Brief Contents Preface xxv 1 Introduction and Review 1 2 Structure and Properties of Organic Molecules 42 3 Structure and Stereochemistry of Alkanes 87 4 The Study of Chemical Reactions 132 Stereochemistry 174 6 Alkyl Halides:Nucleophilic Substitution and Elimination 218 7 Structure and Synthesis of Alkenes 285 8 Reactions of Alkenes 328 9 Alkynes 392 10 Structure and Synthesis of Alcohols 425 11 Reactions of alcohols 467 12 Infrared Spectroscopy and Mass Spectrometry 513 13 Nuclear Magnetic Resonance Spectroscopy 563 14 Ethers,Epoxides,andThioethers 625 6 Aromatic Compounds 713 17 Reactions of Aromatic Compounds 756 18 Ketones and Aldehydes 816 Amines 879 20 Carboxylic Acids 939 Carboxylic Acid Derivatives 981 22 23 Carbohydrates and Nucleic Acids 1101 24 Amino Acids,Peptides,and Proteins 1155 Lipids 1201 26 Synthetic Polymers 1222 Appendices 1243 Answers A1 Photo Credits PC1 Index 11 iv Brief Contents Preface xxv 1 Introduction and Review 1 2 Structure and Properties of Organic Molecules 42 3 Structure and Stereochemistry of Alkanes 87 4 The Study of Chemical Reactions 132 5 Stereochemistry 174 6 Alkyl Halides: Nucleophilic Substitution and Elimination 218 7 Structure and Synthesis of Alkenes 285 8 Reactions of Alkenes 328 9 Alkynes 392 10 Structure and Synthesis of Alcohols 425 11 Reactions of Alcohols 467 12 Infrared Spectroscopy and Mass Spectrometry 513 13 Nuclear Magnetic Resonance Spectroscopy 563 14 Ethers, Epoxides, and Thioethers 625 15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy 667 16 Aromatic Compounds 713 17 Reactions of Aromatic Compounds 756 18 Ketones and Aldehydes 816 19 Amines 879 20 Carboxylic Acids 939 21 Carboxylic Acid Derivatives 981 22 Condensations and Alpha Substitutions of Carbonyl Compounds 1045 23 Carbohydrates and Nucleic Acids 1101 24 Amino Acids, Peptides, and Proteins 1155 25 Lipids 1201 26 Synthetic Polymers 1222 Appendices 1243 Answers A1 Photo Credits PC1 Index I1 iv