Contents XV 19-8 Amine Salts as Phase-Transfer Catalysts 884 19-9 Sn 19-10 Reactions of Amines with Ketones and Aldehydes (Review)890 19.11 Aromatic Substitution of Arylamines and Pyridine 890 19.12 Alkylation of Amines by alkyl Halides 894 19.13 Acylation of Amines by Acid Chlorides 895 19-14 Formation of Sulfonamides 897 19-15 Amines as Leaving Groups:The Hofmann Elimination 898 19-16 Oxidation of Amines:The Cope Elimination 902 1917 Reactions of Amines with Nitrous Acid 904 19-18 906 by 19-21 Acylati 916 Of A 923 Chapter 19 Glossary 925 Study Problems 928 20 CARBOXYLIC ACIDS 937 20-1 Introduction 937 20-2 Nomenclature of Carboxvlic Acids 937 203 Cab Salts of Car oxylie Acids 946 Spectroscopy of Carb Synthe mmary:S c Acids 957 20.9 20-10 Condensation of Acids with Alcohols:The Fischer Esterification 960 Key Mechanism:Fischer Esterification 961 20-11 Esterification Using Diazomethane 964 20-12 Condensation of Acids with Amin 96 nd Us of Acid Ch Acids970 972 s973 21 CARBOXYLIC ACID DERIVATIVES 980 21-1 Introduction 980 21-2 Structure and Nomenclature of Acid Derivatives 981 21-3 Physical Properties of Carboxylic Acid Derivatives 987 21-4 Spectroscopy of Carboxylic Acid Derivatives 98919-8 Amine Salts as Phase-Transfer Catalysts 884 19-9 Spectroscopy of Amines 886 19-10 Reactions of Amines with Ketones and Aldehydes (Review) 890 19-11 Aromatic Substitution of Arylamines and Pyridine 890 19-12 Alkylation of Amines by Alkyl Halides 894 19-13 Acylation of Amines by Acid Chlorides 895 19-14 Formation of Sulfonamides 897 19-15 Amines as Leaving Groups: The Hofmann Elimination 898 19-16 Oxidation of Amines; The Cope Elimination 902 19-17 Reactions of Amines with Nitrous Acid 904 19-18 Reactions of Arenediazonium Salts 906 Summary: Reactions of Amines 910 19-19 Synthesis of Amines by Reductive Amination 912 19-20 Synthesis of Amines by Acylation-Reduction 915 19-21 Syntheses Limited to Primary Amines 916 Summary: Synthesis of Amines 923 Chapter 19 Glossary 925 Study Problems 928 20 CARBOXYLIC ACIDS 937 20-1 Introduction 937 20-2 Nomenclature of Carboxylic Acids 937 20-3 Structure and Physical Properties of Carboxylic Acids 941 20-4 Acidity of Carboxylic Acids 942 20-5 Salts of Carboxylic Acids 946 20-6 Commercial Sources of Carboxylic Acids 949 20-7 Spectroscopy of Carboxylic Acids 950 20-8 Synthesis of Carboxylic Acids 954 Summary: Syntheses of Carboxylic Acids 957 20-9 Reactions of Carboxylic Acids and Derivatives; Nucleophilic Acyl Substitution 958 20-10 Condensation of Acids with Alcohols: The Fischer Esterification 960 Key Mechanism: Fischer Esterification 961 20-11 Esterification Using Diazomethane 964 20-12 Condensation of Acids with Amines: Direct Synthesis of Amides 965 20-13 Reduction of Carboxylic Acids 965 20-14 Alkylation of Carboxylic Acids to Form Ketones 967 20-15 Synthesis and Use of Acid Chlorides 968 Summary: Reactions of Carboxylic Acids 970 Chapter 20 Glossary 972 Study Problems 973 21 CARBOXYLIC ACID DERIVATIVES 980 21-1 Introduction 980 21-2 Structure and Nomenclature of Acid Derivatives 981 21-3 Physical Properties of Carboxylic Acid Derivatives 987 21-4 Spectroscopy of Carboxylic Acid Derivatives 989 Contents xv