Contents in Brief Prologue 1 1 Structure and Bonding 6 2 Acids and Bases 54 Introduction to Organic Molecules and Functional Groups 81 Alkanes 113 5 Stereochemistry 159 6 Understanding organic Reactions 196 1 Alkyl Halides and Nucleophilic Substitution 228 8 Alkyl Halides and Elimination Reactions 278 9 Alcohols,Ethers,and Epoxides 312 10 Alkenes 358 426 Mass Spectrometry and Infrared Spectroscopy 463 14 Nuclear Magnetic Resonance Spectroscopy 494 15 Radical Reactions 538 1617 Conjugation,Resonance,and Dienes 571 Benzene and Aromatic Compounds 607 18 Electrophilic Aromatic Substitution 641 19 Carboxylic Acids and the Acidity of the O-H Bond 688 20 batcenncateelc I Ch mistry;Organometallic Reagents Aldehydes and Keto -Nucleophilic Addition 774 22 Carboxylic Acids and Their Derivatives-Nucleophilic Acyl Substitution 82 2 Substitution Reactions of Carbonyl Compounds at the a Carbon 880 24 Carbonyl Condensation Reactions 916 Amines 949 Carbon-Carbon Bond-Forming Reactions in Organic Synthesis 1002 Carbohydrates 1027 28 Amino Acids and Proteins 1074 29 Lipids 1119 30 Synthetic Polymers 1148 Appendices A-1 Glossary G-1 Credits C-1 Index 1-1v Contents in Brief Prologue 1 1 Structure and Bonding 6 2 Acids and Bases 54 3 Introduction to Organic Molecules and Functional Groups 81 4 Alkanes 113 5 Stereochemistry 159 6 Understanding Organic Reactions 196 7 Alkyl Halides and Nucleophilic Substitution 228 8 Alkyl Halides and Elimination Reactions 278 9 Alcohols, Ethers, and Epoxides 312 10 Alkenes 358 11 Alkynes 399 12 Oxidation and Reduction 426 13 Mass Spectrometry and Infrared Spectroscopy 463 14 Nuclear Magnetic Resonance Spectroscopy 494 15 Radical Reactions 538 16 Conjugation, Resonance, and Dienes 571 17 Benzene and Aromatic Compounds 607 18 Electrophilic Aromatic Substitution 641 19 Carboxylic Acids and the Acidity of the O–H Bond 688 20 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction 721 21 Aldehydes and Ketones—Nucleophilic Addition 774 22 Carboxylic Acids and Their Derivatives—Nucleophilic Acyl Substitution 825 23 Substitution Reactions of Carbonyl Compounds at the α Carbon 880 24 Carbonyl Condensation Reactions 916 25 Amines 949 26 Carbon–Carbon Bond-Forming Reactions in Organic Synthesis 1002 27 Carbohydrates 1027 28 Amino Acids and Proteins 1074 29 Lipids 1119 30 Synthetic Polymers 1148 Appendices A-1 Glossary G-1 Credits C-1 Index I-1 smi75625_fm_00i-xxxiv.indd v 11/17/09 11:21:09 AM