DETAILED CONTENTS 7.6 Electrophilic Addition Reactions of Alkenes 27 Writing Organic Reactions 229 Orientation of Electrophilic Addition:Markovnikov's Rule 230 Carbocation Structure and Stability 233 7.9 The Hammond Postulate 235 7.10 Evidence for the Mechanism of Electrophilic Additions:Carbocation Rearrangements 238 Summary 241 Lagniappe-Terpenes:Naturally Occurring Alkenes 242 Exercises 243 Reactions of Alkenes and Alkynes 251 8 8.1 Preparing Alkenes:A Preview of Elimination Reactions 252 8.2 Halogenation of Alkenes 254 8.3 Halohydrins from Alkenes 26 8.4 Hydration of Alk kenes 257 Reduction of Alkenes:Hydrogenation 261 8.6 Oxidation of Alkenes:Epoxidation 265 Oxidation of Alkenes:Hydroxylation 8.8 Oxidation of Alkenes:Cleavage to Carbonyl Compounds 270 8.9 Addition of Carbenes to Alkenes:Cyclopropane Synthesis 272 8.10 Radical additions to alkenes:alkene polyr mers 274 8.11 Biological Additions of Radicals to Alkenes 27 8.12 Conjugated Dienes 279 8.13 Reactions of Coniugated dienes 283 The Diels-Alder Cycloaddition Reaction 285 Reactions of Alkynes290 Summary 293 Leaming Reactions2 Summary of Reactions 295 Lagniappe-Natural Rubber29 Exercises 299 Aromatic Compounds 309 9 9.1 Naming Aromatic Compounds 310 9.2 Structure and Stability of Benzene 313 9.3 Aromaticity and the Huckel 4n+2 Rule 315 94 Aromatic lons and Aromatic Heterocycles 317 .5 Polycyclic Aromatic Compounds 322 9.6 Reactions of Aromatic Compounds:Electrophilic Substitution 324detailed contents ix 7.6 Electrophilic Addition Reactions of Alkenes 227 Writing Organic Reactions 229 7.7 Orientation of Electrophilic Addition: Markovnikov’s Rule 230 7.8 Carbocation Structure and Stability 233 7.9 The Hammond Postulate 235 7.10 Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements 238 Summary 241 Lagniappe—Terpenes: Naturally Occurring Alkenes 242 Exercises 243 Reactions of Alkenes and Alkynes 251 8.1 Preparing Alkenes: A Preview of Elimination Reactions 252 8.2 Halogenation of Alkenes 254 8.3 Halohydrins from Alkenes 256 8.4 Hydration of Alkenes 257 8.5 Reduction of Alkenes: Hydrogenation 261 8.6 Oxidation of Alkenes: Epoxidation 265 8.7 Oxidation of Alkenes: Hydroxylation 267 8.8 Oxidation of Alkenes: Cleavage to Carbonyl Compounds 270 8.9 Addition of Carbenes to Alkenes: Cyclopropane Synthesis 272 8.10 Radical Additions to Alkenes: Alkene Polymers 274 8.11 Biological Additions of Radicals to Alkenes 278 8.12 Conjugated Dienes 279 8.13 Reactions of Conjugated Dienes 283 8.14 The Diels–Alder Cycloaddition Reaction 285 8.15 Reactions of Alkynes 290 Summary 293 Learning Reactions 294 Summary of Reactions 295 Lagniappe—Natural Rubber 298 Exercises 299 Aromatic Compounds 309 9.1 Naming Aromatic Compounds 310 9.2 Structure and Stability of Benzene 313 9.3 Aromaticity and the Hückel 4n 2 Rule 315 9.4 Aromatic Ions and Aromatic Heterocycles 317 9.5 Polycyclic Aromatic Compounds 322 9.6 Reactions of Aromatic Compounds: Electrophilic Substitution 324 8 9 39144_ FM_i-xxiv.indd ix 8/26/09 10:48:49 AM