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
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
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