydrogen

text: atoms

text: less than the corresponding

text: alkane

text: (with the same number of carbon atoms). The simplest alkene,

text: ethylene

text: (CH), with the

entity_name: International Union of Pure and Applied Chemistry

text: International Union of Pure and Applied Chemistry

text: (IUPAC) name ethene, is the

text: organic compound

text: produced on the largest scale industrially.

text: Aromatic

text: compounds are often drawn as cyclic alkenes, but their structure and properties are different and they are not considered to be alkenes.

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text: Since they are out of the plane of the atoms, these orbitals can interact with each other freely, and become delocalized. This means that, instead of being tied to one atom of carbon, each electron is shared by all six in the ring. Thus, there are not enough electrons to form double bonds on all the carbon atoms, but the "extra" electrons strengthen all of the bonds on the ring equally. The resulting molecular orbital is considered to have π symmetry.

text: Since they are out of the plane of the atoms, these orbitals can interact with each other freely, and become delocalized. This means that, instead of being tied to one atom of carbon, each electron is shared by all six in the ring. Thus, there are not enough electrons to form double bonds on all the carbon atoms, but the "extra" electrons strengthen all of the bonds on the ring equally. The resulting

text: molecular orbital

text: is considered to have π symmetry.

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answers: It can form more compounds than any other element.

text: For example, butadiene has pi orbitals which are delocalized over all four carbon atoms. There are two bonding pi orbitals which are occupied in the ground state: π is bonding between all carbons, while π is bonding between C and C and between C and C, and antibonding between C and C. There are also antibonding pi orbitals with two and three antibonding interactions as shown in the diagram; these are vacant in the ground state, but may be occupied in excited states.

text: For example,

text: butadiene

text: has

text: pi orbital

text: s which are delocalized over all four carbon atoms. There are two bonding pi orbitals which are occupied in the

text: ground state

text: : π is bonding between all carbons, while π is bonding between C and C and between C and C, and antibonding between C and C. There are also antibonding pi orbitals with two and three antibonding interactions as shown in the diagram; these are vacant in the

text: ground state

text: , but may be occupied in

text: excited state

text: s.

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text: The basic method of making margarine today consists of emulsifying a blend of vegetable oils and fats, which can be modified using fractionation, interesterification, and/or hydrogenation, with skimmed milk, chilling the mixture to solidify it and working it to improve the texture. Vegetable and animal fats are similar compounds with different melting points. Those fats that are liquid at room temperature are generally known as oils. The melting points are related to the presence of carbon-carbon double bonds in the fatty acids components. A higher number of double bonds gives a lower melting point.

text: The basic method of making margarine today consists of emulsifying a blend of vegetable oils and fats, which can be modified using fractionation, interesterification, and/or hydrogenation, with skimmed milk, chilling the mixture to solidify it and working it to improve the texture. Vegetable and animal fats are similar compounds with different

text: melting point

text: s. Those fats that are liquid at room temperature are generally known as

text: oil

text: s. The melting points are related to the presence of carbon-carbon double bonds in the fatty acids components. A higher number of double bonds gives a lower melting point.

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text: Conducting polymers have backbones of contiguous sp hybridized carbon centers. One valence electron on each center resides in a p orbital, which is orthogonal to the other three sigma-bonds. The electrons in these delocalized orbitals have high mobility when the material is doped by oxidation, which removes some of these delocalized electrons. Thus the conjugated p-orbitals form a one-dimensional electronic band, and the electrons within this band become mobile when it is emptied partly.  Despite intensive research, the relationship between morphology, chain structure, and conductivity is poorly understood yet.

text: Conducting polymers have backbones of contiguous sp hybridized carbon centers. One valence electron on each center resides in a p orbital, which is orthogonal to the other three sigma-bonds. The electrons in these delocalized orbitals have high mobility when the material is doped by oxidation, which removes some of these delocalized electrons. Thus the

text: conjugated

text: p-orbitals form a one-dimensional

text: electronic band

text: , and the electrons within this band become mobile when it is emptied partly.  Despite intensive research, the relationship between morphology, chain structure, and conductivity is poorly understood yet.

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text: An informal justification of Bent's rule relies on s orbitals being lower in energy than p orbitals. Bonds between elements of different electronegativities will be polar and the electron density in such bonds will be shifted towards the more electronegative element. Applying this to the molecule fluoromethane provides a demonstration of Bent's rule. Because carbon is more electronegative than hydrogen, the electron density in the C-H bonds will be closer to carbon. The energy of those electrons will depend heavily on the hybrid orbitals that carbon contributes to these bonds because of the increased electron density near the carbon. By increasing the amount of s character in those hybrid orbitals, the energy of those electrons can be reduced because s orbitals are lower in energy than p orbitals.

text: An informal justification of Bent's rule relies on s orbitals being lower in energy than p orbitals. Bonds between elements of different

text: electronegativities

text: will be

text: polar

text: and the electron density in such bonds will be shifted towards the more electronegative element. Applying this to the molecule

text: fluoromethane

text: provides a demonstration of Bent's rule. Because carbon is more

text: electronegative

text: than hydrogen, the electron density in the C-H bonds will be closer to carbon. The energy of those electrons will depend heavily on the hybrid orbitals that carbon contributes to these bonds because of the increased electron density near the carbon. By increasing the amount of s character in those hybrid orbitals, the energy of those electrons can be reduced because s orbitals are lower in energy than p orbitals.

