本書包括有機化學的烷烴、烯烴、炔烴和芳香烴等烴類；包括含氧化化物的醇、酚、醚、醛、酮、羧酸和羧酸的衍生物；包括含氮化合物的胺類化合物和酰胺類化合物；用獨立章節(jié)介紹有機化合物的同分異構體現(xiàn)象，尤其是光學異構現(xiàn)象；最后介紹了四類與生物體組成密切相關的四大類化合物糖類、蛋白質、脂類和核酸。

Preface

前 言

Welcome to organic chemistry course.

Earlier, we have learned general chemistry. Chemistry is the study of the nature,

properties, and composition of matter, and how these undergo changes. Organic chemistry,

in short, is the study of organic compounds. Some organic compounds have been known

since ancient antiquity. Prehistoric peoples were familiar with sugar, with the fermentation

of the grape and the production of wine, and with the souring of wine under the agency of

acetobacter to produce vinegar. Vegetable oils and animal fats, and the process of making soap

from these substances, have been known for centuries. Since all organic compounds known

at the beginning of the 19th century had been isolated as products of the life process, namely,

all organic compounds were derived from the products of the life process, the belief was

current for a time that organic compound could arise only through operation of a “vital force”

inherent in living cells. Organic compound, the name its self, implies organism. However,

repeated demonstration that compounds identical in all respects with those obtained from

plants and animals could be prepared from mineral materials. Now, most natural products

known have been prepared synthetically, and pure synthetic organic compounds exceed by

far those found in nature. Organic chemicals are put to many varied uses. They are worn

as clothes, eaten as foods, and used as fuels. They include “wonder” drugs, vitamins, and

hormones as well as deadly poisons.

The study of organic compounds is important to anyone who endeavors to understand

the complex activities of living systems and the material world. The vast majority of living

materials are organic compounds such as saccharide, lipid, protein and nucleic acid and so

on. The metabolic process in humans is a series of organic chemical reactions. To understand

clearly these reactions in living organisms at the molecular level, the knowledge of organic

chemistry is essential. Moreover, organic chemistry is also the foundation of biochemistry,

pharmacology, and other subjects related to medicine.

In the text, after the introduction of various molecular framework species (alkanes,

alkenes, arenes), the aliphatic and aromatic compounds are treated together even though their

differences in chemical properties.

The study of organic chemistry by means of the various functional groups continues to

be the simplest, most natural, and most effective way of easing the burdens of the learning

process. Therefore, the text is organized according to functional groups. Organic chemistry

uses functional groups as the framework within which chemical reactions are discussed. Thus,

the emphasis is placed on the reactions that different functional groups undergo, not on the

reactions that prepare them. Moreover, similar reactions are grouped together so that parallels

can be emphasized. Exercises in the text appear both within and at the end of chapters. Those

within the chapters are intended to test comprehension of specific points made in that section

of the text. Exercises at the ends of chapters are more comprehensive and include both drill

and thought questions.

With the joint efforts of some organic chemistry teachers who have taught international

students for many years, the first edition of organic chemistry textbook finally comes into use.

It follows closely the organic chemistry syllabus of clinical medical education for international

students. This textbook has been absorbed feedback from teachers and students actually

teaching and learning organic chemistry. Today’s students rely more heavily on visual

imagery to learn than ever before. We have therefore written the text that uses less written

narrative and more diagrams, equations, tables, and examples to introduce and reinforce the

major concepts and themes of organic chemistry. The text is arranged into twelve chapters

that cover introduction of organic chemistry (chapter 1), hydrocarbons (chapter 2-3), organic

compounds containing oxygen, sulfur and nitrogen (chapter 4-7), optical isomerism (chapter

8), and important life substances ——carbohydrates, lipids, proteins and nucleic acids (chapter

9-12).

Although the book has been carefully modified many times, it is still hard to avoid

mistakes and deficiencies. I earnestly hope broad teachers and students put forward valuable

opinion. Finally, I would like to express my thanks to all cooperators to pay hard work,

especially my colleagues, professor Sun Yanhua and professor Shen Wanqiu, for their

contributions and supports. I would also like to thank the editor staff of Tsinghua university

publishing house for publishing the book's efforts.

