DETAILED CONTENTS Carboxylic Acids and Nitriles 610 15 15.1 Naming Carboxylic Acids and Nitriles 611 15.2 Structure and Properties of Carboxylic Acids 613 15.3 Biological Acids and the Henderson-Hasselbalch Equation 617 15.4 Substituent Effects on Acidity 618 15.5 Preparing 15.6 Reactions of Carboxylic Acids:An Overview 62 15.7 Chemistry of Nitriles 623 15.8 Spectroscopy of Carboxylic Acids and Nitriles6 Summary 629 Summary of Reactions 630 Lagniappe-Vitamin C 631 Exercises 633 Carboxylic Acid Derivatives:Nucleophilic Acyl 16 Substitution Reactions 643 16.1 Naming Carboxylic Acid Derivatives 644 16.2 Nucleophilic Acyl Substitution Reactions 647 16.3 Nucleophilic Acyl Substitution Reactions of Carboxylic Acids 652 16.4 Chemistry of Acid Halides 659 16.5 Chemistry of Acid Anhydrides 664 16.6 Chemistry of Esters 16.7 Chemistry of Amides 67 16.8 Chemistry of Thioesters and acyl Phosphates:Biological Carboxylic acid Derivatives 674 16.9 Polyamides and Polyesters:Step-Growth Polymers 675 16.10 Spectroscopy of Carboxylic Acid Derivatives 679 Summary 680 Summary of Reactions 681 Lagniappe-B-Lactam Antibiotics6 Exercises 684 Carbonyl Alpha-Substitution and Condensation 17 Reactions 695 17.1 Keto-Enol Tautomerism6% 17.2 Reactivity of Enols:a-Substitution Reactions 699 17.3 Alpha bromination of Carboxylic acids 702 17.4 Acidity of Hydrogen Atoms:Enolate lon Formation 703 17.5 Alkylation of Enolate lons 706detailed contents xiii Carboxylic Acids and Nitriles 610 15.1 Naming Carboxylic Acids and Nitriles 611 15.2 Structure and Properties of Carboxylic Acids 613 15.3 Biological Acids and the Henderson–Hasselbalch Equation 617 15.4 Substituent Effects on Acidity 618 15.5 Preparing Carboxylic Acids 620 15.6 Reactions of Carboxylic Acids: An Overview 622 15.7 Chemistry of Nitriles 623 15.8 Spectroscopy of Carboxylic Acids and Nitriles 627 Summary 629 Summary of Reactions 630 Lagniappe—Vitamin C 631 Exercises 633 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 643 16.1 Naming Carboxylic Acid Derivatives 644 16.2 Nucleophilic Acyl Substitution Reactions 647 16.3 Nucleophilic Acyl Substitution Reactions of Carboxylic Acids 652 16.4 Chemistry of Acid Halides 659 16.5 Chemistry of Acid Anhydrides 664 16.6 Chemistry of Esters 665 16.7 Chemistry of Amides 671 16.8 Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives 674 16.9 Polyamides and Polyesters: Step-Growth Polymers 675 16.10 Spectroscopy of Carboxylic Acid Derivatives 679 Summary 680 Summary of Reactions 681 Lagniappe—-Lactam Antibiotics 683 Exercises 684 Carbonyl Alpha-Substitution and Condensation Reactions 695 17.1 Keto–Enol Tautomerism 696 17.2 Reactivity of Enols: -Substitution Reactions 699 17.3 Alpha Bromination of Carboxylic Acids 702 17.4 Acidity of Hydrogen Atoms: Enolate Ion Formation 703 17.5 Alkylation of Enolate Ions 706 15 16 17 39144_ FM_i-xxiv.indd xiii 8/26/09 10:48:50 AM