1
课程详述
COURSE SPECIFICATION
以下课程信息可能根据实际授课需要或在课程检讨之后产生变动。如对课程有任何疑问，请联
系授课教师。
The course information as follows may be subject to change, either during the session because of unforeseen
circumstances, or following review of the course at the end of the session. Queries about the course should be
directed to the course instructor.
1.
课程名称 Course Title
有机化学 I Organic Chemistry I
2.
授课院系
Originating Department
化学系 Department of Chemistry
3.
课程编号
Course Code
CH203
4.
课程学分 Credit Value
4
5.
课程类别
Course Type
专业基础课 Major Foundational Courses
6.
授课学期
Semester
秋季 Fall
7.
授课语言
Teaching Language
中英双语 English & Chinese
8.
授课教师、所属学系、联系方
式（如属团队授课，请列明其
他授课教师）
Instructor(s), Affiliation&
Contact
（For team teaching, please list
all instructors）
李鹏飞，助理教授，化学系， li.pf@sustech.edu.cn
汪君，助理教授，化学系，wang.j@sustech.edu.cn
何川，副教授，化学系，hec@sustech.edu.cn
徐晨，助理教授，化学系，xuc@sustech.edu.cn
Pengfei Li, Assistant Professor, Department of Chemistry, li.pf@sustech.edu.cn;
Jun Wang, Assistant Professor, Department of Chemistry, wang.j@sustech.edu.cn
Chuan He, Associate Professor, Department of Chemistry, hec@sustech.edu.cn
Chen Xu, Assistant Professor, Department of Chemistry, xuc@sustech.edu.cn
9.
实验员/助教、所属学系、联系
方式
Tutor/TA(s), Contact
穆怀雪，化学系，muhx@mail.sustech.edu.cn
Huaixue Mu, Department of Chemistry, muhx@mail.sustech.edu.cn
10.
选课人数限额(可不填)
Maximum Enrolment
（Optional）
2
授课方式
Delivery Method
讲授
Lectures
习题/辅导/讨论
Tutorials
实验/实习
Lab/Practical
其它(请具体注明)
Other（Please specify）
总学时
Total
11.
学时数
Credit Hours
64
0
0
0
64
12.
先修课程、其它学习要求
Pre-requisites or Other
Academic Requirements
化学原理 A（CH101A）
13.
后续课程、其它学习规划
Courses for which this course
is a pre-requisite
有机化学 II（CH206）
14.
其它要求修读本课程的学系
Cross-listing Dept.
教学大纲及教学日历 SYLLABUS
15.
教学目标 Course Objectives
为学生提供基础理论知识以便于学生理解有机分子的结构及反应活性，用实际例子去阐明有机化学在众多学科的重要性。
本课程作为基础有机化学课程的第一部分，随后将要开展 CH206 有机化学 II 。
To provide students with the basic principles to understand the structure and reactivity of organic molecules, with
examples illustrating the role of organic chemistry in daily life and industry. This course serves as the first part of the
complete program on fundamental organic chemistry, to be followed up by CH206 Organic Chemistry II.
16.
预达学习成果 Learning Outcomes
预期学习效果：
1 能够理解有机化学的基本概念，并能够有效的运用其中的专业名词;
2 能够形象地画出正确表示化学分子的三维立体结构式;
3 能够认识、区分并命名手性异构体和非对映异构体
4 能够理解官能团地反应活性;
5 能够掌握反应机理并用以掌握地机理知识应用于解决化学问题;
6 能够应用已知的反应去合成目标分子.
On successful completion of this course, students should be able to:
1 understand basic concepts and employ the vocabulary of organic chemistry;
2 visualize and draw three-dimensional, stereochemically correct representations of organic molecules;
3 recognize, discriminate and name chiral stereoisomers and diastereomers;
4 understand the reactivity of the functional groups;
5 understand reaction mechanisms and apply mechanistic knowledge to solve chemistry problems;
6 apply reactions to the synthesis of target molecules.
17.
课程内容及教学日历 （如授课语言以英文为主，则课程内容介绍可以用英文；如团队教学或模块教学，教学日历须注明
主讲人）
Course Contents (in Parts/Chapters/Sections/Weeks. Please notify name of instructor for course section(s), if
this is a team teaching or module course.)