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answers: Because carbon is more electronegative than hydrogen

text: The main polymers subjected to vulcanization are polyisoprene (natural rubber) and styrene-butadiene rubber (SBR), which are used for most street-vehicle tires. The "cure package" is adjusted specifically for the substrate and the application. The reactive sites—"cure sites"—are allylic hydrogen atoms. These C-H bonds are adjacent to carbon-carbon double bonds. During vulcanization, some of these C-H bonds are replaced by chains of sulfur atoms that link with a cure site of another polymer chain. These bridges contain between one and eight atoms. The number of sulfur atoms in the crosslink strongly influences the physical properties of the final rubber article. Short crosslinks give the rubber better heat resistance. Crosslinks with higher number of sulfur atoms give the rubber good dynamic properties but less heat resistance. Dynamic properties are important for flexing movements of the rubber article, e.g., the movement of a side-wall of a running tire. Without good flexing properties these movements rapidly form cracks, and ultimately make the rubber article fail.

text: The main polymers subjected to vulcanization are

text: polyisoprene

text: (natural rubber) and

text: styrene-butadiene

text: rubber (SBR), which are used for most street-vehicle tires. The "cure package" is adjusted specifically for the substrate and the application. The reactive sites—"cure sites"—are

text: allyl

text: ic hydrogen atoms. These C-H bonds are adjacent to carbon-carbon double bonds. During vulcanization, some of these C-H bonds are replaced by chains of sulfur atoms that link with a cure site of another polymer chain. These bridges contain between one and eight atoms. The number of sulfur atoms in the crosslink strongly influences the physical properties of the final rubber article. Short crosslinks give the rubber better heat resistance. Crosslinks with higher number of sulfur atoms give the rubber good dynamic properties but less heat resistance. Dynamic properties are important for flexing movements of the rubber article, e.g., the movement of a side-wall of a running tire. Without good flexing properties these movements rapidly form cracks, and ultimately make the rubber article fail.

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text: The oxidation state of carbon in carbon monoxide is +2 in each of these structures. It is calculated by counting all the bonding electrons as belonging to the more electronegative oxygen. Only the two non-bonding electrons on carbon are assigned to carbon. In this count, carbon then has only two valence electrons in the molecule compared to four in the free atom.

text: The

text: oxidation state

text: of carbon in carbon monoxide is +2 in each of these structures. It is calculated by counting all the bonding electrons as belonging to the more electronegative oxygen. Only the two non-bonding electrons on carbon are assigned to carbon. In this count, carbon then has only two valence electrons in the molecule compared to four in the free atom.

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text: In two papers outlining his "theory of atomicity of the elements" (1857–58), Friedrich August Kekulé was the first to offer a theory of how every atom in an organic molecule was bonded to every other atom.  He proposed that carbon atoms were tetravalent, and could bond to themselves to form the carbon skeletons of organic molecules.

text: In two papers outlining his "theory of atomicity of the elements" (1857–58),

text: Friedrich August Kekulé

text: was the first to offer a theory of how every atom in an organic molecule was bonded to every other atom.  He proposed that carbon atoms were tetravalent, and could bond to themselves to form the carbon skeletons of organic molecules.

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answers: Kekulé

text: Because of the diverse range of elements and the correspondingly diverse properties of the resulting derivatives, inorganic chemistry is closely associated with many methods of analysis.  Older methods tended to examine bulk properties such as the electrical conductivity of solutions, melting points, solubility, and acidity.  With the advent of quantum theory and the corresponding expansion of electronic apparatus, new tools have been introduced to probe the electronic properties of inorganic molecules and solids.  Often these measurements provide insights relevant to theoretical models.  For example, measurements on the photoelectron spectrum of methane demonstrated that describing the bonding by the two-center, two-electron bonds predicted  between the carbon and hydrogen using Valence Bond Theory is not appropriate for describing ionisation processes in a simple way. Such insights led to the popularization of molecular orbital theory as fully delocalised orbitals are a more appropriate simple description of electron removal and electron excitation.

text: Because of the diverse range of elements and the correspondingly diverse properties of the resulting derivatives, inorganic chemistry is closely associated with many methods of analysis.  Older methods tended to examine bulk properties such as the electrical conductivity of solutions,

text: melting point

text: s,

text: solubility

text: , and

text: acidity

text: .  With the advent of

text: quantum theory

text: and the corresponding expansion of electronic apparatus, new tools have been introduced to probe the electronic properties of inorganic molecules and solids.  Often these measurements provide insights relevant to theoretical models.  For example, measurements on the

text: photoelectron spectrum

text: of

text: methane

text: demonstrated that describing the bonding by the two-center, two-electron bonds predicted  between the carbon and hydrogen using

text: Valence Bond Theory

text: is not appropriate for describing ionisation processes in a simple way. Such insights led to the popularization of

text: molecular orbital theory

text: as fully delocalised orbitals are a more appropriate simple description of electron removal and electron excitation.

