Chapter 1 Chemical Bonding 1
1.1 Introduction 1
1.2 Atoms,Electrons and Orbitals 1
1.3 Ionic Bonds 3
1.4 Covalent Bonds 4
1.5 Double Bonds and Triple Bonds 5
1.6 Polar Covalent Bonds and Electronegativity 5
1.7 Formal Charge 6
1.8 Structural Formulas of Organic Molecules 6
1.9 Constitutional Isomers 7
1.10 Resonance 7
1.11 The Shapes of Some Simple Molecules 8
1.12 Molecular Dipole Moments 9
1.13 Electron Waves and Chemical Bonds 10
1.14 Bonding in H2:The Valence Bond Model 11
1.15 Bonding in H2:Molecular Orbital Method 12
1.16 Orbital Hybridization and Bonding of Methane 13
1.17 sp3 Hybridization and Bonding of Ethane 14
1.18 sp2 Hybridization and Bonding of Ethylene 14
1.19 sp Hybridization and Bonding of Acetylene 15
1.20 Chapter Summary 16
Review Questions 18
References 20
Chapter 2 Alkanes and Cycloalkanes 21
2.1 Introduction 21
2.2 Structure of Alkanes 22
2.3 Nomenclature of Alkanes 22
2.4 Alkyl Groups 24
2.5 Conformational Isomerization of Alkanes 24
2.6 Physical Properties of Alkanes 27
2.7 Chemical Properties of Alkanes 28
2.8 Cycloalkanes 30
2.9 Chapter Summary 35
Review Questions 36
References 38
Chapter 3 Alkenes and Alkynes 39
3.1 Introduction of Alkenes 39
3.2 Structure of Alkenes 40
3.3 Nomenclature of Alkenes 40
3.4 Physical Properties of Alkenes 42
3.5 Chemical Properties of Alkenes 42
3.6 Dienes 50
3.7 Introduction of Alkynes 54
3.8 Structure of Alkynes 54
3.9 Nomenclature of Alkynes 54
3.10 Physical Properties of Alkynes 55
3.11 Chemical Properties of Alkynes 55
3.12 Chapter Summary 60
Review Questions 61
References 63
Chapter 4 Aromatic Compounds 64
4.1 Introduction 64
4.2 Benzene 65
4.3 Nomenclature of Benzene Derivatives 66
4.4 Physical Properties of Aromatic Hydrocarbon 69
4.5 Chemistry of Benzene Derivatives 70
4.6 Fused-Ring Aronatic Hydrocarbons 80
4.7 Aromaticity and the Hückel Rule 82
4.8 Chapter Summary 84
Review Questions 85
References 88
Chapter 5 Stereochemistry 89
5.1 Introduction 89
5.2 Symmetry Elements 90
5.3 Chiral Carbons 91
5.4 Optical Activity 94
5.5 Configuration of Enantiomers 95
5.6 Isomers with More than One Asymmetric Centers 96
5.7 Chapter Summary 98
Review Questions 98
References 101
Chapter 6 Alkyl Halides 102
6.1 Introduction 102
6.2 Classification 103
6.3 Nomenclature 103
6.4 Reactions of Alkyl Halides 104
6.5 Chapter Summary 111
Review Questions 112
References 115
Chapter 7 Alcohols and Phenols 116
7.1 Introduction 116
7.2 Alcohols 117
7.3 Phenols 124
7.4 Chapter Summary 127
Review Questions 127
References 129
Chapter 8 Ethers,Epoxides,Thiols and Sulfides 130
8.1 Introduction 130
8.2 Nomenclature of Ethers 131
8.3 Structures and Physical Properties of Ethers 132
8.4 Preparations of Ethers 132
8.5 Reactions of Ethers 134
8.6 Crown Ethers 137
8.7 Epoxides 138
8.8 Thiols and Sulfides 142
8.9 Chapter Summary 144
Review Questions 147
References 152
Chapter 9 Aldehydes and Ketones 153
9.1 Introduction 153
9.2 Classification and Nomenclature of Aldehydes and Ketones 154
9.3 Structures of Aldehydes and Ketones 155
9.4 Physical Properties of Aldehydes and Ketones 156
9.5 Chemical Properties of Aldehydes and Ketones 156
9.6 Quinones 174
9.7 Chapter Summary 177
Review Questions 178
References 183
Chapter 10 Carboxylic Acids and Substituted Carboxylic Acids 184
10.1 Introduction 184
10.2 Structure of Carboxylic Acids 184
10.3 Classification of Carboxylic Acids 185
10.4 Nomenclature of Carboxylic Acids 185
10.5 Chemical Properties and Reactions of Carboxylic Acids 186
10.6 Substituted Carboxylic Acids 192
10.7 Chapter Summary 194
Review Questions 195
References 198
Chapter 11 Carboxylic Acid Derivatives 199
11.1 Introduction 199
11.2 Acyl Halides 200
11.3 Acid Anhydrides 202
11.4 Esters 203
11.5 Amides 206
11.6 Urea 207
11.7 The Claisen Condensation 208
11.8 Chapter Summary 209
Review Questions 209
References 212
Chapter 12 Amines 213
12.1 Introduction 213
12.2 Nomenclature of Amines 214
12.3 Physical Properties of Amines 215
12.4 Synthesis of Amines 215
12.5 Reactions of Amines 218
12.6 Reactions of Arenediazonium Salts 221
12.7 Diazonium Coupling Reaction 223
12.8 Chapter Summary 223
Review Questions 223
References 226
Chapter 13 Aromatic Heterocycles 227
13.1 Introduction 227
13.2 Classification and Nomenclature of Heterocycles 228
13.3 Five-Membered Heterocycles 229
13.4 Chapter Summary 240
Review Questions 240
References 242
Chapter 14 Carbohydrates 243
14.1 Introduction 243
14.2 Conformations of Sugars 246
14.3 Polyfunctional Chemistry of Sugars 251
14.4 Complex Sugars in Nature 253
14.5 Chapter Summary 256
Review Questions 257
References 258
Chapter 15 Lipids 259
15.1 Introduction 259
15.2 Triglycerides 259
15.3 Phospholipids 262
15.4 Steroids 263
15.5 Chapter Summary 264
Review Questions 265
References 268
Index 269