Contents xix ◆-KEY MECHANISM BOXES CHAPTER 4 Free-Radical Halogenation 130 CHAPTER 6 The S.2 Reac The SN1 Reaction The E1 Reaction 255 The E2 Reactior 262 CHAPTER7 Acid-Catalyzed Dehydration of an Alcchol 309 CHAPTER 8 Electrophilic Addition to Alkenes 324 CHAPTER 10 Grignard Reactions 439 CHAPTER 11 The Williamson Ether Synthesis 497 CHAPTER 15 The Diels-Alder Reaction 682 CHAPTER 17 Electrophilic Aromatic Substitution 752 CHAPTER 18 Nucleophilic Additions to Carbonyl Groups 833 ation of Imines 812 ation of Acetals 848 CHAPTER 20 Fischer Esterification 91 CHAPTER 21 CHAPTER 22 Base-Catalyzed Aldol Condensatic 1058 a Dehydr Aldol 1061 MECHANISM BOXES CHAPTER 6 Allylic Bromination 225 Inversion of Configuration in the SN2 Reaction 241 Racemization in the s1 reaction 248 Hydride Shift in an SN1 Reaction 250 Methyl shift in an sv1 Reaction 251 ction 258 CHAPTER 7 E2 De CHAPTER 8 lonic Addition of HX to an Alkene 327 Free-Radical Addition of HBr to Alkenes 329 Acid-Catalyzed Hydration of an Alkene 333 Oxymercuration of an Alkene 335 atonof6085oAkeneS345 Hydroboration of an alkene 340 Addition of Hald For hydrins 347 Epoxidation of Alkenes 356 Acid-Catalyzed Opening of Epoxides 357 Olefin Metathesis 372 CHAPTER 9 Metal-Ammonia Reduction of an Alkyre 404 Acid-Catalyzed Keto-Enol Tautomerism 408 Base-Catalyzed Keto-Enol Tautomerism 410CHAPTER 4 Free-Radical Halogenation 130 CHAPTER 6 The SN2 Reaction 230 The SN 1 Reaction 244 The E1 Reaction 255 The E2 Reaction 262 CHAPTER 7 Acid-Catalyzed Dehydration of an Alcohol 309 CHAPTER 8 Electrophilic Addition to Alkenes 324 CHAPTER 10 Grignard Reactions 439 CHAPTER 11 The Williamson Ether Synthesis 497 CHAPTER 15 The Diels-Aider Reaction 682 CHAPTER 17 Electrophilic Aromatic Substitution 752 CHAPTER 18 Nucleophilic Additions to Carbonyl Groups 833 Formation of lmines 842 Formation of Acetals 848 CHAPTER 20 Fischer Esterification 961 CHAPTER 21 Addition-Elimination Mechanism of Nucleophilic Acyl Substitution 997 CHAPTER 22 Base-Catalyzed Aldol Condensation 1058 Base-Catalyzed Dehydration of an Aldol 1061 The Claisen Ester Condensation 1068 CHAPTER 6 Allylic Bromination 225 Inversion of Configuration in the SN2 Reaction 241 Racemization in the SN1 Reaction 248 Hydride Shift in an SN1 Reaction 250 Methyl Shift in an SN1 Reaction 251 Rearrangement in an E1 Reaction 258 CHAPTER 7 Dehydrohalogenation by the E2 Mechanism 300 Stereochemistry of the E2 Reaction 302 E2 Debromination of a Vicinal Dibromide 306 CHAPTER 8 Ionic Addition of HX to an Alkene 327 Free-Radical Addition of HBr to Alkenes 329 Acid-Catalyzed Hydration of an Alkene 333 Oxymercuration of an Alkene 335 Hydroboration of an Alkene 340 Addition of Halogens to Alkenes 345 Formation of Halohydrins 347 Epoxidation of Alkenes 356 Acid-Catalyzed Opening of Epoxides 357 Olefin Metathesis 372 CHAPTER 9 Metal-Ammonia Reduction of an Alkyne 404 Acid-Catalyzed Keto-Enol Tautomerism 408 Base-Catalyzed Keto-Enol Tautomerism 410 Contents xix