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answers: diverse range of elements and the correspondingly diverse properties

text: Carbon dioxide, , is a linear molecule with a total of sixteen bonding electrons in its valence shell. Carbon is the central atom of the molecule and a principal axis, the z-axis, is visualized as a single axis that goes through the center of carbon and the two oxygens atoms.For convention, blue atomic orbital lobes are positive phases, red atomic orbitals are negative phases, with respect to the wave function from the solution of the Schrödinger equation. In carbon dioxide the carbon 2s (−19.4 eV), carbon 2p (−10.7 eV), and oxygen 2p (−15.9 eV)) energies associated with the atomic orbitals are in proximity whereas the oxygen 2s energy (−32.4 eV) is different.

text: Carbon dioxide

text: , , is a

text: linear molecule

text: with a total of sixteen

text: bonding electrons

text: in its

text: valence shell

text: . Carbon is the central atom of the molecule and a principal axis, the z-axis, is visualized as a single axis that goes through the center of carbon and the two oxygens atoms.For convention, blue atomic orbital lobes are positive phases, red atomic orbitals are negative phases, with respect to the wave function from the solution of the

text: Schrödinger equation

text: . In carbon dioxide the carbon 2s (−19.4 eV), carbon 2p (−10.7 eV), and oxygen 2p (−15.9 eV)) energies associated with the atomic orbitals are in proximity whereas the oxygen 2s energy (−32.4 eV) is different.

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answers: Carbon dioxide

text: At very high pressures, carbon forms the more compact allotrope, diamond, having nearly twice the density of graphite. Here, each atom is bonded tetrahedrally to four others, forming a 3-dimensional network of puckered six-membered rings of atoms. Diamond has the same cubic structure as silicon and germanium, and because of the strength of the carbon-carbon bonds, it is the hardest naturally occurring substance measured by resistance to scratching. Contrary to the popular belief that "diamonds are forever", they are thermodynamically unstable under normal conditions and transform into graphite. Due to a high activation energy barrier, the transition into graphite is so slow at normal temperature that it is unnoticeable. Under some conditions, carbon crystallizes as lonsdaleite, a hexagonal crystal lattice with all atoms covalently bonded and properties similar to those of diamond.

text: At very high pressures, carbon forms the more compact allotrope,

text: diamond

text: , having nearly twice the density of graphite. Here, each atom is bonded

text: tetrahedrally

text: to four others, forming a 3-dimensional network of puckered six-membered rings of atoms. Diamond has the same

text: cubic structure

text: as

text: silicon

text: and

text: germanium

text: , and because of the strength of the carbon-carbon

text: bonds

text: , it is the hardest naturally occurring substance measured by

text: resistance to scratching

text: . Contrary to the popular belief that "

text: diamonds are forever

text: ", they are thermodynamically unstable under normal conditions and transform into

text: graphite

text: . Due to a high activation energy barrier, the transition into graphite is so slow at normal temperature that it is unnoticeable. Under some conditions, carbon crystallizes as

text: lonsdaleite

text: , a

text: hexagonal

text: crystal

text: lattice with all atoms covalently bonded and properties similar to those of diamond.

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answers: It is the hardest naturally occurring substance

text: In 1857, German chemist August Kekulé observed that carbon often has four other atoms bonded to it. Methane, for example, has one carbon atom and four hydrogen atoms. This concept eventually became known as valency; different elements bond with different numbers of atoms.

text: In 1857, German chemist

text: August Kekulé

text: observed that

text: carbon

text: often has four other atoms bonded to it.

text: Methane

text: , for example, has one carbon atom and four hydrogen atoms. This concept eventually became known as

text: valency

text: ; different elements bond with different numbers of atoms.

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text: This bonding pattern is also seen in trimethylaluminium, which forms a dimer Al(CH) with the carbon atoms of two of the methyl groups in bridging positions. This type of bond also occurs in carbon compounds, where it is sometimes referred to as hyperconjugation; another name for asymmetrical three-center two-electron bonds.

text: This bonding pattern is also seen in

text: trimethylaluminium

text: , which forms a dimer Al(CH) with the carbon atoms of two of the

text: methyl group

text: s in bridging positions. This type of bond also occurs in

text: carbon

text: compounds, where it is sometimes referred to as

text: hyperconjugation

text: ; another name for asymmetrical three-center two-electron bonds.

