Contents 8 -Haloalkanes,Halogenation,and Radical Reactions 305 8.1 Structure 306 8.2 Nomenclature 306 8.3 Physical Properties of Haloalkanes 307 8.4 Preparation of Haloalkanes by Halogenation of Alkanes 311 8.5 Mechanism of Halogenation of Alkanes 315 CHEMICAL CONNECTIONS Freons 318 8.6 Allylic Halogenation 322 8.7 Radical Autoxidation 327 MCAT PRACTICE:PASSAGE AND QUESTIONS Antioxidants 328 8.8 Radical Addition of HBr to Alkenes 330 Summary 333.Problems 335 9Nucleophilic Substitution and B-Elimination 341 9.1 Nucleophilic Substitution in Haloalkanes 343 .2 Mechanisms of Nucleophilic Aliphatic Substitution 344 9.3 Experimental Evidence for S.,1 and S.2 Mechanisms 348 9.4 Analysis of Several Nucleophilic Substitution Reactions 364 9.5 B-Elimination 366 9.6 Mechanisms of B-Elimination 368 9.7 Experimental Evidence for E1 and E2 Mechanisms 370 9.8 Substitution Versus Elimination 376 9.9 Analysis of Several Competitions Between Substitutions and Eliminations 380 MCAT PRACTICE:PASSAGE AND QUESTIONS Solvents and Solvation 383 9.10 Neighboring Group Participation 383 CONNECTIONS TO BIOLOGICAL CHEMISTRY Mustard Gases and the Treatment of Neoplastic Diseases 386 Summary 387 Problems 391 10 Alcohols 401 10.1 Structure and Nomenclature of Alcohols 402 10.2 Physical Properties of Alcohols 404 CONNECTIONS TO BIOLOGICAL CHEMISTRY The Importance of Hydrogen Bonding in Drug-Receptor Interactions 406 10.3 Acidity and Basicity of Alcohols 408 10.4 Reaction of Alcohols with Active Metals 409 Unless otherwise noted all art on this pageCengage Learning 2013 Unless otherwise noted all art on this page © Cengage Learning 2013 Contents x 8 Haloalkanes, Halogenation, and Radical Reactions 305 8.1 Structure 306 8.2 Nomenclature 306 8.3 Physical Properties of Haloalkanes 307 8.4 Preparation of Haloalkanes by Halogenation of Alkanes 311 8.5 Mechanism of Halogenation of Alkanes 315 CHEMICAL ConnECTIonS Freons 318 8.6 Allylic Halogenation 322 8.7 Radical Autoxidation 327 MCAT PrACTICE: PASSAgE And QuESTIonS Antioxidants 328 8.8 Radical Addition of HBr to Alkenes 330 Summary  333 • Problems  335 9 Nucleophilic Substitution and b-Elimination 341 9.1 Nucleophilic Substitution in Haloalkanes 343 9.2 Mechanisms of Nucleophilic Aliphatic Substitution 344 9.3 Experimental Evidence for SN1 and SN2 Mechanisms 348 9.4 Analysis of Several Nucleophilic Substitution Reactions 364 9.5 b-Elimination 366 9.6 Mechanisms of b-Elimination 368 9.7 Experimental Evidence for E1 and E2 Mechanisms 370 9.8 Substitution Versus Elimination 376 9.9 Analysis of Several Competitions Between Substitutions and Eliminations 380 MCAT PrACTICE: PASSAgE And QuESTIonS Solvents and Solvation 383 9.10 Neighboring Group Participation 383 ConnECTIonS To BIoLogICAL CHEMISTry Mustard Gases and the Treatment of Neoplastic Diseases 386 Summary  387 • Problems  391 10 Alcohols 401 10.1 Structure and Nomenclature of Alcohols 402 10.2 Physical Properties of Alcohols 404 ConnECTIonS To BIoLogICAL CHEMISTry The Importance of Hydrogen Bonding in Drug-Receptor Interactions 406 10.3 Acidity and Basicity of Alcohols 408 10.4 Reaction of Alcohols with Active Metals 409 Copyright 2013 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