Contents 18-14 Mermatio sm on of Cyanohydrins 849 18-15 0850 85 ormation of Imines85 18-16 mine 853 and Aldehydes 854 18-17 Formation of Acetals 855 Key Mechanism 18-6:Formation of Acetals 856 roblem-Solving Strategy:Proposing Re action Mechanisms 858 18-18 ng Groups 860 1828 ehydes 86 echanis 862 shner Red 86os of Ketones and A h86 lehydes 865 Study proble ms870 19 AMINES 879 19- Introduction 879 - e of Ami 880 19 Str ture e of A ys Amines 884 ty c 19.2 Effec m 896 city 887 Salts of Ar 19-8 19.9 actio p of Amines 891 19-10 ones and Aldehydes(Review)895 atic Substitut of Ar Mechanism 19-1:Electrophilic Ard atic S of Pyridine 897 nism-2:Nucleophilic Aromatic Substitution 19-11 A 19.12 es by Alkyl Halides Acid Chlo 900 19.2.A e by an Acid Chloride 901 19.12 19-14 Amines as Leaving Gro os:The Hofmann elimination 904 Mechanism 19-4:Hofmann Elimination 904 19-15 Oxidation of Amines:The cope Elimination 907 Mechanism 19-5:The Cope Elimination of an Amine Oxide 908 19-16 Reactions of amines with nitrous acid 910 Mechanism 19-6:Diazotization of an Amine 910 19-17 Reactions of Arenediazonium Salts 911 Summary:Reactions of Amines 915 19-18 Synthesis of Amines by Reductive Amination 918 19-19 Synthesis of Amines by Acylation-Reduction 920Contents xv 18-14 Formation of Cyanohydrins 849 Mechanism 18-4: Formation of Cyanohydrins 849 18-15 Formation of Imines 850 Key Mechanism 18-5: Formation of Imines 851 18-16 Condensations with Hydroxylamine and Hydrazines 853 Summary: Condensations of Amines with Ketones and Aldehydes 854 18-17 Formation of Acetals 855 Key Mechanism 18-6: Formation of Acetals 856 Problem-Solving Strategy: Proposing Reaction Mechanisms 858 18-18 Use of Acetals as Protecting Groups 860 18-19 Oxidation of Aldehydes 861 18-20 Reductions of Ketones and Aldehydes 862 Mechanism 18-7: Wolff–Kishner Reduction 864 Summary: Reactions of Ketones and Aldehydes 865 Essential Terms 868 Study Problems 870 19 AMINES 879 19-1 Introduction 879 19-2 Nomenclature of Amines 880 19-3 Structure of Amines 882 19-4 Physical Properties of Amines 884 19-5 Basicity of Amines 886 19-6 Effects on Amine Basicity 887 19-7 Salts of Amines 889 19-8 Spectroscopy of Amines 891 19-9 Reactions of Amines with Ketones and Aldehydes (Review) 895 19-10 Aromatic Substitution of Arylamines and Pyridine 896 Mechanism 19-1: Electrophilic Aromatic Substitution of Pyridine 897 Mechanism 19-2: Nucleophilic Aromatic Substitution of Pyridine 899 19-11 Alkylation of Amines by Alkyl Halides 899 19-12 Acylation of Amines by Acid Chlorides 900 Mechanism 19-3: Acylation of an Amine by an Acid Chloride 901 19-13 Formation of Sulfonamides 903 19-14 Amines as Leaving Groups: The Hofmann Elimination 904 Mechanism 19-4: Hofmann Elimination 904 19-15 Oxidation of Amines; The Cope Elimination 907 Mechanism 19-5: The Cope Elimination of an Amine Oxide 908 19-16 Reactions of Amines with Nitrous Acid 910 Mechanism 19-6: Diazotization of an Amine 910 19-17 Reactions of Arenediazonium Salts 911 Summary: Reactions of Amines 915 19-18 Synthesis of Amines by Reductive Amination 918 19-19 Synthesis of Amines by Acylation–Reduction 920