xiv Contents 20.17 Synthesis 759 Key Concepts 762 Problems 765 21 Aldehydes and Ketones. -Nucleophilic Addition 774 ature 776 779 780 Interesting Aldehydes and Ketones 783 21.6 Preparation of Aldehydes and Ketones 784 21.7 Reactions of Aldehydes and Ketones-General Considerations 785 21.8 Nucleophilic Addition of H-and R--A Review 789 21.9 Nucleophilic Addition of-CN 790 21.10 The Wittig Reaction 792 21.11 Addition of 1 Amines 797 21.12 Addition of 2 Amines 800 21.13 Addition of HO- 802 21.14 Addition of Alcohols ation 804 oups An Introduction to Carbohydrates 812 Key Concepts 813 Problems 815 22 Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution 825 Structure and Bor 22.4 Physical Properties 834 22.5 Spectroscopic Properties 835 22.6 Interesting esters and amides 836 22.7 Introduction to Nucleophilic Acyl Substitution 838 22.8 Reactions of acid chlorides 842 22.9 Reactions of Anhydrides 844 22.10 Reactions of Carboxylic Acids 845 22 11 Reactions of Esters 850 2212A olysis 85 ons R55 22公A。Summsry st Nussphie AsyI SubN23a Applica ion nism of Action of B-Lactam Antibiotics 85 22.16 Natural and Synthetic Fibers 858 22.17 Biological Acylation Reactions 860 22.18 Nitriles 862 Key Concepts 867 Problems 870 xiv Contents 20.17 Synthesis 759 Key Concepts 762 Problems 765 21 Aldehydes and Ketones—Nucleophilic Addition 774 21.1 Introduction 775 21.2 Nomenclature 776 21.3 Physical Properties 779 21.4 Spectroscopic Properties 780 21.5 Interesting Aldehydes and Ketones 783 21.6 Preparation of Aldehydes and Ketones 784 21.7 Reactions of Aldehydes and Ketones—General Considerations 785 21.8 Nucleophilic Addition of H– and R– —A Review 789 21.9 Nucleophilic Addition of – CN 790 21.10 The Wittig Reaction 792 21.11 Addition of 1° Amines 797 21.12 Addition of 2° Amines 800 21.13 Addition of H2O—Hydration 802 21.14 Addition of Alcohols—Acetal Formation 804 21.15 Acetals as Protecting Groups 808 21.16 Cyclic Hemiacetals 809 21.17 An Introduction to Carbohydrates 812 Key Concepts 813 Problems 815 22 Carboxylic Acids and Their Derivatives— Nucleophilic Acyl Substitution 825 22.1 Introduction 826 22.2 Structure and Bonding 828 22.3 Nomenclature 830 22.4 Physical Properties 834 22.5 Spectroscopic Properties 835 22.6 Interesting Esters and Amides 836 22.7 Introduction to Nucleophilic Acyl Substitution 838 22.8 Reactions of Acid Chlorides 842 22.9 Reactions of Anhydrides 844 22.10 Reactions of Carboxylic Acids 845 22.11 Reactions of Esters 850 22.12 Application: Lipid Hydrolysis 853 22.13 Reactions of Amides 855 22.14 Application: The Mechanism of Action of β-Lactam Antibiotics 856 22.15 Summary of Nucleophilic Acyl Substitution Reactions 857 22.16 Natural and Synthetic Fibers 858 22.17 Biological Acylation Reactions 860 22.18 Nitriles 862 Key Concepts 867 Problems 870 smi75625_fm_00i-xxxiv.indd xiv 11/17/09 11:21:32 AM