i DETAILED CONTENTS 13.6 Protection of Alcohols 13-7 Preparation and Reactions of Thiols 13-8 Ethers and Sulfides 64 13-9 Preparing Ethers 4 13-10 Reactions of Ethers 4 13-11 Crown Ethers and lonophores 472 13.12 Preparation and Reactions of Sulfides 47 13-13 Spectroscopy of Alcohols,Phenols,and Ethers 75 SOMETHING EXTRA Ethanol:Chemical,Drug,Poison 78 A Preview of Carbonyl Chemistry 483 Kinds of Carbonyl Compounds Nature of the Carbonyl Group General Reactions of Carbonyl Compounds Summary 491 4 Aldehydes and Ketones: Nucleophilic Addition Reactions 492 14-1 Naming Aldehydes and Ketones 9 14-2 Preparing Aldehydes and Ketones 14-3 Oxidation of Aldehydes 14.4 Nucleophilic Addition Reactions of Aldehydes and Ketones 497 14-5 Nucleophilic Addition of H2O:Hydration 501 14-6 Nucleophilic Addition of Hydride and Grignard Reagents:Alcohol Formation 14-7 Nucleophilic Addition of Amines:Imine and Enamine Formation 505 14-8 Nucleophilic Addition of Alcohols:Acetal Formation 509 14-9 Nucleophilic Addition of Phosphorus Ylides:The Wittig Reaction 3 14-10 Biological Reductions 14-11 Conjugate Nucleophilic Addition to a,B-Unsaturated Aldehydes and Ketones 518 14.12 Spectroscopy of Aldehydes and Ketones 522 SOMETHING EXTRA Enantioselective Synthesis 526 xii DetaileD Contents 13-6 protection of alcohols 460 13-7 preparation and Reactions of thiols 463 13-8 Ethers and sulfides 464 13-9 preparing Ethers 466 13-10 Reactions of Ethers 467 13-11 crown Ethers and ionophores 472 13-12 preparation and Reactions of sulfides 474 13-13 spectroscopy of alcohols, phenols, and Ethers 475 soMetHinG eXtra Ethanol: chemical, Drug, poison 478 a Preview of Carbonyl Chemistry | 483 i Kinds of carbonyl compounds 483 ii nature of the carbonyl group 485 iii general Reactions of carbonyl compounds 485 iV summary 491 14 aldehydes and Ketones: nucleophilic addition reactions | 492 14-1 naming aldehydes and Ketones 493 14-2 preparing aldehydes and Ketones 495 14-3 oxidation of aldehydes 497 14-4 nucleophilic addition Reactions of aldehydes and Ketones 497 14-5 nucleophilic addition of h2o: hydration 501 14-6 nucleophilic addition of hydride and grignard Reagents: alcohol Formation 503 14-7 nucleophilic addition of amines: imine and Enamine Formation 505 14-8 nucleophilic addition of alcohols: acetal Formation 509 14-9 nucleophilic addition of phosphorus Ylides: the wittig Reaction 513 14-10 Biological Reductions 516 14-11 conjugate nucleophilic addition to a,b-Unsaturated aldehydes and Ketones 518 14-12 spectroscopy of aldehydes and Ketones 522 soMetHinG eXtra Enantioselective synthesis 526 42912_00_FM_i-xxiv.indd 12 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