Contents 8-3 Addition of Hydrogen Halides to Alk 331 m83:f 332 cal Additi 8-4 8-4:Acidc 33 f an Alkene 338 8-5 ercuratio curation of an alkene 340 8-6 Alkox ercuration-Demercuration 342 8-7 Hydroboration of Alke Mechanism 8-6:Hydroboration of an Alkene 345 8-8 Addition of Halogens to Alkenes 349 Mechanism 8-7:Addition of Halogens to Alkenes 350 8-9 Formation of Halohydrins 352 Mechanism 8-8:Formation of Halohydrins 352 8-10 Catalytic Hydrogenation of Alkenes 355 8-11 Addition of Carbenes to Alkenes 358 8-12 poxidation of Alkenes 360 Mechanism 8-9:Epoxidation of Alkenes 360 8-13 tion ene 36 anism 8-14 .10. alyzed O ening of Epoxides 362 ylation of lkenes Ken 36 A I 819 nes 36 efin Me 373 nis 811 n Me a Stratea athes376hess370 Summary:Reactions of Alkenes 378 EssentialTerms 383 Study Problems 386 9 △I KYNES3g2 9.1 Introduction 392 02 nes 393 9.3 294 s395 9.5 Electronic Structure of alkynes 396 9-6 Acidity of Alkynes:Formation of Acetylide lons 397 9.7 Synthesis of Alkynes from Acetylides 399 9-8 Synthesis of Alkynes by Elimination Reactions 403 Summary:Syntheses of Alkynes 404 9-g Addition Reactions of Alkynes 405 Mechanism 9-1:Metal-Ammonia Reduction of an Alkyne 407 Mechanism 9-2:Acid-Catalyzed Keto-Enol Tautomerism 411 Mechanism 9-3:Base-Catalyzed Keto-Enol Tautomerism 413 9-10 Oxidation of Alkynes 414 00 Synthesis 416 Summa y:React ns of Alkynes 418 Study ProblemsContents ix 8-3 Addition of Hydrogen Halides to Alkenes 331 Mechanism 8-2: Ionic Addition of HX to an Alkene 332 Mechanism 8-3: Free-Radical Addition of HBr to Alkenes 334 8-4 Addition of Water: Hydration of Alkenes 337 Mechanism 8-4: Acid-Catalyzed Hydration of an Alkene 338 8-5 Hydration by Oxymercuration–Demercuration 340 Mechanism 8-5: Oxymercuration of an Alkene 340 8-6 Alkoxymercuration–Demercuration 342 8-7 Hydroboration of Alkenes 343 Mechanism 8-6: Hydroboration of an Alkene 345 8-8 Addition of Halogens to Alkenes 349 Mechanism 8-7: Addition of Halogens to Alkenes 350 8-9 Formation of Halohydrins 352 Mechanism 8-8: Formation of Halohydrins 352 8-10 Catalytic Hydrogenation of Alkenes 355 8-11 Addition of Carbenes to Alkenes 358 8-12 Epoxidation of Alkenes 360 Mechanism 8-9: Epoxidation of Alkenes 360 8-13 Epoxidation of Alkenes 361 Mechanism 8-10: Acid-Catalyzed Opening of Epoxides 362 8-14 Syn Dihydroxylation of Alkenes 364 8-15 Oxidative Cleavage of Alkenes 366 8-16 Polymerization of Alkenes 369 8-17 Olefin Metathesis 373 Mechanism 8-11: Olefin Metathesis 376 Problem-Solving Strategy: Organic Synthesis 376 Summary: Reactions of Alkenes 378 Essential Terms 383 Study Problems 386 9 ALKYNES 392 9-1 Introduction 392 9-2 Nomenclature of Alkynes 393 9-3 Physical Properties of Alkynes 394 9-4 Commercial Importance of Alkynes 395 9-5 Electronic Structure of Alkynes 396 9-6 Acidity of Alkynes; Formation of Acetylide Ions 397 9-7 Synthesis of Alkynes from Acetylides 399 9-8 Synthesis of Alkynes by Elimination Reactions 403 Summary: Syntheses of Alkynes 404 9-9 Addition Reactions of Alkynes 405 Mechanism 9-1: Metal–Ammonia Reduction of an Alkyne 407 Mechanism 9-2: Acid-Catalyzed Keto–Enol Tautomerism 411 Mechanism 9-3: Base-Catalyzed Keto–Enol Tautomerism 413 9-10 Oxidation of Alkynes 414 Problem-Solving Strategy: Multistep Synthesis 416 Summary: Reactions of Alkynes 418 Essential Terms 421 Study Problems 422