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text: Graphite conducts electricity, due to delocalization of the pi bond electrons above and below the planes of the carbon atoms. These electrons are free to move, so are able to conduct electricity. However, the electricity is only conducted along the plane of the layers. In diamond, all four outer electrons of each carbon atom are 'localised' between the atoms in covalent bonding. The movement of electrons is restricted and diamond does not conduct an electric current. In graphite, each carbon atom uses only 3 of its 4 outer energy level electrons in covalently bonding to three other carbon atoms in a plane. Each carbon atom contributes one electron to a delocalised system of electrons that is also a part of the chemical bonding. The delocalised electrons are free to move throughout the plane. For this reason, graphite conducts electricity along the planes of carbon atoms, but does not conduct in a direction at right angles to the plane.

text: Graphite

text: conducts electricity

text: , due to

text: delocalization

text: of the

text: pi bond

text: electron

text: s above and below the planes of the carbon atoms. These electrons are free to move, so are able to conduct electricity. However, the electricity is only conducted along the plane of the layers. In diamond, all four outer electrons of each carbon atom are 'localised' between the atoms in covalent bonding. The movement of electrons is restricted and diamond does not conduct an electric current. In graphite, each carbon atom uses only 3 of its 4 outer energy level electrons in covalently bonding to three other carbon atoms in a plane. Each carbon atom contributes one electron to a delocalised system of electrons that is also a part of the chemical bonding. The delocalised electrons are free to move throughout the plane. For this reason, graphite conducts electricity along the planes of carbon atoms, but does not conduct in a direction at right angles to the plane.

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text: Another family of carbenes is based on a cyclopropenylidene core, a three-carbon ring with a double bond between the two atoms adjacent to the carbenic one. This family is exemplified by bis(diisopropylamino)cyclopropenylidene.

text: Another family of carbenes is based on a

text: cyclopropenylidene

text: core, a three-carbon ring with a double bond between the two atoms adjacent to the carbenic one. This family is exemplified by

text: bis(diisopropylamino)cyclopropenylidene

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answers: Carbenes

text: Isopentenyl-diphosphate delta isomerase type I (also known as IPP isomerase) is seen in cholesterol synthesis and in particular it catalyzes the conversion of isopentenyl diphosphate (IPP) to dimethylallyl diphosphate (DMAPP). In this isomerization reaction a stable carbon-carbon double bond is rearranged top create a highly electrophilic allylic isomer. IPP isomerase catalyzes this reaction by the stereoselective antarafacial transposition of a single proton. The double bond is protonated at C4 to form a tertiary carbocation intermediate at C3. The adjacent carbon, C2, is deprotonated from the opposite face to yield a double bond.  In effect, the double bond is shifted over.

text: Isopentenyl-diphosphate delta isomerase

text: type I (also known as IPP isomerase) is seen in

text: cholesterol

text: synthesis and in particular it catalyzes the conversion of

text: isopentenyl diphosphate

text: (IPP) to

text: dimethylallyl diphosphate

text: (DMAPP). In this isomerization reaction a stable carbon-carbon double bond is rearranged top create a highly

text: electrophilic

text: allylic isomer

text: . IPP isomerase catalyzes this reaction by the

text: stereoselective

text: antarafacial

text: transposition of a single proton. The

text: double bond

text: is protonated at C4 to form a tertiary

text: carbocation

text: intermediate at C3. The adjacent carbon, C2, is deprotonated from the opposite face to yield a double bond.  In effect, the double bond is shifted over.

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answers: dimethylallyl diphosphate

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answers: IPP isomerase

text: Methane is a tetrahedral molecule with four equivalent C–H bonds. Its electronic structure is described by four bonding molecular orbitals (MOs) resulting from the overlap of the valence orbitals on C and H. The lowest energy MO is the result of the overlap of the 2s orbital on carbon with the in-phase combination of the 1s orbitals on the four hydrogen atoms. Above this energy level is a triply degenerate set of MOs that involve overlap of the 2p orbitals on carbon with various linear combinations of the 1s orbitals on hydrogen. The resulting "three-over-one" bonding scheme is consistent with photoelectron spectroscopic measurements.

text: Methane is a

text: tetrahedral

text: molecule with four equivalent

text: C–H bond

text: s. Its electronic structure is described by four bonding molecular orbitals (MOs) resulting from the overlap of the valence orbitals on

text: C

text: and

text: H

text: . The lowest energy MO is the result of the overlap of the 2s orbital on carbon with the in-phase combination of the 1s orbitals on the four hydrogen atoms. Above this energy level is a triply degenerate set of MOs that involve overlap of the 2p orbitals on carbon with various linear combinations of the 1s orbitals on hydrogen. The resulting "three-over-one" bonding scheme is consistent with photoelectron spectroscopic measurements.

