Contents 1
Preface 6
Organic Chemistry 7
1 Atomic Orbitals, Electronic Configurations 8
2 Covalent Bonding 10
3 Hybridization of Atomic Orbitals 12
4 Covalent Carbon-Carbon Bonding 14
5 Alkanes 16
6 Skeletal Structure, Structural Isomerism 18
7 Basic Rules of Nomenclature 20
8 Drawing Molecular Structures 22
9 Conformation 24
10 Reactive Intermediates 26
11 Basic Types of Organic Reactions 28
12 Energy Turnover of Chemical Reactions 30
13 Radical Substitution 32
14 Alkenes, Skeletal and Configurational Isomers 34
15 Synthesis of Alkenes 36
16 Additions to Alkenes 40
17 Dienes 44
18 Additions and Cycloadditions with 1,3-Dienes 46
19 Alkynes 48
20 Cycloalkanes 52
21 Basic Syntheses of Cycloalkanes and Cycloalkenes 56
22 Reactions of Cycloalkanes and Cycloalkenes 58
23 Benzene, Aromaticity, Aromatic Compounds 60
24 Benzenoid Aromatic Compounds 62
25 Electrophilic Substitution of Benzene 64
26 Electrophilic Second Substitution of Benzenes 66
27 Other Reactions of Benzenoid Aromatics 68
28 Polycyclic Benzenoid Aromatic Compounds 70
29 Non-benzenoid Aromatic Compounds 74
30 Alkyl Halides 76
31 Mechanisms of Nucleophilic Substitution 80
32 Organometal Compounds 82
33 Alcohols 84
34 Diols, Triols 88
35 Reactions of Alcohols 90
36 Dehydration of Alcohols 92
37 Ethers 94
38 Amines 96
39 Reactions of Amines 98
40 Diazo and Azo Compounds 102
41 Carboxylic Acids 106
42 Carboxylic Acid Derivatives 110
43 Substituted Carboxylic Acids 114
44 Absolute Configuration 118
45 Enantiomers without Carbon as Stereogenic Center 122
46 Diastereomers 124
47 Aldehydes 126
48 Ketones 130
49 Carbonyl Reactions 132
50 CH Acidity of Carbonyl Compounds 136
51 1,3-Dicarbonyl Compounds 138
52 Phenols 142
53 Quinones 146
54 Organosulfur Compounds 150
55 Carbonic Acid Derivatives 154
56 Heterocumulenes 158
57 Rearrangements 160
58 Polymers, Polymerization 164
59 Syntheses with Organosilicon Compounds 168
60 Heteroalicycles 170
61 Five-Membered Aromatic Heterocycles 174
62 Six-Membered Aromatic Heterocycles 178
63 Benzo-Fused Five-Membered Heteroaromatics 182
64 Benzo-Fused Six-Membered Heteroaromatics 186
65 Fused Aromatic Heterocycles 190
66 Absorption of Light, Color, Dyes 194
67 Porphyrinoids 198
68 Amino Acids 200
69 Peptides, Proteins 202
70 Alkaloids 206
71 Carbohydrates: Aldoses and Ketoses 208
72 Carbohydrates: Oligo- and Polysaccharides 212
73 Nucleic Acids: DNA and RNA 214
74 Lipids 216
75 Polyketides 218
76 Terpenes 220
77 Steroids 224
78 Selectivity and Specificity of Organic Reactions 226
79 Prochirality, Enantioselectivity 230
80 Planning Organic Syntheses 232
81 Aspects of Molecular Structure 236
82 Mass Spectrometry 238
83 Infrared Spectroscopy 240
84 Nuclear Magnetic Resonance: Proton NMR 242
85 Nuclear Magnetic Resonance: Carbon-13 NMR 246
86 Nuclear Magnetic Resonance: Two-Dimensional NMR 248
Working on Questions 250
Subject Index 295
Periodic Table of the Elements 314
Selected Reference Sources 316
