DETAILED CONTENTS 13.7 Preparation and Reactions of Thiols 526 138 Ethers and Sulfides 528 13.9 Preparing Ethers 529 13.10 Reactions of Ethers 531 13.11 Preparation and Reactions of Sulfides 534 13.12 Ethers Summary 538 Summary of Reactions 539 Lagniappe-Ethanol:Chemical,Drug,and Poison 542 Exercises 543 Preview of Carbonyl Chemistry sss W General Reactions of Carbonyl Compounds 557 IV Summary 562 Exercises 563 14 Aldehydes and Ketones:Nucleophilic Addition Reactions 564 14.1 Naming Aldehydes and Ketones 565 14.2 Preparing Aldehydes and Ketones 567 14.3 Oxidation of Aldehydes56 14.4 Nucleophilic Addition Reactions of Aldehydes and Ketones 569 14.5 Nucleophilic Addition of H2O:Hydration 572 14.6 Nucleophilic Addition of Grignard and Hydride Reagents: Alcohol Formation 574 14.7 Nucleophilic Addition of Amines:Imine and Enamine Formation 576 14.8 Nucleophilic Addition ofAlcohols:Acetal Formation 580 14.9 Nucleophilic Addition of Phosphorus Ylides:The Wittig Reaction5 14.10 Biological Reductions 587 14.11 Conjugate Nucleophilic Addition to a,B-Unsaturated Aldehydes and Ketones 14.12 Spectroscopy of Aldehydes and Ketones 593 Summary 596 Summary of Reactions 597 Lagniappe-Enantioselective Synthesis599 Exercises 600 xii detailed contents 13.7 Preparation and Reactions of Thiols 526 13.8 Ethers and Sulfides 528 13.9 Preparing Ethers 529 13.10 Reactions of Ethers 531 13.11 Preparation and Reactions of Sulfides 534 13.12 Spectroscopy of Alcohols, Phenols, and Ethers 536 Summary 538 Summary of Reactions 539 Lagniappe—Ethanol: Chemical, Drug, and Poison 542 Exercises 543 Preview of Carbonyl Chemistry 555 I Kinds of Carbonyl Compounds 555 II Nature of the Carbonyl Group 557 III General Reactions of Carbonyl Compounds 557 IV Summary 562 Exercises 563 Aldehydes and Ketones: Nucleophilic Addition Reactions 564 14.1 Naming Aldehydes and Ketones 565 14.2 Preparing Aldehydes and Ketones 567 14.3 Oxidation of Aldehydes 568 14.4 Nucleophilic Addition Reactions of Aldehydes and Ketones 569 14.5 Nucleophilic Addition of H2O: Hydration 572 14.6 Nucleophilic Addition of Grignard and Hydride Reagents: Alcohol Formation 574 14.7 Nucleophilic Addition of Amines: Imine and Enamine Formation 576 14.8 Nucleophilic Addition of Alcohols: Acetal Formation 580 14.9 Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction 583 14.10 Biological Reductions 587 14.11 Conjugate Nucleophilic Addition to ,-Unsaturated Aldehydes and Ketones 588 14.12 Spectroscopy of Aldehydes and Ketones 593 Summary 596 Summary of Reactions 597 Lagniappe—Enantioselective Synthesis 599 Exercises 600 14 39144_ FM_i-xxiv.indd xii 8/26/09 10:48:50 AM