Contents Problem-Solving Strategy:Organic Synthesis 372 Summary:Reactions of Alkenes 374 Chapter 8 Glossary 379 Study Problems 382 O ALKYNES 388 9-1 Introduction 388 9-2 Nomenclature of Alkynes 389 9-3 Physical Pro erties of Alkynes 390 9.4 Commercial Importance of Alkynes 390 9-5 Electronic Structure of Alkynes 392 9-6 Acidity of Alkynes:Formation of Acetylide Ions 393 9-7 Synthesis of Alkynes from Acetylides 395 9-8 Synthesis of Alkynes by Elimination Reactions 399 Summary:Syntheses of Alkynes Addition F Summary:Reactions of Alkynes 414 Chapter 9 Glossary 417 Study Problems 418 10 STRUCTURE AND SYNTHESIS OF ALCOHOLS 421 Introduction 42 Structure and Cl sification of Alcohol 2 ture of Alco Physical ies of Al hals Acidity of Alcoh 43 10-7Sy the is of Alcohols:In and Review 434 Summary:Previous Alcohol sv 10-8 Organometallic Reagents for Alcohol Synthesis 436 10-9 Addition of Organometallic Reagents to Carbonyl Compounds 439 Key Mechanism:Grignard Reactions 439 Summary:Grignard Reactions 446 10-10 Side Reactions of Organometallic Reagents:Reduction of Alkyl Halides 447 10-11 Reduction of the Carbonyl Group:Synthesis of 1 and 2 Alcohols 449 Summary:Reactions of LiAlH,and NaBH 452 10-12 Thiols (Mercaptans)455 Chapter 10 Glossary 457 Study Problems 459 11 REACTIONS OF ALCOHOLS 464 11-1 Oxidation State es of Alcohols and Related Functional Groups 46 idizing Alcohols 469 x Contents Problem-Solving Strategy: Organic Synthesis 372 Summary: Reactions of Alkenes 374 Chapter 8 Glossary 379 Study Problems 382 9 ALKYN ES 388 9-1 Introduction 388 9-2 Nomenclature of Alkynes 389 9-3 Physical Properties of Alkynes 390 9-4 Commercial Importance of Alkynes 390 9-5 Electronic Structure of Alkynes 392 9-6 Acidity of Alkynes; Formation of Acetylide Ions 393 9-7 Synthesis of Alkynes from Acetylides 395 9-8 Synthesis of Alkynes by Elimination Reactions 399 Summary: Syntheses of Alkynes 400 9-9 Addition Reactions of Alkynes 40 l 9-10 Oxidation of Alkynes 411 Problem-Solving Strategy: Multistep Synthesis 413 Summary: Reactions of Alkynes 414 Chapter 9 Glossary 417 Study Problems 418 1 Q STRUCTURE AND SYNTHESIS OF ALCOHOLS 421 10-1 Introduction 421 10-2 Structure and Classification of Alcohols 421 10-3 Nomenclature of Alcohols and Phenols 423 10-4 Physical Properties of Alcohols 427 10-5 Commercially Important Alcohols 429 10-6 Acidity of Alcohols and Phenols 431 10-7 Synthesis of Alcohols: Introduction and Review 434 Summary: Previous Alcohol Syntheses 434 10-8 Organometallic Reagents for Alcohol Synthesis 436 10-9 Addition of Organometallic Reagents to Carbonyl Compounds 439 Key Mechanism: Grignard Reactions 439 Summary: Grignard Reactions 446 10-10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides 447 10-11 Reduction of the Carbonyl Group: Synthesis of 1 o and 2° Alcohols 449 Summary: Reactions of LiAlH4 and NaBH4 452 Summary: Alcohol Syntheses by Nucleophilic Additions to Carbonyl Groups 453 10-12 Thiols (Mercaptans) 455 Chapter 10 Glossary 457 Study Problems 459 11 REACTIONS OF ALCOHOLS 464 11-1 Oxidation States of Alcohols and Related Functional Groups 464 11-2 Oxidation of Alcohols 466 11-3 Additional Methods for Oxidizing Alcohols 469