Lü Wei

July 15, 2021

教授，中國農(nóng)業(yè)大學應用化學有機合成碩士研究生，2003年天津醫(yī)科大學任教，即開始留學生有機化學教學工作至今，期間，2017年在加拿大McMaster University 做訪問學者，現(xiàn)為校內(nèi)留學生有機化學教材主編。

Contents

目.錄

Chapter 1　Introduction ………………………………1

1.1　Organic Compounds ...........................................1

1.2　Features of Organic Compounds........................2

1.3　The Covalent Bond...............................................2

1.4　Structural Representations of Organic

　Compounds............................................................5

1.5　Functional Groups and Classification of

　Organic Compounds.............................................7

1.6　Isomerism...............................................................8

1.7　Significance of Studying Organic Chemistry for

　Medical Students...................................................9

Chapter 2　Saturated Hydrocarbons: Alkanes and Cycloalkanes……………………11

2.1　Classification of Hydrocarbons.........................11

2.2　Alkanes.................................................................12

2.3　Cycloalkanes .......................................................21

Chapter 3　Unsaturated Hydrocarbons: Alkenes, Alkynes and Aromatics……26

3.1　Alkenes.................................................................26

3.2　Alkynes.................................................................32

3.3　Aromatic Hydrocarbons....................................34

Chapter 4　Alcohols, Phenols, and Ethers……41

4.1　Alcohols................................................................41

4.2　Phenols..................................................................45

4.3　Ethers....................................................................46

4.4　Thioalcohols and Disulfides..............................48

Chapter 5　Aldehydes and Ketones……………52

5.1　Structure of Aldehydes and Ketones...............52

5.2　Nomenclature of Aldehydes and Ketones ..........52

5.3　Physical Properties of Aldehydes and Ketones.............54

5.4　Preparation of Aldehydes and Ketones ..........54

5.5　Chemical Properties of Aldehydes

　 and Ketones.........................................................55

Chapter 6　Carboxylic Acids and Acid Derivatives………………………………65

6.1　Introduction to Acids and Acid Derivatives...65

6.2　Structure and Physical Properties of Carboxylic

　 Acids.....................................................................67

6.3　Naming the Carboxylic Acids...........................69

6.4　Reactions of Carboxylic Acids...........................70

6.5　Reactions which yield carboxylic acids...........74

6.6　Nomenclature of Acid Derivatives...................74

6.7　Physical Properties of Carboxylic Acid

　 Derivatives...........................................................77

6.8　Chemical Properties of Carboxylic Acid

　 Derivatives...........................................................78

Chapter 7　Amines……………………………………87

7.1　Classification and Nomenclature of Amines..87

7.2.Structure of Amines............................................88

7.3　Physical Properties of Amines..........................89

7.4　Chemical Properties of Amines........................89

7.5.Aromatic Diazonium Salts.................................92

7.6.Alkaloids..............................................................92

Chapter 8　Optical Isomerism……………………95

8.1.Optical Activity...................................................95

8.2.Molecular Chirality.............................................97

8.3　Nomenclature of Chiral Carbon Atoms...........98

8.4.Fischer Projections............................................100

8.5　Assigning R or S Configuration to

　Fischer Projections.............................................101

8.6　Compounds Have Two or More

　Chiral Centers....................................................102

8.7　Chirality in the Biological World....................103

Chapter 9　Carbohydrates…………………………108

9.1　Structure and Names of Monosaccharides....108

9.2.Disaccharides.....................................................117

9.3.Polysaccharides.................................................119

Chapter 10　Lipids……………………………………123

10.1　Triacylglycerol—Fats and Oils......................123

10.2　Chemical properties of triacylglycerol.........124

10.3　Fatty Acids in Triacylglycerols......................124

10.4.Glycerophospholipids....................................126

10.5.Steroids.............................................................127

Chapter 11　Amino Acid and Proteins…………130

11.1.Amino Acids....................................................130

11.2.Structures of Polypeptides.............................134

11.3.Structures of Proteins.....................................136

Chapter 12　Nucleic Acids…………………………142

12.1.Pentose..............................................................142

12.2　Heterocyclic Nitrogenous Bases...................142

12.3.Nucleosides......................................................142

12.4.Nucleotides......................................................143

12.5　Primary Structures of Nucleic Acids............143

12.6　Secondary Structure of DNA.........................144

12.7　Higher orders of DNA Structures.................145

12.8　The Roles of DNA and RNA in Genetic

　.Process...............................................................145

References…………………………………………………146