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answers: carbon

text: It is a small carbon cluster first spectroscopically observed in the beginning 20th century in the tail of a comet by William Huggins and subsequently identified in stellar atmospheres. Tricarbon can be found in interstellar space and can be produced in the laboratory by a process called laser ablation. Small carbon clusters like tricarbon and dicarbon are regarded as soot precursors and are implicated in the formation of certain industrial diamonds and in the formation of fullerenes. The ground state molecular geometry of tricarbon has been identified as linear via its characteristic symmetric and antisymmetric stretching and bending vibrational modes and bears bond lengths of 129 to 130 picometer corresponding to those of alkenes. The ionization potential is determined experimentally at 11 to 13.5 electron-volts. In contrast to the linear tricarbon molecule the C cation is bent.

text: It is a small

text: carbon

text: cluster first

text: spectroscopically

text: observed in the beginning 20th century in the tail of a comet by

text: William Huggins

text: and subsequently identified in

text: stellar atmosphere

text: s. Tricarbon can be found in interstellar space and can be produced in the laboratory by a process called

text: laser ablation

text: . Small carbon clusters like tricarbon and

text: dicarbon

text: are regarded as soot precursors and are implicated in the formation of certain industrial

text: diamond

text: s and in the formation of

text: fullerene

text: s. The ground state

text: molecular geometry

text: of tricarbon has been identified as linear via its characteristic symmetric and antisymmetric stretching and bending vibrational modes and bears

text: bond length

text: s of 129 to 130

text: picometer

text: corresponding to those of

text: alkene

text: s. The

text: ionization potential

text: is determined experimentally at 11 to 13.5

text: electron-volt

text: s. In contrast to the linear tricarbon molecule the C

text: cation

text: is bent.

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answers: alkenes

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answers: 129 to 130 picometer

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answers: 11 to 13.5

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answers: Fullerenes

text: A carbon–carbon bond is a covalent bond between two carbon atoms.  The most common form is the single bond: a bond composed of two electrons, one from each of the two atoms. The carbon–carbon single bond is a sigma bond and is formed between one hybridized orbital from each of the carbon atoms. In ethane, the orbitals are sp-hybridized orbitals, but single bonds formed between carbon atoms with other hybridisations do occur (e.g. sp to sp). In fact, the carbon atoms in the single bond need not be of the same hybridisation. Carbon atoms can also form double bonds in compounds called alkenes or triple bonds in compounds called alkynes. A double bond is formed with an sp-hybridized orbital and a p-orbital that isn't involved in the hybridization. A triple bond is formed with an sp-hybridized orbital and two p-orbitals from each atom. The use of the p-orbitals forms a pi bond.

text: A carbon–carbon bond is a

text: covalent bond

text: between two

text: carbon

text: atom

text: s.  The most common form is the

text: single bond

text: : a bond composed of two

text: electron

text: s, one from each of the two atoms. The carbon–carbon single bond is a

text: sigma bond

text: and is formed between one

text: hybridized

text: orbital from each of the carbon atoms. In

text: ethane

text: , the orbitals are sp-

text: hybridized

text: orbitals, but single bonds formed between carbon atoms with other hybridisations do occur (e.g. sp to sp). In fact, the carbon atoms in the single bond need not be of the same hybridisation. Carbon atoms can also form

text: double bond

text: s in compounds called

text: alkene

text: s or

text: triple bond

text: s in compounds called

text: alkyne

text: s. A double bond is formed with an sp-hybridized orbital and a p-orbital that isn't involved in the hybridization. A triple bond is formed with an sp-hybridized orbital and two p-orbitals from each atom. The use of the p-orbitals forms a

text: pi bond

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answers: It can form more compounds than any other element.

text: Kroto was educated at Bolton School alongside Robert Walker Hay and went to the University of Sheffield in 1958, where he obtained a first-class honours BSc degree in Chemistry (1961) and a PhD in Molecular Spectroscopy (1964).  During his time at Sheffield he also was the art editor of "Arrows" – the University student magazine, played tennis for the University team (reaching the UAU finals twice) and was President of the Student Athletics Council (1963–64). Among other things such as making the first phosphaalkenes (compounds with carbon phosphorus double bonds), his doctoral studies included unpublished research on carbon suboxide, O=C=C=C=O, and this led to a general interest in molecules containing chains of carbon atoms with numerous multiple bonds. He started his work with an interest in organic chemistry, but when he learned about spectroscopy it inclined him towards quantum chemistry; he later developed an interest in astrochemistry.

