《有机化学》课程教学大纲

一、课程基本信息

二、课程目标

（一）总体目标：

 Introduction to basic organic chemistry in terms of the principles of organic molecular structures, stereochemistry, functional groups, basic organic reactions and their mechanisms. In addition to introducing some fundamental principles of structure and bonding, polar covalent bonds, as well as acids and bases, the course covers the characteristic properties, synthesis, and reactivity of alkanes, alkenes, benzene and other aromatic compounds, halides, alcohols, aldehydes, ketones, carboxylic acids and their derivatives.

（二）课程目标：

课程目标1：

 1．1 Teaching students how important the study of organic chemistry is in the students educations, carrier and life?

1. 2 Stimulate students' innovative consciousness.

1. 3 Cultivate students' ability to examine and solve problems related to the organic compounds in future engineering practice.

课程目标2：

 2．1 Master the basic concepts, principles and skills of  organic chemistry at the university level

 2．2

（三）课程目标与毕业要求、课程内容的对应关系

表1：课程目标与课程内容、毕业要求的对应关系表

（大类基础课程、专业教学课程及开放选修课程按照本科教学手册中各专业拟定的毕业要求填写“对应毕业要求”栏。通识教育课程含通识选修课程、新生研讨课程及公共基础课程，面向专业为工科、师范、医学等有专业认证标准的专业，按照专业认证通用标准填写“对应毕业要求”栏；面向其他尚未有专业认证标准的专业，按照本科教学手册中各专业拟定的毕业要求填写“对应毕业要求”栏。）

三、教学内容

第一章 - Structure and Bonding

1.教学目标 :

This chapter presents a short overview of organic chemistry as a major branch of chemistry. By building on the basics of general chemistry, the ability of carbon to produce a wide range of complex molecular types is highlighted. The purpose of the chapter is to introduce functional groups, structure drawing, molecular electronic effects, and the prediction of molecular shape. The relationship between physical properties and structure is also briefly considered.

2.教学重难点：

3.教学内容:

The periodic table; Bonding Lewis structures; Isomers; Exceptions to the octet rule; Resonance; Determining molecular shape; Drawing organic structures; Hybridization; Ethane, ethylene, and acetylene; Bond length and bond strength; Electronegativity and bond polarity; Polarity of molecules.

4.教学方法:

Lecture method; case teaching method; practice method; independent learning method; discussion method

5.教学评价:

Classwork, matched problems, homework and discussions.

第二章 - Acids and Bases

1.教学目标 :

This chapter introduces the concepts of acidity and basicity as they relate to organic molecules. Acids and bases are defined in terms of Brønsted–Lowry and Lewis criteria. Expressions for acidity and basicity are discussed and applied to a study of carboxylic acids. The influence of factors such as inductive and delocalization/resonance effects on acidity are studied. The same concepts are applied to other functional classes in order to understand the wide range of acidity possible within organic molecules.

2.教学重难点：

3.教学内容:

 Brønsted–Lowry acids and bases; Reactions of Brønsted–Lowry acids and bases; Acid strength and pKa; Predicting the outcome of acid-base reactions; Factors that determine acid strength; Common acids and bases; Aspirin; Lewis acids and bases

4.教学方法:

Lecture method; case teaching method; practice method; independent learning method; discussion method

5.教学评价:

Classwork, matched problems, homework and discussions.

第三章 - Introduction to Organic Molecules

and Functional Groups

1.教学目标 :

This chapter takes an initial look at the structure and representation of functional groups. The principles of the unambiguous systematic classification and naming of organic compounds are introduced. The importance of these for accurate information transfer is highlighted. Common functional classes are detailed and, where needed, three-dimensional diagrams, oxidation states, and physical properties are introduced.

2.教学重难点：

3.教学内容:

Functional groups; An overview of functional groups; Intermolecular forces; Physical properties; Application: Vitamins; Application of solubility: Soap; Application: The cell membrane; Functional groups and reactivity; Biomolecules

4.教学方法:

Lecture method; case teaching method; practice method; independent learning method; discussion method

5.教学评价:

Classwork, matched problems, homework and discussions.

第四章 - Alkanes

1.教学目标 :

 In Chapter 4, we apply the principles of bonding, shape, and reactivity discussed in Chapters 1–3 to our first family of organic compounds, the alkanes. Because alkanes have no functional group, they are much less reactive than other organic compounds, and for this reason, much of Chapter 4 is devoted to learning how to name and draw them, as well as to understanding what happens when rotation occurs about their carbon–carbon single bonds.

2.教学重难点：

3.教学内容:

Alkanes—An introduction; Cycloalkanes; An introduction to nomenclature Naming alkanes; Naming cycloalkanes; Common names; Natural occurrence of alkanes; Properties of alkanes; Conformations of acyclic alkanes—Ethane; Conformations of butane; An introduction to cycloalkanes; Cyclohexane Substituted cycloalkanes; Oxidation of alkanes; Lipids—Part 1.

4.教学方法:

Lecture method; case teaching method; practice method; independent learning method; discussion method

5.教学评价:

Classwork, matched problems, homework and discussions.

第五章 - Stereochemistry

1.教学目标 :

 In Chapter 5, we examine the “handedness” of molecules, and learn about the importance of the three-dimensional shape of a molecule.

2.教学重难点：

3.教学内容:

Starch and cellulose; The two major classes of isomers; Looking glass chemistry—Chiral and achiral molecules; Stereogenic centers Stereogenic centers in cyclic compounds; Labeling stereogenic centers with R or S; Diastereomers Meso compounds R and S assignments in compounds with two or more stereogenic centers; Disubstituted cycloalkanes Isomers—A summary Physical properties of stereoisomers; Chemical properties of enantiomers.

