Contents 10.9 Hydrohalogenation-Electrophilic Addition of HX 371 10.10 Markovnikov's Rule 374 10.11 Stereochemistry of Electrophilic Addition of HX 376 10.12 Hydration-Electrophilic Addition of Water 378 10.13 Halogenation-Addition of Halogen 379 10.14 Stere ochemistry of Halogenation 381 10.15 Halohydrin Fo ation 383 385 Keeping Track of Rec 39 9 Key Concepts 393 Problems 394 11 Alkynes 399 11.1 Introduction 400 11.2 Nomenclature 401 11.3 402 114 Interesti e5402 11.5 4 n to Alkyne Rea ions 11.8 Addition of Halogen 11.9 Addition of Water 11.10 Hydroboration-Oxidation 412 11.11 Reaction of Acetylide Anions 414 11.12 Synthesis 417 Key Concepts 419 Problems 421 12 Oxidation and Reduction 426 educing Ag 428 428 Application:Hydrogenation of Oils 432 12.5 Reduction of Alkynes 434 12.6 The Reduction of Polar C-X o Bonds 437 12.7 Oxidizing Agents 438 12.8 Epoxidation 439 12.9 Dihydroxylation 442 12.10 Oxidative Cleavage of Alkenes 444 12.11 Oxidative Cleavage of Alkynes 446 12.12 Oxidation of Alcc nols 447 12.13 Greer Ch y t on:Th Oxidat of Ethanol 451 451 Key Concepts 454 Problems 457 x Contents 10.9 Hydrohalogenation—Electrophilic Addition of HX 371 10.10 Markovnikov’s Rule 374 10.11 Stereochemistry of Electrophilic Addition of HX 376 10.12 Hydration—Electrophilic Addition of Water 378 10.13 Halogenation—Addition of Halogen 379 10.14 Stereochemistry of Halogenation 381 10.15 Halohydrin Formation 383 10.16 Hydroboration–Oxidation 385 10.17 Keeping Track of Reactions 390 10.18 Alkenes in Organic Synthesis 391 Key Concepts 393 Problems 394 11 Alkynes 399 11.1 Introduction 400 11.2 Nomenclature 401 11.3 Physical Properties 402 11.4 Interesting Alkynes 402 11.5 Preparation of Alkynes 404 11.6 Introduction to Alkyne Reactions 405 11.7 Addition of Hydrogen Halides 406 11.8 Addition of Halogen 409 11.9 Addition of Water 409 11.10 Hydroboration–Oxidation 412 11.11 Reaction of Acetylide Anions 414 11.12 Synthesis 417 Key Concepts 419 Problems 421 12 Oxidation and Reduction 426 12.1 Introduction 427 12.2 Reducing Agents 428 12.3 Reduction of Alkenes 428 12.4 Application: Hydrogenation of Oils 432 12.5 Reduction of Alkynes 434 12.6 The Reduction of Polar C–X σ Bonds 437 12.7 Oxidizing Agents 438 12.8 Epoxidation 439 12.9 Dihydroxylation 442 12.10 Oxidative Cleavage of Alkenes 444 12.11 Oxidative Cleavage of Alkynes 446 12.12 Oxidation of Alcohols 447 12.13 Green Chemistry 450 12.14 Application: The Oxidation of Ethanol 451 12.15 Sharpless Epoxidation 451 Key Concepts 454 Problems 457 smi75625_fm_00i-xxxiv.indd x 11/17/09 11:21:23 AM