有机化学（英文改编版）

CONTENTS
Chapter 1 Introduction to Organic Chemistry 1
1.1 Organic Chemistry and Organic Compounds 1
1.2 Bonding 3
1.3 Electronegativity， Bond Polarity and Polarity of Molecules 12
1.4 Acids and Bases 14
1.5 Functional Groups 20
1.6 Intermolecular Forces 25
1.7 Physical Properties 28
1.8 Understanding Organic Reactions 33
Chapter 2 Alkanes and Radical Substitution Reaction 45
2.1 Introduction 45
2.2 Nomenclature of Alkanes* 47
2.3 Physical Properties of Alkanes 53
2.4 Conformations of Acyclic Alkanes 54
2.5 Conformations of Cycloalkanes 59
2.6 Oxidation of Alkanes 64
2.7 Radical Substitution of Alkanes 66
Chapter 3 Stereochemistry 76
3.1 Introduction 76
3.2 The Two Major Classes of Isomers 76
3.3 Looking Glass ChemistryChiral and Achiral Molecules 77
3.4 Compounds with One Stereogenic Centers 79
3.5 Compounds with Two or More Stereogenic Centers 87
3.6 Isomers： A Summary 91
3.7 Physical Properties of Stereoisomers 91
3.8 Focus on Chiral Drugs: Bioactivities of Enantiomers 94
Chapter 4 Alkenes—Electrophilic Addition 100
4.1 Introduction 100
4.2 Electrophilic Additions of Alkenes 106
4.3 Reduction of Alkenes 114
4.4 Oxidations of Alkenes 115
4.5 DienesConjugated Addition 118
Chapter 5 Alkynes 131
5.1 Introduction 131
5.2 Reactions of Alkynes 134
Chapter 6 Alkyl Halides—Nucleophilic Substitution and Elimination 147
6.1 Introduction 147
6.2 Nucleophilic Substitution of Alkyl Halides 149
6.3 Elimination of Alkyl Halides 159
6.4 Organometallic Reagents 170
_ Vi _ TEXTBOOK OF ORGANIC CHEMISTRY
6.5 Focus on Environment: The Ozone Layer and CFCs 171
Chapter 7 Alcohols， Ethers， Epoxides， Thiols and Sulfides 176
7.1 Introduction 176
7.2 Reactions of Alcohols 181
7.3 Reaction of Ethers with Strong Acid 191
7.4 Epoxides 192
7.5 Thiols and Sulfides 196
7.6 Focus on Health 197
Chapter 8 Spectroscopy of Organic Compounds 203
8.1 UV-Visible Spectroscopy 203
8.2 Infrared Spectroscopy 207
8.3 Mass Spectrometry 213
8.4 Nuclear Magnetic Resonance Spectroscopy 221
Chapter 9 Benzene and Aromatic Compounds—Electrophilic Substitution 246
9.1 Introduction 246
9.2 Hiickel，s Rule 249
9.3 Reactions of Aromatic Compounds 254
9.4 Phenols and Related Compounds 271
9.5 Focus on Medicine 274
Chapter 10 Aldehydes and Ketones—Nucleophilic Addition 281
10.1 Introduction 281
10.2 Reactions of Aldehydes and Ketones 286
10.3 a， y9-Unsaturated Carbonyl Compounds 318
Chapter 11 Carboxylic Acids and Substituted Carboxyllc Acids 327
11.1 Introduction 327
11.2 Acidity of Carboxylic Acids 333
11.3 Reactions of Carboxylic Acids 339
11.4 a-Substituted Carboxylic Acids 342
Chapter 12 Carboxylic Acid Derivatives—Nucleophilic Acyl Substitution 349
12.1 Introduction 349
12.2 Nucleophilic Acyl Substitution 357
12.3 Reduction of Carboxylic Acid Derivatives 367
12.4 Nitriles 370
12.5 Carbonyl Condensation Reactions 372
Chapter 13 Amines 386
13.1 Introduction 386
13.2 Reactions of Amines 393
13.3 Reactions of Aryl Diazonium Salts 403
Chapter 14 Amino Acids and Proteins 413
14.1 Amino Acids 413
14.2 Peptides 418
14.3 Proteins 428
Chapter 15 Aromatic Heterocycles 438
15.1 Nomenclature and Classification 438
15.2 Pyrrole， Furan， and Thiophene 438
15.3 Pyridine 441
15.4 Some Important Aromatic Heterocycles in Nature 444
15.5 Alkaloids with Aromatic Heterocycle 447
15.6 An Introduction of Nucleic Acids 450
Chapter 16 Carbohydrates 460
16.1 Introduction 460
16.2 Monosaccharides 461
16.3 Disaccharides 477
16.4 Polysaccharides 479
16.5 Other Important Sugars and Their Derivatives 480
Chapter 17 Lipids 486
17.1 Introduction 486
17.2 Waxes， Fats and Oils 487
17.3 Phospholipids 489
17.4 Terpenes 491
17.5 Steroids 492
17.6 Fat-Soluble Vitamins 494
17.7 Eicosanoids 495