Organic chemistry: mechanistic patterns 9780176500269, 017650026X
271 25 58MB
English Pages [1279] Year 2017;2019
Table of contents :
COVER......Page 1
BRIEF CONTENTS......Page 7
CONTENTS......Page 9
ABOUT THE AUTHORS......Page 13
FOREWORD......Page 15
PREFACE......Page 16
CHAPTER 1 Carbon and Its Compounds......Page 27
CHAPTER 2 Anatomy of an Organic Molecule......Page 73
CHAPTER 3 Molecules in Motion: Conformations by Rotations......Page 112
CHAPTER 4 Stereochemistry: Three-Dimensional Structure in Molecules......Page 151
CHAPTER 5 Organic Reaction Mechanism: Using Curved Arrows to Analyze Reaction Mechanisms......Page 212
CHAPTER 6 Acids and Bases......Page 261
CHAPTER 7 π Bonds as Electrophiles: Reactions of Carbonyls and Related Functional Groups......Page 298
CHAPTER 8 π Bonds as Nucleophiles: Reactions of Alkenes, Alkynes, Dienes, and Enols......Page 354
CHAPTER 9 Conjugation and Aromaticity......Page 424
CHAPTER 10 Synthesis Using Aromatic Materials: Electrophilic Aromatic Substitution and Directed Ortho Metalation......Page 457
CHAPTER 11 Displacement Reactions on Saturated Carbons: SN1 and SN2 Substitution Reactions......Page 520
CHAPTER 12 Formation of π Bonds by Elimination Processes: Elimination and Oxidation Reactions......Page 566
CHAPTER 13 Structure Determination I: Nuclear Magnetic Resonance Spectroscopy......Page 603
CHAPTER 14 Structure Determination II: Mass Spectrometry and Infrared Spectroscopy......Page 674
CHAPTER 15 π Bond Electrophiles Connected to Leaving Groups: Carboxylic Acid Derivatives......Page 722
CHAPTER 16 π Bonds with Hidden Leaving Groups: Reactions of Acetals and Related Compounds......Page 790
CHAPTER 17 Carbonyl-Based Nucleophiles: Aldol, Claisen, Wittig, and Related Enolate Reactions......Page 836
CHAPTER 18 Selectivity and Reactivity in Enolate Reactions: Control of Stereoselectivity and......Page 925
CHAPTER 19 Radicals: Halogenation, Polymerization, and Reduction Reactions......Page 997
CHAPTER 20 Reactions Controlled by Orbital Interactions: Ring Closures, Cycloadditions, and Rearrangements......Page 1037
Appendix A Answers to Checkpoint Problems......Page 1103
Appendix B Common Errors in Organic Structures and Mechanisms......Page 1239
Appendix C pKa Values of Selected Organic Compounds......Page 1243
Appendix D NMR and IR Spectroscopic Data......Page 1245
Appendix E Periodic Table of the Elements......Page 1247
GLOSSARY......Page 1249
INDEX......Page 1263
COVER......Page 1
BRIEF CONTENTS......Page 7
CONTENTS......Page 9
ABOUT THE AUTHORS......Page 13
FOREWORD......Page 15
PREFACE......Page 16
CHAPTER 1 Carbon and Its Compounds......Page 27
CHAPTER 2 Anatomy of an Organic Molecule......Page 73
CHAPTER 3 Molecules in Motion: Conformations by Rotations......Page 112
CHAPTER 4 Stereochemistry: Three-Dimensional Structure in Molecules......Page 151
CHAPTER 5 Organic Reaction Mechanism: Using Curved Arrows to Analyze Reaction Mechanisms......Page 212
CHAPTER 6 Acids and Bases......Page 261
CHAPTER 7 π Bonds as Electrophiles: Reactions of Carbonyls and Related Functional Groups......Page 298
CHAPTER 8 π Bonds as Nucleophiles: Reactions of Alkenes, Alkynes, Dienes, and Enols......Page 354
CHAPTER 9 Conjugation and Aromaticity......Page 424
CHAPTER 10 Synthesis Using Aromatic Materials: Electrophilic Aromatic Substitution and Directed Ortho Metalation......Page 457
CHAPTER 11 Displacement Reactions on Saturated Carbons: SN1 and SN2 Substitution Reactions......Page 520
CHAPTER 12 Formation of π Bonds by Elimination Processes: Elimination and Oxidation Reactions......Page 566
CHAPTER 13 Structure Determination I: Nuclear Magnetic Resonance Spectroscopy......Page 603
CHAPTER 14 Structure Determination II: Mass Spectrometry and Infrared Spectroscopy......Page 674
CHAPTER 15 π Bond Electrophiles Connected to Leaving Groups: Carboxylic Acid Derivatives......Page 722
CHAPTER 16 π Bonds with Hidden Leaving Groups: Reactions of Acetals and Related Compounds......Page 790
CHAPTER 17 Carbonyl-Based Nucleophiles: Aldol, Claisen, Wittig, and Related Enolate Reactions......Page 836
CHAPTER 18 Selectivity and Reactivity in Enolate Reactions: Control of Stereoselectivity and......Page 925
CHAPTER 19 Radicals: Halogenation, Polymerization, and Reduction Reactions......Page 997
CHAPTER 20 Reactions Controlled by Orbital Interactions: Ring Closures, Cycloadditions, and Rearrangements......Page 1037
Appendix A Answers to Checkpoint Problems......Page 1103
Appendix B Common Errors in Organic Structures and Mechanisms......Page 1239
Appendix C pKa Values of Selected Organic Compounds......Page 1243
Appendix D NMR and IR Spectroscopic Data......Page 1245
Appendix E Periodic Table of the Elements......Page 1247
GLOSSARY......Page 1249
INDEX......Page 1263
