Carey - Organic Chemistry - toc

Carey - Organic Chemistry - toc

Preface xxv

INTRODUCTION 1

The Origins of Organic Chemistry1 Berzelius, Wöhler, and Vitalism1 The Structural Theory3 Electronic Theories of Structure and Reactivity3 The Influence of Organic Chemistry4 Computers and Organic Chemistry4 Challenges and Opportunities5 Where Did the Carbon Come From?6

CHAPTER 1 CHEMICAL BONDING7

Learning By Modeling27

CHAPTER 2 ALKANES 53

xii CONTENTS

CHAPTER 3 CONFORMATIONS OF ALKANES AND CYCLOALKANES89

Molecular Mechanics Applied to Alkanes and Cycloalkanes96

Enthalpy, Free Energy, and Equilibrium Constant106

CHAPTER 4 ALCOHOLS AND ALKYL HALIDES126

CONTENTS xiii

4.11Potential Energy Diagrams for Multistep Reactions: The SN1 Mechanism 143

4.12Effect of Alcohol Structure on Reaction Rate145

4.13Reaction of Primary Alcohols with Hydrogen Halides: The SN2 Mechanism 146

CHAPTER 5 STRUCTURE AND PREPARATION OF ALKENES: ELIMINATION REACTIONS 167

Ethylene 168

Mechanism 192 5.16Anti Elimination in E2 Reactions: Stereoelectronic Effects194 5.17A Different Mechanism for Alkyl Halide Elimination: The E1 Mechanism 196

CHAPTER 6 REACTIONS OF ALKENES: ADDITION REACTIONS208

Rules, Laws, Theories, and the Scientific Method217

xiv CONTENTS

Ethylene and Propene: The Most Important Industrial Organic Chemicals 248

CHAPTER 7 STEREOCHEMISTRY 259

Chiral Drugs273

Chirality of Disubstituted Cyclohexanes281

CHAPTER 8 NUCLEOPHILIC SUBSTITUTION 302

An Enzyme-Catalyzed Nucleophilic Substitution of an Alkyl Halide314

CONTENTS xv

CHAPTER 9 ALKYNES 339

Natural and “Designed” Enediyne Antibiotics344

CHAPTER 10 CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS365

Diene Polymers383

xvi CONTENTS

CHAPTER 1 ARENES AND AROMATICITY398

Benzene, Dreams, and Creative Thinking401

Carbon Clusters, Fullerenes, and Nanotubes410

CHAPTER 12 REACTIONS OF ARENES: ELECTROPHILIC AROMATIC SUBSTITUTION 443

12.1Representative Electrophilic Aromatic Substitution Reactions of

Substituents 463 12.13Substituent Effects in Electrophilic Aromatic Substitution: Strongly

CONTENTS xvii

CHAPTER 13 SPECTROSCOPY 487

Magnetic Resonance Imaging517

CHAPTER 14 ORGANOMETALLIC COMPOUNDS 546

xviii CONTENTS

An Organometallic Compound That Occurs Naturally: Coenzyme B12568

CHAPTER 15 ALCOHOLS, DIOLS, AND THIOLS579

Economic and Environmental Factors in Organic Synthesis598

CHAPTER 16 ETHERS, EPOXIDES, AND SULFIDES619

Polyether Antibiotics 624

CONTENTS xix

CHAPTER 17 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP 654

Imines in Biological Chemistry675

CHAPTER 18 ENOLS AND ENOLATES701

The Haloform Reaction and the Biosynthesis of Trihalomethanes713

x CONTENTS

CHAPTER 19 CARBOXYLIC ACIDS736

Quantitative Relationships Involving Carboxylic Acids743

Reagents 750 19.12Synthesis of Carboxylic Acids by the Preparation and Hydrolysis of

CHAPTER 20 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION 774

Condensation Polymers: Polyamides and Polyesters809

CONTENTS xxi

CHAPTER 21 ESTER ENOLATES831

CHAPTER 2 AMINES 858

Amines as Natural Products869

CHAPTER 23 ARYL HALIDES917

xi CONTENTS

CHAPTER 24 PHENOLS 939

Agent Orange and Dioxin955

CHAPTER 25 CARBOHYDRATES 972

CONTENTS xi

How Sweet It Is!997

CHAPTER 26 LIPIDS 1015

Good Cholesterol? Bad Cholesterol? What’s the Difference? 1038

CHAPTER 27 AMINO ACIDS, PEPTIDES, AND PROTEINS. NUCLEIC ACIDS1051

Electrophoresis 1060

xxiv CONTENTS

APPENDIX 1PHYSICAL PROPERTIESA-1 APPENDIX 2ANSWERS TO IN-TEXT PROBLEMSA-9

APPENDIX 3LEARNING CHEMISTRY WITH MOLECULAR MODELS: Using SpartanBuild and SpartanView A-64

GLOSSARY G-1 CREDITS C-1 INDEX I-1

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