text: Kroto was educated at Bolton School alongside

text: Robert Walker Hay

text: and went to the University of Sheffield in 1958, where he obtained a first-class honours BSc degree in Chemistry (1961) and a PhD in Molecular Spectroscopy (1964).  During his time at Sheffield he also was the art editor of "Arrows" – the University student magazine, played tennis for the University team (reaching the UAU finals twice) and was President of the Student Athletics Council (1963–64). Among other things such as making the first

text: phosphaalkenes

text: (compounds with carbon phosphorus double bonds), his doctoral studies included unpublished research on

text: carbon suboxide

text: , O=C=C=C=O, and this led to a general interest in

text: molecule

text: s containing chains of carbon atoms with numerous multiple bonds. He started his work with an interest in

text: organic chemistry

text: , but when he learned about

text: spectroscopy

text: it inclined him towards

text: quantum chemistry

text: ; he later developed an interest in

text: astrochemistry

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text: Lewis proposed that an atom forms enough covalent bonds to form a full (or closed) outer electron shell. In the methane diagram shown here, the carbon atom has a valence of four and is, therefore, surrounded by eight electrons (the octet rule), four from the carbon itself and four from the hydrogens bonded to it. Each hydrogen has a valence of one and is surrounded by two electrons (a duet rule) – its own one electron plus one from the carbon. The numbers of electrons correspond to full shells in the quantum theory of the atom; the outer shell of a carbon atom is the n = 2 shell, which can hold eight electrons, whereas the outer (and only) shell of a hydrogen atom is the n = 1 shell, which can hold only two.

text: Lewis proposed that an atom forms enough covalent bonds to form a full (or closed) outer electron shell. In the methane diagram shown here, the carbon atom has a valence of four and is, therefore, surrounded by eight electrons (the

text: octet rule

text: ), four from the carbon itself and four from the hydrogens bonded to it. Each hydrogen has a valence of one and is surrounded by two electrons (a duet rule) – its own one electron plus one from the carbon. The numbers of electrons correspond to full shells in the quantum theory of the atom; the outer shell of a carbon atom is the n = 2 shell, which can hold eight electrons, whereas the outer (and only) shell of a hydrogen atom is the n = 1 shell, which can hold only two.

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text: Chemical structures may be written in more compact forms, particularly when showing organic molecules. In condensed structural formulas, many or even all of the covalent bonds may be left out, with subscripts indicating the number of identical groups attached to a particular atom.Another shorthand structural diagram is the skeletal formula (also known as a bond-line formula or carbon skeleton diagram). In a skeletal formula, carbon atoms are not signified by the symbol C but by the vertices of the lines. Hydrogen atoms bonded to carbon are not shown—they can be inferred by counting the number of bonds to a particular carbon atom—each carbon is assumed to have four bonds in total, so any bonds not shown are, by implication, to hydrogen atoms.

text: Chemical structures may be written in more compact forms, particularly when showing

text: organic molecules

text: . In condensed structural formulas, many or even all of the covalent bonds may be left out, with subscripts indicating the number of identical groups attached to a particular atom.Another shorthand structural diagram is the

text: skeletal formula

text: (also known as a bond-line formula or carbon skeleton diagram). In a skeletal formula, carbon atoms are not signified by the symbol C but by the

text: vertices

text: of the lines. Hydrogen atoms bonded to carbon are not shown—they can be inferred by counting the number of bonds to a particular carbon atom—each carbon is assumed to have four bonds in total, so any bonds not shown are, by implication, to hydrogen atoms.

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answers: each carbon is assumed to have four bonds in total

text: Boron is adjacent to carbon in the periodic table and has similar valence orbitals. Unlike carbon, boron cannot form a honeycomb hexagonal framework (like graphene) because of its electron deficiency.

text: Boron is adjacent to

text: carbon

text: in the

text: periodic table

text: and has similar

text: valence orbital

text: s. Unlike carbon, boron cannot form a

text: honeycomb

text: hexagonal framework (like graphene) because of its electron deficiency.

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text: Nylon 66 can have multiple parallel strands aligned with their neighboring peptide bonds at coordinated separations of exactly 6 and 4 carbons for considerable lengths, so the carbonyl oxygens and amide hydrogens can line up to form interchain hydrogen bonds repeatedly, without interruption (see the figure opposite). Nylon 510 can have coordinated runs of 5 and 8 carbons. Thus parallel (but not antiparallel) strands can participate in extended, unbroken, multi-chain β-pleated sheets, a strong and tough supermolecular structure similar to that found in natural silk fibroin and the β-keratins in feathers. (Proteins have only an amino acid α-carbon separating sequential -CO-NH- groups.) Nylon 6 will form uninterrupted H-bonded sheets with mixed directionalities, but the β-sheet wrinkling is somewhat different. The three-dimensional disposition of each alkane hydrocarbon chain depends on rotations about the 109.47° tetrahedral bonds of singly bonded carbon atoms.

