Contents 6-18 Positional Orientation of elimination:Zaitsey's rule 260 6-19 Second-Order Elimination:The E2 Reaction 261 Key Mechanism:The E2 Reaction 262 6-20 Stereochemistry of the E2 Reaction 264 6-21 Comparison of El and E2 Elimination Mechanisms 265 Summary:Elimination Reactions 267 Problem-Solving Strategy:Predic ting Substitutions and Eliminations 267 Summary:Reactions of Alkyl Halides 270 6w27632 7 STRUCTURE AND SYNTHESIS OF ALKENES 281 7-1 Introduction The Orbital Description of the Alkene Double Bond 282 7.5 287 7.6 e of Alkenes 290 7-7 Stability of Alkenes 292 7-8 Physical Properties of Alkenes 298 7-9 Alkene Synthesis by Elimination of Alkyl Halides 300 7-10 Alkene Synthesis by Dehydration of Alcohols 308 ed-Catalyed 7-11 by Hig h-Temperrd Sum ds for nthesis of Alkenes 316 Chanter Glos ary 317 Study Problems 319 8REACTIONS OF ALKENES 323 to Al Key Mechanism:Electrophilic Addition to Alkenes 324 8-3 Addition of Hydrogen Halides to Alkenes 326 8-4 Addition of Water:Hydration of Alkenes 332 8-5 Hydration by Oxymercuration-Demercuration 335 8-6 Alkoxymercuration-Demercuration 337 8-1 Hydroboration of Alkenes 338 8-8 Addition of Ha ogens to Alk es344 8-9 Formation of Halohydrins 347 8-10 Catalytic Hydrogenationo enes to A cnes 352 des 357 9 15 Oxidati ylation 8-16 365 8-17 Olefin Metathesis 3696-18 Positional Orientation of Elimination: Zaitsev's Rule 260 6-19 Second-Order Elimination: The E2 Reaction 261 Key Mechanism: The E2 Reaction 262 6-20 Stereochemistry of the E2 Reaction 264 6-21 Comparison of E1 and E2 Elimination Mechanisms 265 Summary: Elimination Reactions 267 Problem-Solving Strategy: Predicting Substitutions and Eliminations 267 Summary: Reactions of Alkyl Halides 270 Chapter 6 Glossary 273 Study Problems 276 7 STRUCTURE AND SYNTHESIS OF ALKENES 281 7-1 Introduction 281 7-2 The Orbital Description of the Alkene Double Bond 282 7-3 Elements of Unsaturation 283 7-4 Nomenclature of Alkenes 285 7-5 Nomenclature of Cis-Trans Isomers 287 Summary: Rules for Naming Alkenes 289 7-6 Commercial Importance of Alkenes 290 7-7 Stability of Alkenes 292 7-8 Physical Properties of Alkenes 298 7-9 Alkene Synthesis by Elimination of Alkyl Halides 300 7-10 Alkene Synthesis by Dehydration of Alcohols 308 Key Mechanism: Acid-Catalyzed Dehydration of an Alcohol 309 7-11 Alkene Synthesis by High-Temperature Industrial Methods 311 Problem-Solving Strategy: Proposing Reaction Mechanisms 312 Summary: Methods for Synthesis of Alkenes 316 Chapter 7 Glossary 317 Study Problems 319 8 REACTIONS OF ALKENES 323 8-1 Reactivity of the Carbon-Carbon Double Bond 323 8-2 Electrophilic Addition to Alkenes 324 Key Mechanism: Electrophilic Addition to Alkenes 324 8-3 Addition of Hydrogen Halides to Alkenes 326 8-4 Addition of Water: Hydration of Alkenes 332 8-5 Hydration by Oxymercuration-Demercuration 335 8-6 Alkoxymercuration-Demercuration 337 8-7 Hydroboration of Alkenes 338 8-8 Addition of Halogens to Alkenes 344 8-9 Formation of Halohydrins 347 8-10 Catalytic Hydrogenation of Alkenes 350 8-11 Addition of Carbenes to Alkenes 352 8-12 Epoxidation of Alkenes 355 8-13 Acid-Catalyzed Opening of Epoxides 357 8-14 Syn Hydroxylation of Alkenes 360 8-15 Oxidative Cleavage of Alkenes 362 8-16 Polymerization of Alkenes 365 8-17 Olefin Metathesis 369 Contents ix