4.教学方法:

Lecture method; case teaching method; practice method; independent learning method; discussion method

5.教学评价:

Classwork, matched problems, homework and discussions.

第六章 – Understanding organic reactions

1.教学目标 :

This chapter discusses factors that affect the reactivity of organic molecules. Bond breaking and making are shown in terms of the bonding electrons, and these are followed using curly arrows. The formation and stability of reactive species—radicals, anions and cations—are discussed in terms of inductive and delocalization/resonance effects. The nature of electrophiles and nucleophiles is detailed. Primary reaction types—addition, elimination, substitution, and rearrangement—are introduced, along with the description of reaction mechanisms and energy diagrams. Finally, the REDOX concept as applied to organic molecules is described.

2.教学重难点：

3.教学内容:

Writing equations for organic reactions; Kinds of organic reactions; Bond breaking and bond making; Bond dissociation energy; Thermodynamics; Enthalpy and entropy; Energy diagrams; Energy diagram for a two-step reaction mechanism; Kinetics; Catalysts; Enzymes

4.教学方法:

Lecture method; case teaching method; practice method; independent learning method; discussion method

5.教学评价:

Classwork, matched problems, homework and discussions.

第七章 – Alkyl Halides and Nucleophilic Substitution

1.教学目标 :

 This is the first of three chapters dealing with an in-depth study of the organic reactions of compounds containing C–Z σ bonds, where Z is an element more electronegative than carbon. In Chapter 7, we learn about alkyl halides and one of their characteristic reactions, nucleophilic substitution, a key step in the synthesis of several useful drugs and natural products.

2.教学重难点：

3.教学内容:

Introduction to alkyl halides; Nomenclature Properties of alkyl halides; Interesting alkyl halides; The polar carbon–halogen bond; General features of nucleophilic substitution; The leaving group; The nucleophile; Possible mechanisms for nucleophilic substitution; Two mechanisms for nucleophilic substitution; The SN2 mechanism; The SN1 mechanism; Carbocation stability; The Hammond postulate; When is the mechanism SN1 or SN2? Biological nucleophilic substitution; Vinyl halides and aryl halides; Organic synthesis

4.教学方法:

Lecture method; case teaching method; practice method; independent learning method; discussion method

5.教学评价:

Classwork, matched problems, homework and discussions.

第八章 – Alkyl Halides and Elimination Reactions

1.教学目标 :

 By the end of Chapter 8, you will have learned four different reaction mechanisms, two for nucleophilic substitution (SN1 and SN2) and two for elimination (E1 and E2).

2.教学重难点：

3.教学内容:

General features of elimination; Alkenes—The products of elimination reactions; The mechanisms of elimination; The E2 mechanism; The Zaitsev rule; The E1 mechanism; SN1 and E1 reactions; Stereochemistry of the E2 reaction; When is the mechanism E1 or E2? E2 reactions and alkyne synthesis; When is the reaction SN1, SN2, E1, or E2?

4.教学方法:

Lecture method; case teaching method; practice method; independent learning method; discussion method

5.教学评价:

Classwork, matched problems, homework and discussions.

第九章 – Alcohols, Ethers, and Related Compounds

1.教学目标 :

 In Chapter 9, we take the principles learned in Chapters 7 and 8 about leaving groups, nucleophiles, and bases, and apply them to alcohols, ethers, and epoxides, three new functional groups that contain polar C—O bonds. The hydroxy group (OH) of an alcohol is especially common in many natural products, and the reactions of alcohols are widely used in organic synthesis. In Chapter 9, you will discover that all of the reactions follow one of the four mechanisms introduced in Chapters 7 and 8—SN1, SN2, E1, or E2—so there are no new general mechanisms to learn. Later in the chapter, we will also examine thiols (RSH) and sulfides (R2S), sulfur analogues of alcohols and ethers, respectively. These functional groups play a key role in the chemistry of biomolecules, especially the proteins

2.教学重难点：

3.教学内容:

Introduction; Structure and bonding; Nomenclature; Properties of alcohols, ethers, and epoxides; Interesting alcohols, ethers, and epoxides; Preparation of alcohols, ethers, and epoxides; General features—Reactions of alcohols, ethers, and epoxides; Dehydration of alcohols to alkenes; Carbocation rearrangements;

4.教学方法:

Lecture method; case teaching method; practice method; independent learning method; discussion method

5.教学评价:

Classwork, matched problems, homework and discussions.

四、学时分配

表2：各章节的具体内容和学时分配表

五、教学进度

表3：教学进度表

六、教材及参考书目

1.  Organic Chemistry, 6rd edition, ISBN 978-1-260-11910-7, by Janice Gorzynski Smith, published by Mc Graw Hill © 2019.

七、教学方法

 In the teaching process of this course, the teaching method highlights the heuristic teaching method. Through the introduction of the teaching content, combined with the example explanation and case analysis, the students are guided to think more, ask more questions and discuss more.

八、考核方式及评定方法

（一）课程考核与课程目标的对应关系

表4：课程考核与课程目标的对应关系表

（二）评定方法

1．评定方法

（例：平时成绩：10%，期中考试：30%，期末考试60%，按课程考核实际情况描述）

2．课程目标的考核占比与达成度分析

表5：课程目标的考核占比与达成度分析表（五号宋体）

（三）评分标准 （小四号黑体）