xvi Contents 21-5 Interconversion of Acid Derivatives by Nucleophilic Acyl n996 Mechanism 21-6 Transesterification 1005 Problem-Solving Strategy:Proposing Reaction Mechanisms 1006 21-7 Hydrolysis of Carboxylic Acid Derivatives 1008 21-8 Reduction of Acid Derivatives 1013 21-9 Reactions of Ac Derivativeswith Organometallic 3110 Sumn 31.11 21.12 Summary of the Che 21.13 Summary ofthe chemistry of Amides 1024 21-14 Summary of the Chemistry of Nitriles 1027 21.15 Thioesters 1028 21-16 Esters and Amides of Car bonic Acid 1030 Chapter 21 Glossary 1032 Study Problems 1034 CONDENSATIONS AND ALPHA SUBSTITUTIONS 22 OF CARBONYL COMPOUNDS 1043 22.3 Ion 104g 22.4 mines 1049 33.5 Alpha Halog es1052 126 a Bromination of Acids:The HVZ Reaction 1057 22-7 The Aldol Condensation of Ketones and Aldehydes 1057 Key Mechanism:Base-Catalyzed Aldol Condensation 1058 22-8 Dehydration of Aldol Products 1061 Key Mechanism:Base-Catalyzed Dehydration of an Aldol 1061 22-9 Cros sed Aldol Condensations 1062 ng S ons 2212 ng Sy sing Aldol Condensations106 Co 1067 Key Mechanism:The Cla Ester Condensation 1068 The Dieckm ann cond Crossed Claisen Condensations 1071 22.15 Syntheses Using B-Dicarbonyl Compounds 1074 22.16 The Malonic Ester Synthesis 1076 22.17 The Acetoacetic Ester Synthesis 1079 22-18 Conjugate Additions:The Michael Reaction 1081 22.19 The Robinson Annulation 1085 robm-Soving Strategy:Proposing Reaction Summary:Enolate Additions and Condensations 1088 Chapter 22 Glossary 1090 Study Problems 1092 xvi Contents 21-5 Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution 996 Key Mechanism: Addition-Elimination Mechanism of Nucleophilic Acyl Substitution 997 21-6 Transesterification 1005 Problem-Solving Strategy: Proposing Reaction Mechanisms 1006 21-7 Hydrolysis of Carboxylic Acid Derivatives I 008 21-8 Reduction of Acid Derivatives 1013 21-9 Reactions of Acid Derivatives with Organometallic Reagents 1015 21-10 Summary of the Chemistry of Acid Chlorides 1017 21-11 Summary of the Chemistry of Anhydrides 1018 21-12 Summary of the Chemistry of Esters 1021 21-13 Summary of the Chemistry of Amides 1024 21-14 Summary of the Chemistry of Nitriles 1027 21-15 Thioesters 1028 21-16 Esters and Amides of Carbonic Acid 1030 Chapter 21 Glossary 1032 Study Problems 1034 CONDENSATIONS AND ALPHA SUBSTITUTIONS 22 OF CARBONYL COMPOUNDS 1043 22-1 Introduction 1043 22-2 Enols and Enolate Ions 1044 22-3 Alkylation of Enol ate Ions 1048 22-4 Formation and Alkylation of Enamines 1049 22-5 Alpha Halogenation of Ketones 1052 22-6 a Bromination of Acids: The HVZ Reaction 1057 22-7 The Aldol Condensation of Ketones and Aldehydes 1057 Key Mechanism: Base-Catalyzed Aldol Condensation 1 058 22-8 Dehydration of Aldol Products 1061 Key Mechanism: Base-Catalyzed Dehydration of an Aldol 1 061 22-9 Crossed Aldol Condensations 1062 Problem-Solving Strategy: Proposing Reaction Mechanisms 1063 22-10 Aldol Cyclizations 1065 22-11 Planning Syntheses Using Aldol Condensations 1066 22-12 The Claisen Ester Condensation 1067 Key Mechanism: The Claisen Ester Condensation 1068 22-13 The Dieckmann Condensation: A Claisen Cyclization 1070 22-14 Crossed Claisen Condensations 1071 22-15 Syntheses Using {3-Dicarbonyl Compounds 1074 22-16 The Malonic Ester Synthesis 1076 22-17 The Acetoacetic Ester Synthesis 1079 22-18 Conjugate Additions: The Michael Reaction 1081 22-19 The Robinson Annulation 1085 Problem-Solving Strategy: Proposing Reaction Mechanisms 1086 Summary: Enolate Additions and Condensations 1088 Chapter 22 Glossary 1090 Study Problems 1092