CONTENTS 7-10 Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements 206 SOMETHING EXTRA Terpenes:Naturally Occurring Alkenes 209 8 Reactions of Alkenes and Alkynes 212 8-1 Preparing Alkenes:A Preview of Elimination Reactions 213 8-2 Halogenation of Alkenes 214 8-3 Halohydrins from Alkenes 84 Hydration of Alkenes 218 8-5 Reduction of Alkenes:Hydrogenation 2 8-6 Oxidation of Alkenes:Epoxidation 27 Oxidation of Alkenes:Hydroxylation 2 8-8 Oxidation of Alkenes:Cleavage to Carbonyl Compounds 231 8.9 Addition of Carbenes to Alkenes:Cyclopropane Synthesis 233 8.10 Radical Additions to Alkenes:Chain-Growth Polymers 235 811 Biological Additions of Radicals to Alkenes 240 8.12 Conjugated Dienes 241 8-13 Reactions of Conjugated Dienes 245 8-14 The Diels-Alder Cycloaddition Reactior 8-15 Reactions of Alkynes 253 SOMETHING EXTRA Natural Rubber 258 Learning Reactions 261 9 Aromatic Compounds 265 91 Naming Aromatic Compounds 266 9 Structure and Stability of Benzene 268 Aromaticity and the Huckel 4n +2 Rule 272 94 Aromatic lons and Aromatic Heterocycles 274 95 Polycyclic Aromatic Compounds 279 9-6 Reactions of Aromatic Compounds:Electrophilic Substitution 97 Alkylation and Acylation of Aromatic Rings The Friedel-Crafts Reaction 289 9-8 Substituent Effects in Electrophilic Substitutions 295Contents ix 7-10 Evidence for the Mechanism of Electrophilic additions: carbocation Rearrangements 206 soMetHinG eXtra terpenes: naturally occurring alkenes 209 8 reactions of alkenes and alkynes | 212 8-1 preparing alkenes: a preview of Elimination Reactions 213 8-2 halogenation of alkenes 214 8-3 halohydrins from alkenes 217 8-4 hydration of alkenes 218 8-5 Reduction of alkenes: hydrogenation 223 8-6 oxidation of alkenes: Epoxidation 227 8-7 oxidation of alkenes: hydroxylation 229 8-8 oxidation of alkenes: cleavage to carbonyl compounds 231 8-9 addition of carbenes to alkenes: cyclopropane synthesis 233 8-10 Radical additions to alkenes: chain-growth polymers 235 8-11 Biological additions of Radicals to alkenes 240 8-12 conjugated Dienes 241 8-13 Reactions of conjugated Dienes 245 8-14 the Diels–alder cycloaddition Reaction 247 8-15 Reactions of alkynes 253 soMetHinG eXtra natural Rubber 258 learning Reactions 261 9 aromatic Compounds | 265 9-1 naming aromatic compounds 266 9-2 structure and stability of Benzene 268 9-3 aromaticity and the hückel 4n 1 2 Rule 272 9-4 aromatic ions and aromatic heterocycles 274 9-5 polycyclic aromatic compounds 279 9-6 Reactions of aromatic compounds: Electrophilic substitution 281 9-7 alkylation and acylation of aromatic Rings: the Friedel–crafts Reaction 289 9-8 substituent Effects in Electrophilic substitutions 295 42912_00_FM_i-xxiv.indd 9 1/16/14 3:00 PM Copyright 2015 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it