CONTENTS 5 Carboxylic Acids and Nitriles 530 15.1 Naming Carboxylic Acids and Nitriles 5 15-2 Structure and Properties of Carboxylic Acids 533 153 Biological Acids and the Henderson-Hasselbalch Equation 154 Substituent Effects on Acidity 15-5 Preparing Carboxylic Acids 540 15-6 Reactions of Carboxylic Acids:An Overview 15-7 Chemistry of Nitriles 543 15-8 Spectroscopy of Carboxylic Acids and Nitriles 5 SOMETHING EXTRA Vitamin C 50 16 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 555 16-1 Naming Carboxylic Acid Derivatives 16-2 Nucleophilic Acyl Substitution Reactions 59 16-3 Reactions of Carboxylic Acids 16-4 Reactions of Acid Halides 90 16-5 Reactions of Acid Anhydrides 576 16-6 Reactions of Esters 167 Reactions of Amides 16-8 Reactions of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives 587 16-9 Polyamides and Polyesters:Step-Growth Polymers 589 16-10 Spectroscopy of Carboxylic Acid Derivatives 592 SOMETHING EXTRA B-Lactam Antibiotics 594 Carbonyl Alpha-Substitution and Condensation Reactions599 17-1 Keto-Enol Tautomerism %6 17-2 Reactivity of Enols:a-Substitution Reactions 6 17-3 Alpha Bromination of Carboxylic Acids 17-4 Acidity of a Hydrogen Atoms:Enolate lon Formation 607Contents xiii 15 Carboxylic acids and nitriles | 530 15-1 naming carboxylic acids and nitriles 531 15-2 structure and properties of carboxylic acids 533 15-3 Biological acids and the henderson–hasselbalch Equation 537 15-4 substituent Effects on acidity 538 15-5 preparing carboxylic acids 540 15-6 Reactions of carboxylic acids: an overview 543 15-7 chemistry of nitriles 543 15-8 spectroscopy of carboxylic acids and nitriles 548 soMetHinG eXtra Vitamin c 550 16 Carboxylic acid Derivatives: nucleophilic acyl substitution reactions | 555 16-1 naming carboxylic acid Derivatives 556 16-2 nucleophilic acyl substitution Reactions 559 16-3 Reactions of carboxylic acids 564 16-4 Reactions of acid halides 570 16-5 Reactions of acid anhydrides 576 16-6 Reactions of Esters 578 16-7 Reactions of amides 584 16-8 Reactions of thioesters and acyl phosphates: Biological carboxylic acid Derivatives 587 16-9 polyamides and polyesters: step-growth polymers 589 16-10 spectroscopy of carboxylic acid Derivatives 592 soMetHinG eXtra b-lactam antibiotics 594 17 Carbonyl alpha-substitution and Condensation reactions | 599 17-1 Keto–Enol tautomerism 600 17-2 Reactivity of Enols: a-substitution Reactions 603 17-3 alpha Bromination of carboxylic acids 606 17-4 acidity of a hydrogen atoms: Enolate ion Formation 607 42912_00_FM_i-xxiv.indd 13 1/16/14 3:00 PM Copyright 2015 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it