xiv Contents 17-13 Addition Reactions of Benzene Derivatives 787 17-14 Side-Chain Reactions of Benzene Derivatives 789 17-15 Reactions of Phenols 793 Summary:Reactions of Aromatic Compounds 796 Chapter 17 Glossary 799 Study Problems 802 18 KETONES AND ALDEHYDES 807 18-1 Carbonyl Compounds 807 18-2 Structure of the Carbonyl Group 808 18-3 Nomenclature of Ketones and Aldehydes 808 18-4 Physical Properties of Ketones and Aldehydes 811 185 Spectroscopy of Ketones and Aldehydes 813 18-6 Industrial Importance of Ketones and Aldehydes 820 18-7 Review of Syntheses of Ketones and Aldehydes 820 8- Synthesis of Ketones Alde from N 1保12 nd Ald d Addition 831 oups 833 18-13 The Wintig Beaction 834 18-14 Hvdration of Ketones and Aldehydes 838 18.15 Formation of Cvanohydrins 840 18-16 Formation of Imines 842 Key Mechanism:Formation of Imines 842 18-17 Condensations with Hydroxylamine and Hydrazines 845 Summary:Condensations of Amines with Ketones and Aldehydes 846 18-18 Formation of Acetals 847 18.10 Use of Ac eaction Mechanisms 850 18-20 18-21 Reductions of Keto nes and Aldehydes 854 Summary:Reactions of Ketones and Aldehydes 857 Chapter 18 Glossary 860 Study Problems 863 19 AMINES 872 19-1 Introduction 872 19-2 Nomenclature of Amines 873 19-3 Structure of Amines 875 19-4 Physical Properties of Amines 877 19-5 Basicity of Amines 879 199 Effects on Amine Basicity 880 Salts of Amines 882 xiv Contents 17-13 Addition Reactions of Benzene Derivatives 787 17-14 Side-Chain Reactions of Benzene Derivatives 789 17-15 Reactions of Phenols 793 Summary: Reactions of Aromatic Compounds 796 Chapter 17 Glossary 799 Study Problems 802 18 KETONES AND ALDEHYDES 807 18-1 Carbonyl Compounds 807 18-2 Structure of the Carbonyl Group 808 18-3 Nomenclature of Ketones and Aldehydes 808 18-4 Physical Properties of Ketones and Aldehydes 811 18-5 Spectroscopy of Ketones and Aldehydes 813 18-6 Industrial Importance of Ketones and Aldehydes 820 18-7 Review of Syntheses of Ketones and Aldehydes 820 18-8 Synthesis of Ketones and Aldehydes Using 1,3-Dithianes 824 18-9 Synthesis of Ketones from Carboxylic Acids 825 18-10 Synthesis of Ketones from Nitriles 826 18-11 Synthesis of Aldehydes and Ketones from Acid Chlorides 827 Summary: Syntheses of Ketones and Aldehydes 828 18-12 Reactions of Ketones and Aldehydes: Nucleophilic Addition 831 Key Mechanism: Nucleophilic Additions to Carbonyl Groups 833 18-13 The Wittig Reaction 834 18-14 Hydration of Ketones and Aldehydes 838 18-15 Formation of Cyanohydrins 840 18-16 Formation oflmines 842 Key Mechanism: Formation of lmines 842 18-17 Condensations with Hydroxylamine and Hydrazines 845 Summary: Condensations of Arnines with Ketones and Aldehydes 846 18-18 Formation of Acetals 84 7 Key Mechanism: Formation of Acetals 848 Problem-Solving Strategy: Proposing Reaction Mechanisms 850 18-19 Use of Acetals as Protecting Groups 852 18-20 Oxidation of Aldehydes 854 18-21 Reductions of Ketones and Aldehydes 854 Summary: Reactions of Ketones and Aldehydes 857 Chapter 18 Glossary 860 Study Problems 863 19 AMINES 872 19-1 Introduction 872 19-2 Nomenclature of Amines 873 19-3 Structure of Amines 875 19-4 Physical Properties of Amines 877 19-5 Basicity of Amines 879 19-6 Effects on Amine Basicity 880 19-7 Salts of Amines 882