3
Chapter 1 Introduction and Review
The origins of organic chemistry; Principles of atomic structure; Bond formation: the Octet rule; Lewis structure; Multiple
bonding; Electronegativity and bond polarity; Formal charges; Ionic structure; Resonance; Structural formulas; Molecular
formulas and empirical formulas; Arrhenius acids and bases; Lewis acids and bases. 2 credit hours
第一章 绪论
有机化学的起源；原子结构理论；健的形成；八隅体规则；路易斯结构；多重健；电负性和健极性；形式电荷；离子结
构；共振；分子结构；分子式和实验式；阿伦尼乌斯酸碱；路易斯酸碱。2 个学时
Chapter 2 Structure and Properties of Organic Molecules
Wave properties of electrons in orbitals; Molecular orbitals; Pi bonding; Hybridization and molecular shapes; Drawing
three-dimensional molecules; General rules of hybridization and geometry; Bond rotation; Isomerism; Polarity of bonds
and molecules; Intermolecular forces; Polarity effects on solubilities. 2 credit hours
第二章 有机分子的结构及性质
轨道电子的波性质；分子轨道；Pi 健；杂化轨道和分子构型；化分子的三维结构；杂化轨道和几何结构理论；健的旋转；
同分异构体；分子和健的极性；分子间作用力；相似相溶原理。2 个学时
Chapter 3 Structure and Stereochemistry of alkanes
Nomenclature of alkanes; Physical properties of alkanes; Uses and sources of alkanes; Reactions of alkanes; Structure
and conformations of alkanes; Cycloalkanes; Cyclohexane conformations; Conformations of monosubstituted
cyclohexanes; Conformations of disubstituted cyclohexanes. 4 credit hours
第三章 烷烃的结构和立体化学
烷烃的命名；烷烃的物理性质；烷烃的应用及来源；烷烃的反应；烷烃的结构与构象；环烷烃；环己烷的构象；单取代环
己烷的构象；双取代环己烷的构象。4 个学时
Chapter 4 The Study of Chemical Reactions
Chlorination of methane; The free-radical chain reaction; Equilibrium constants and free energy; Enthalpy and entropy;
Bond-dissociation enthalpies; Enthalpy changes in chlorination; Kinetics and the rate equation; Activation energy and the
temperature dependence of rates; Transition states; Rates of multistep reactions; Temperature dependence of
halogenation; Selectivity in halogenation; The Hammond postulate; Radical inhibitors; Reactive intermediates. 4 credit
hours
第四章 化学反应的研究
氯代甲烷；自由基反应；平衡常数和自由能；焓和熵；焓变；氯代反应中的焓变；动力学和速率方程；活化能与反应速率
的温度依赖；过渡态；多步反应速率；卤代反应的温度依赖；卤代反应的选择性；Hammond 假设；自由基抑制剂；活性
中间体。4 个学时
Chapter 5 Stereochemistry
Chirality; (R) and (S) nomenclature of asymmetric carbon atoms; Optical activity; Racemic mixtures; Enantiomeric
excess and optical purity; Chirality of conformationally mobile systems; Chiral compounds without asymmetric atoms;
Fischer projections; Diastereomers; Stereochemistry of molecules with two or more asymmetric carbons; Meso
compounds; Absolute and relative configuration; Physical properties of diastereomers; Resolution of enantiomers. 4
credit hours
4
第五章 立体化学
手性；不对称碳原子的(R、 (S)命名；光学活性；外消旋混合物；对映体过量和光学纯度；手性构象的移动系统；没有不
对称碳原子的手性化合物；费舍尔投影式；非对映异构体；含两个或更多不对称碳原子分子的立体化学；内消旋化合物；
绝对构型和相对构型；非对映异构体的物理性质；对映异构体的拆分。4 个学时
Chapter 6 Alkyl Halides: Nucleophilic Substitution and Elimination
Nomenclature of alkyl halides; Common uses of alkyl halides; Structure of alkyl halides; Physical properties of alkyl
halides; Preparation of alkyl halides; Reactions of alkyl halides: substitution and elimination; Second-order nucleophilic
substitution: The SN2 reaction; Generality of the SN2 reaction; Factors Affecting SN2 reactions: strength of the
