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

Chapter 1 Introduction to Organic Chemistry
1.1 Organic Chemistry and Organic Compounds
1.1.1 What Are Organic Chemistry and Organic Compounds?
Organic chemistry is the chemistry subdiscipline for the scientific study of nomenclature， structure， physical and chemical properties of organic compounds and their applications， which is one branch in the entire field of chemistry， and encompasses many classical subdisciplines including inorganic， physical， and analytical chemistry， and newer fields such as bioinorganic chemistry， bioorganic chemistry， physical biochemistry， polymer chemistry， and materials science.
In general， an organic compound is defined as any compound containing carbon， but some compounds are excepted for historical reasons.
Organic chemistry was singled out as a separate discipline for historical reasons. Originally， it was thought that compounds in living things， termed organic compounds， were fundamentally different from those in nonliving things， called inorganic compounds. Although we have known for more than 150 years that this distinction is artificial， the name organic persists. Today the term refers to the study of the compounds that contain carbon， many of which， incidentally， are found in living organisms. Some compounds that contain the element carbon are not organic compounds. Examples include carbon dioxide (C02)， sodium carbonate (Na2C03)， and sodium bicarbonate (NaHC03).
There are far more organic compounds than any other type. Organic chemicals affect virtually every facet of our lives， and for this reaction， it is important and useful to know something about them.
Clothes， foods， medicines， gasoline， refrigerants， and soaps are composed almost solely of organic compounds. Some， like cotton， wool， or silk are naturally occurring; that is， they can be isolated directly from natural sources. Others， such as nylon and polyester， are synthetic， meaning they are produced by chemists in the laboratory. By studying the principles and concepts of organic chemistry， you can learn more about compounds such as these and how they affect the world around you.
Realize， too， what organic chemistry has done for us. Organic chemistry has made available both comforts and necessities that were previously nonexistent， or reserved for only the wealthy. We have seen an enormous increase in life span， from 47 years in 1900 to over 70 years currently. To a large extent this is due to the isolation and synthesis of new drugs to fight infections and the availability of vaccines for childhood diseases. Chemistry has also given us the tools to control insect populations that spread disease， and there is more food for all because of fertilizers， pesticides， and herbicides. Our lives would be vastly different today without the many products that result from organic chemistry. For examples， oral contraceptives， antibiotics， plastic syringes， and the knitted material used in synthetic heart valves are all organic chemicals used in medicine.
1.1.2 Some Representative Organic Molecules
Perhaps the best way to appreciate the variety of organic molecules is to look at a few. Three simple organic compounds are methane， ethanol and trichlorofluoromethane.
Methane， the simplest of all organic compounds， contains one carbon atom. Methane is the main component of natural gas， and occurs widely in nature. Like other hydrocar-bons-organic compounds that contain only carbon and hydrogen-methane is combustible; that is， it bums in the presence of oxygen. Methane is the product of the anaerobic (without air) decomposition of organic matter by bacteria. The natural gas we use today was formed by the decomposition of organic material millions of years ago.
Ethanol， the alcohol present in beer， wine， and other alcoholic beverages， is formed by the fermentation of sugar， quite possibly the oldest example of organic synthesis. Ethanol can also be made in the lab by a totally different process， but the ethanol produced in the lab is identical to the ethanol produced by fermentation.
Trichlorofluoromethane is a member of a class of molecules called chlorofluorocarbons or CFCs，which contain one or two carbon atoms and several halogens. Trichlorofluoromethane is an unusual organic molecule in that it contains no hydrogen atoms. Because it has a low molecular weight and is easily vaporized， trichlorofluoromethane has been used as an aerosol propellant and refrigerant. It and other CFCs have been implicated methane ethanol trichlorofluoromethane capsaicin DDT.
Capsaicin， one member of a group of compounds called vanilloids， is responsible for the characteristic spiciness of hot peppers. It is the active ingredient in pepper sprays used for personal defense and topical creams used for pain relief.
DDT， dichlorodiphenyltrichloroethane， is a pesticide once called “miraculous” by Winston Churchill because of the many lives it saved by killing disease-carry