text: Nylon 66 can have multiple parallel strands aligned with their neighboring peptide bonds at coordinated separations of exactly 6 and 4 carbons for considerable lengths, so the

text: carbonyl

text: oxygen

text: s and amide

text: hydrogen

text: s can line up to form interchain

text: hydrogen bond

text: s repeatedly, without interruption (see the figure opposite). Nylon 510 can have coordinated runs of 5 and 8 carbons. Thus parallel (but not antiparallel) strands can participate in extended, unbroken, multi-chain

text: β-pleated sheets

text: , a strong and tough supermolecular structure similar to that found in natural

text: silk fibroin

text: and the

text: β-keratins

text: in

text: feather

text: s. (Proteins have only an amino acid α-carbon separating sequential -CO-NH- groups.) Nylon 6 will form uninterrupted

text: H-bonded

text: sheets with mixed directionalities, but the β-sheet wrinkling is somewhat different. The three-dimensional disposition of each

text: alkane

text: hydrocarbon chain

text: depends on

text: rotation

text: s about the 109.47°

text: tetrahedral

text: bonds of singly bonded carbon atoms.

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text: Bonding between the carbon centres is generally described in terms of bent bonds. In this model the carbon-carbon bonds are bent outwards so that the inter-orbital angle is 104°.  This reduces the level of bond strain and is achieved by distorting the sp hybridisation of carbon atoms to technically sp hybridisation (i.e.  s density and  p density) so that the C-C bonds have more π character than normal (at the same time the carbon-to-hydrogen bonds gain more s-character). One unusual consequence of bent bonding is that while the C-C bonds in cyclopropane are weaker than normal, the carbon atoms are also closer together than in a regular alkane bond: 151 pm versus 153 pm (average alkene bond: 146 pm).

text: Bonding between the carbon centres is generally described in terms of

text: bent bond

text: s. In this model the carbon-carbon bonds are bent outwards so that the inter-orbital angle is 104°.  This reduces the level of bond strain and is achieved by distorting the sp hybridisation of carbon atoms to technically sp hybridisation (i.e.  s density and  p density) so that the C-C bonds have more π character than normal (at the same time the carbon-to-hydrogen bonds gain more s-character). One unusual consequence of bent bonding is that while the C-C bonds in cyclopropane are weaker than normal, the carbon atoms are also closer together than in a regular alkane bond: 151

text: pm

text: versus 153 pm (average

text: alkene

text: bond: 146 pm).

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answers: carbon atoms

text: A nitronate (IUPAC: azinate) in organic chemistry is a functional group with the general structure NO|2|−}}.  It is the anion of a nitronic acid, a tautomeric form of a nitro compound. Just as ketones and aldehydes exist in equilibrium with their enol tautomer in basic and acidic conditions, nitro compounds exist in equilibrium under basic conditions with their nitronate tautomer. The base deprotonates the α carbon, or the carbon directly attached to the nitrogen. The nitronate has two different resonance structures, one with a negative charge on the α carbon and a double bond between the nitrogen and one of the oxygens, and another resonance structure with a double bond between the nitrogen and the α carbon, and no double bond between the nitrogen and the oxygens. A nitronic acid is also called an aci form. In the Nef reaction nitronic acids are degraded to ketones. They can be alkylated on oxygen and used as a dipole in 1,3-dipolar cycloadditions.

text: A nitronate (

text: IUPAC

text: : azinate) in

text: organic chemistry

text: is a

text: functional group

text: with the general structure NO|2|−}}.  It is the anion of a nitronic acid, a

text: tautomer

text: ic form of a

text: nitro

text: compound. Just as ketones and aldehydes exist in equilibrium with their enol tautomer in basic and acidic conditions, nitro compounds exist in equilibrium under basic conditions with their nitronate tautomer. The base deprotonates the α carbon, or the carbon directly attached to the nitrogen. The nitronate has two different resonance structures, one with a negative charge on the α carbon and a double bond between the nitrogen and one of the oxygens, and another resonance structure with a double bond between the nitrogen and the α carbon, and no double bond between the nitrogen and the oxygens. A nitronic acid is also called an aci form. In the

text: Nef reaction

text: nitronic acids are degraded to

text: ketones

text: . They can be alkylated on oxygen and used as a dipole in

text: 1,3-dipolar cycloaddition

text: s.

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text: This enzyme belongs to the family of hydrolases, those acting on carbon-nitrogen bonds other than peptide bonds, specifically in cyclic amidines.  The systematic name of this enzyme class is blasticidin-S aminohydrolase.

text: This enzyme belongs to the family of

text: hydrolase

text: s, those acting on carbon-nitrogen bonds other than peptide bonds, specifically in cyclic amidines.  The

text: systematic name

text: of this enzyme class is blasticidin-S aminohydrolase.