nucleophile; Reactivity of the substrate in SN2 reactions; Stereochemistry of the SN2 reaction; First-order nucleophilic
substitution: the SN1 reaction; Stereochemistry of the SN1 reaction; Rearrangements in SN1 reactions; Comparison of
SN1 and SN2 reactions; First-Order elimination: the El reaction; Positional orientation of elimination: Zaitsev's Rule;
Second-order elimination: the E2 reaction; Stereochemistry of the E2 reaction; Comparison of E1 and E2 elimination
mechanisms. 8 credit hours
第六章 卤代烃：亲核取代与消除
卤代烃的命名；卤代烃的日常用途；卤代烃的结构；卤代烃的物理性质；卤代烃的制备；卤代烃的反应；取代反应与消除
反应；二阶亲核取代；SN2 反应：常见的 SN2 反应；影响 SN2 反应的因素；亲核试剂的强度；SN1：SN1 反应的立体化
学；SN1 反应中的重排现象；比较 SN1 和 SN2 反应；一阶消除反应：El 反应：发生消除反应的位置；扎伊采夫规则；二
阶消除反应；E2 反应的立体化学；比较 El 反应和 E2 反应。8 个学时
Chapter 7 Structure and Synthesis of Alkenes
Nomenclature of alkenes; The orbital description of the alkene double bond; Elements of unsaturation; Commercial
importance of alkenes; Stability of alkenes; Physical properties of alkenes; Alkene synthesis by elimination of alkyl
halides; Alkene synthesis by dehydration of alcohols; Alkene synthesis by high-temperature industrial methods. 4 credit
hours
第七章 烯烃的结构与合成
烯烃的命名；烯烃双健的轨道描述；不饱和元素；烯烃的商业用途；烯烃的稳定性；烯烃的物理性质；通过卤代烃的消除
反应生成烯烃；醇脱水合成烯烃；高温工业合成烯烃。4 个学时
Chapter 8 Reactions of Alkenes
Reactivity of the carbon-carbon double bond; Electrophilic addition to alkenes; Addition of hydrogen halides to alkenes;
Addition of water: hydration of alkenes; Hydration by oxymercuration-demercuration; Alkoxymercuration-
demercuration; Hydroboration of alkenes; Addition of halogens to alkenes; Formation of halohydrins; Catalytic
hydrogenation of alkenes; Addition of carbenes to alkenes; Epoxidation of alkenes; Acid-catalyzed opening of epoxides;
Syn hydroxylation of alkenes; Oxidative cleavage of alkenes; Polymerization of alkenes; Olefin metathesis. 8 credit hours
第八章 烯烃的反应
碳碳双键的活性；烯烃的亲电加成；烯烃的氢卤加成；水的加成；烯烃的水合反应；羟汞化-脱汞水合反应；烷氧汞化-脱
汞；烯烃的硼氢化反应；烯烃的卤素加成；卤代醇的形成；烯烃的催化加氢；卡宾加成生成烯烃；烯烃环氧化；酸催化环
氧化开环反应；烯烃的氢化；烯烃的氧化断裂；烯烃的聚合；烯烃的置换作用。8 个学时
Chapter 9 Alkynes
Nomenclature of alkynes; Physical properties of alkynes; Commercial importance of alkynes; Electronic structure of
alkynes; Acidity of alkynes; Formation of acetylide ions; Synthesis of alkynes from acetylides; Synthesis of alkynes by
5
elimination reactions; Addition reactions of Alkynes; Oxidation of alkynes. 4 credit hours
第九章 炔烃
炔烃的命名；炔烃的物理性质；炔烃的商业价值；炔烃的电子结构；炔烃的酸性；炔基离子的形成；由乙炔合成炔烃；合
成炔烃的消除反应；炔烃的加成反应；炔烃的氧化反应。4 个学时
Chapter 10 Conjugated Systems and Orbital Symmetry
Stabilities of dienes; Molecular orbitals of a conjugated system; Allylic Cations; 1,2- and 1,4-Addition to conjugated
dienes; Kinetic versus thermodynamic control in the addition of HBr to 1,3-Butadiene; Allylic radicals; Molecular orbitals
of the allylic system; Electronic configurations of the allyl radical, cation, and anion; SN2 Displacement reactions of allylic
halides and tosylates; The Diels-Alder reaction; The Diels-Alder as an example of a pericyclic reaction. 6 credit hours
第十章 共轭系统和轨道对称性
双烯类化合物的稳定性；共轭系统的分子轨道；炔基阳离子；双烯化合物的 1,2-和 1,4 加成；HBr 加成到 1,3-Butadiene
的动力学、热力学控制；炔基