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chapter5 - Organic Chemistry William H Brown Christopher S...

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5- 5-1 Organic Organic Chemistry Chemistry William H. Brown William H. Brown Christopher S. Foote Christopher S. Foote Brent L. Iverson Brent L. Iverson
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5- 5-2 Alkenes: Alkenes: Structure and Structure and Nomenclature Nomenclature Chapter 5 Chapter 5
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5- 5-3 Unsaturated Hydrocarbons Unsaturated Hydrocarbons Unsaturated hydrocarbon: Unsaturated hydrocarbon: contains one or more carbon-carbon double or triple bonds Alkene: Alkene: contains a carbon-carbon double bond and has the general formula C n H 2n Alkyne: Alkyne: contains a carbon-carbon triple bond and has the general formula C n H 2n-2 Ethylene (an alkene) H C C H H H Acetylene (an alkyne) . H-C C-H
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5- 5-4 Unsaturated Hydrocarbons Unsaturated Hydrocarbons Arenes: Arenes: benzene and its derivatives (Ch 21-22) we do not study arenes until Chapters 21 & 22 however, we show structural formulas of compounds containing the phenyl group before that time the phenyl group is not reactive under any of the conditions we describe in Ch 6-20 Benzene Alternative representations       for the phenyl  group C C C C C C C 6 H 5 - Ph- H H H H H H
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5- 5-5 Structure of Alkenes Structure of Alkenes A double bond consists of one sigma bond formed by the overlap of sp 2 hybrid orbitals and one pi bond formed by the overlap of parallel 2 p orbitals the two carbon atoms of a double bond and the four atoms bonded to them lie in a plane, with bond angles of approximately 120°
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5- 5-6 Structure of Alkenes Structure of Alkenes it takes approximately 264 kJ (63 kcal)/mol to break the pi bond in ethylene; that is, to rotate one carbon by 90° with respect to the other so that there is no overlap between 2 p orbitals on adjacent carbons
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5- 5-7 Cis,Trans Cis,Trans Isomerism in Alkenes Isomerism in Alkenes Cis,trans Cis,trans isomers: isomers: isomers that have the same connectivity but a different arrangement of their atoms in space due to the presence of either a ring or a carbon-carbon double bond cis- 2-Butene mp -139 C, bp 4 C trans- 2-Butene mp -106 C, bp 1 C C C CH 3 H H 3 C H C C H CH 3 H 3 C H
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5- 5-8 Index of Hydrogen Deficiency Index of Hydrogen Deficiency Index of hydrogen deficiency (IHD): Index of hydrogen deficiency (IHD): the sum of the number of rings and pi bonds in a molecule To determine IHD, compare the number of hydrogens in an unknown compound with the number in a reference hydrocarbon of the same number of carbons and with no rings or pi bonds the molecular formula of the reference hydrocarbon is C n H 2n+2
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