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text: Glycals can be formed as pyranose (six-membered) or furanose (five-membered) rings, depending on the monosaccharide used as a starting material to synthesize the glycal. Glycals can also be classified as endo-glycals or exo-glycals. A glycal is an endo-glycal when the double bond is within the ring. If the hydroxyl group on carbon 1 has been replaced with another carbon atom, a double bond can also form outside the ring between carbon 1 and this new carbon. In this case, the product is called an exo-glycal.  The glycal conformation that has been studied in most depth is that of the pyranose endo-glycal. The favoured conformation of this glycal is the half-chair, a result which has been confirmed by quantum mechanical calculations.

text: Glycals can be formed as

text: pyranose

text: (six-membered) or

text: furanose

text: (five-membered) rings, depending on the monosaccharide used as a starting material to synthesize the glycal. Glycals can also be classified as endo-glycals or exo-glycals. A glycal is an endo-glycal when the double bond is within the ring. If the hydroxyl group on carbon 1 has been replaced with another carbon atom, a double bond can also form outside the ring between carbon 1 and this new carbon. In this case, the product is called an exo-glycal.  The glycal conformation that has been studied in most depth is that of the pyranose endo-glycal. The favoured conformation of this glycal is the half-chair, a result which has been confirmed by quantum mechanical calculations.

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answers: carbon 1 has been replaced with another carbon atom

text: In 2008, he is still in prison and his health is deteriorating in Beijing No. 2 Prison. He suffers from high blood pressure and does not receive appropriate treatment. In August 2008 he sent a letter to International Olympic Committee head Jacques Rogge, decrying the conditions in Chinese prisons, which he claims to have worsened.

text: In 2008, he is still in prison and his health is deteriorating in Beijing No. 2 Prison. He suffers from high blood pressure and does not receive appropriate treatment. In August 2008 he sent a letter to

text: International Olympic Committee

text: head

text: Jacques Rogge

text: , decrying the conditions in Chinese prisons, which he claims to have worsened.

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text: In the presence of an appropriate transition metal (typically copper or rhodium ), α-diazocarbonyl compounds are converted to transition metal carbenes, which undergo addition reactions in the presence of carbon–carbon double bonds to form cyclopropanes. Insertion into carbon–carbon or carbon–hydrogen bonds is possible in substrates lacking a double bond. The intramolecular version of this reaction forms fused carbocycles, although yields of reactions mediated by copper are typically moderate. For enantioselective cyclopropanations and insertions, both copper- and rhodium-based catalysts are employed, although the latter have been more heavily studied in recent years.

text: In the presence of an appropriate

text: transition metal

text: (typically

text: copper

text: or

text: rhodium

text: α-diazocarbonyl compounds

text: are converted to

text: transition metal carbene

text: s, which undergo

text: addition reaction

text: s in the presence of carbon–carbon double bonds to form cyclopropanes. Insertion into carbon–carbon or carbon–hydrogen bonds is possible in substrates lacking a double bond. The intramolecular version of this reaction forms fused carbocycles, although yields of reactions mediated by copper are typically moderate. For

text: enantioselective

text: cyclopropanations and insertions, both copper- and rhodium-based catalysts are employed, although the latter have been more heavily studied in recent years.

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text: The greater rhea derives its scientific name from Rhea, a Greek goddess, and the Latinized form of America. It was originally described by Carl Linnaeus in his 18th-century work, Systema Naturae under the name Struthio camelus americanus. He identified specimens from Sergipe, and Rio Grande do Norte, Brazil, in 1758. They are from the family Rheidae, and the order Struthioniformes, commonly known as ratites.  They are joined in this order by emus, ostriches, cassowaries, and kiwis, along with the extinct forms moas, and elephant birds.

text: The greater rhea derives its scientific name from

text: Rhea

text: , a Greek goddess, and the Latinized form of America. It was originally described by

text: Carl Linnaeus

text: in his 18th-century work,

text: Systema Naturae

text: under the name Struthio camelus americanus. He identified specimens from

text: Sergipe

text: , and

text: Rio Grande do Norte

text: Brazil

text: , in 1758. They are from the family Rheidae, and the order

text: Struthioniformes

text: , commonly known as

text: ratite

text: s.  They are joined in this order by

text: emu

text: s,

text: ostrich

text: es,

text: cassowaries

text: , and

text: kiwi

text: s, along with the extinct forms

text: moa

text: s, and

text: elephant bird

text: s.

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text: Some of the chemical properties of activated carbon have been attributed to presence of the surface active carbon double bond.

text: Some of the chemical properties of activated carbon have been attributed to presence of the surface active carbon

text: double bond

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answers: NDQ_016399

answers: 0

answers: NDQ_016400

answers: 0

answers: NDQ_016401

answers: 0

answers: NDQ_016392

answers: carbon

answers: NDQ_016396

answers: double bond

answers: NDQ_016398

answers: hydrocarbon

answers: NDQ_016399

answers: activated carbon

answers: NDQ_016400

answers: two

answers: NDQ_016401

answers: carbon