有机化学（双语）教学大纲 课程名称有机化学（双语） 英文名称Organic Chemistry 【课程编号】15324X【课程类别】必修 【学分数】2【适用专业】生物科学类基地班 【学时数】64【编写日期】2009-7-20 一、教学目标 1、掌握重要类型有机物（包括开链烃，环烃，卤代烃，醇、酚、醚，醛、酮、醌，羧酸、羧酸衍 生物和取代酸，胺，含硫和含磷有机化合物，杂环化合物)的结构、命名、性质、反应、基本合成 方法和主要用途。熟悉主要官能团相互转换的方法并能用以解决一般合成问题。 2、正确熟练地书写构型式、构象式，理解取代、加成、消去等反应的立体化学过程。 3、正确理解反应的过渡状态、活泼中间体、速率控制和平衡控制等基本概念；掌握各类有机化合 物的主要化学性质，并能将化学性质同各类化合物的转化联系起来；掌握自由基反应、亲电取代反 应、亲核取代反应、亲电加成反应、亲核加成反应、消除反应和重排反应等主要类型的反应机理； 掌握诱导效应和共轭效应等电子效应的一般理论及其应用。 4、了解有机化学与生命化学和分子生物学之间的关系，能初步用有机化学的知识理解生命化学和 分子生物学中所发生的现象和变化；初步了解质谱、红外光谱、紫外光谱和质子核磁共振谱的基本 原理及在各类有机化学中的简单应用。 5、通过使用英文原版教材进行双语教学，熟悉重要有机物和有机反应的英文名称，具备基本的阅读 英文有机化学文献的能力。 二、教学内容和学时分配 (一）Chapter1 Introduction and Review2学时 主要内容： 1.1 The Origins of Organic Chemistry 1.2 Principles of Atomic Structure 1.3 Bond Formation:The Octet Rule 1.4 Lewis Structures 1.5 Multiple Bonding 1.6 Electronegativity and Bond Polarity 1.7 Formal Charges 1.8 lonic Structures 1.9 Resonance 1.10 Structural Formulas 1.11 Molecular Formulas and Empirical Formulas 1.12 Arrhenius Acids and Bases
有机化学（双语）教学大纲 课程名称有机化学 (双语) 英文名称Organic Chemistry 【课程编号】15324X 【课程类别】必修 【学分数】2 【适用专业】生物科学类基地班 【学时数】64 【编写日期】2009-7-20 一、教学目标 １、掌握重要类型有机物（包括开链烃，环烃，卤代烃，醇、酚、醚，醛、酮、醌，羧酸、羧酸衍 生物和取代酸，胺，含硫和含磷有机化合物，杂环化合物）的结构、命名、性质、反应、基本合成 方法和主要用途。熟悉主要官能团相互转换的方法并能用以解决一般合成问题。 ２、正确熟练地书写构型式、构象式，理解取代、加成、消去等反应的立体化学过程。 ３、正确理解反应的过渡状态、活泼中间体、速率控制和平衡控制等基本概念；掌握各类有机化合 物的主要化学性质，并能将化学性质同各类化合物的转化联系起来；掌握自由基反应、亲电取代反 应、亲核取代反应、亲电加成反应、亲核加成反应、消除反应和重排反应等主要类型的反应机理； 掌握诱导效应和共轭效应等电子效应的一般理论及其应用。 ４、了解有机化学与生命化学和分子生物学之间的关系，能初步用有机化学的知识理解生命化学和 分子生物学中所发生的现象和变化；初步了解质谱、红外光谱、紫外光谱和质子核磁共振谱的基本 原理及在各类有机化学中的简单应用。 5、通过使用英文原版教材进行双语教学，熟悉重要有机物和有机反应的英文名称，具备基本的阅读 英文有机化学文献的能力。 二、教学内容和学时分配 （一）Chapter 1 Introduction and Review 2 学时 主要内容： 1.1 The Origins of Organic Chemistry 1.2 Principles of Atomic Structure 1.3 Bond Formation: The Octet Rule 1.4 Lewis Structures 1.5 Multiple Bonding 1.6 Electronegativity and Bond Polarity 1.7 Formal Charges 1.8 Ionic Structures 1.9 Resonance 1.10 Structural Formulas 1.11 Molecular Formulas and Empirical Formulas 1.12 Arrhenius Acids and Bases
1.13 Br.nsted-Lowry Acids and Bases 1.14 Lewis Acids and Bases 教学要求： 掌握以下教学内容：Definitions;:Atomic Structure and Electronic Configurations;Bond Formation and Lewis Structures:Dipole Moment and Molecular Polarity:Chemical Formulas;Lewis Acids and Bases. (二)Chapter2 Structure and Properties of Organic Molecules2学时 主要内容： 2.1 Wave Properties of Electrons in Orbitals 2.2 Molecular Orbitals 2.3 Pi Bonding 2.4 Hybridization and Molecular Shapes 2.5 Drawing Three-Dimensional Molecules 2.6 General Rules of Hybridization and Geometry 2.7 Bond Rotation 2.8 Isomerism 2.9 Polarity of Bonds and Molecules 2.10 Intermolecular Forces 2.11 Polarity Effects on Solubilities 2.12 Hydrocarbons 2.13 Organic Compounds Containing Oxygen 2.14 Organic Compounds Containing Nitrogen 教学要求： 掌握以下教学内容：Molecular Orbital,Pi Bonding;Hybrid Orbitals;Isomerism;Bond and Molecular Dipole Moments:Intermolecular Forces;Boiling Points and Solubility:Classes of Compounds ()Chapter 3 Brief Introduction and Nomenclature of Organic Compounds4 主要内容： 3.1 Classification Functional groups of O.Cs. 3.2 Nomenclature of hydrocarbons;Alkanes,Alkenes,Alkynes,Aromatic hydrocarbons 3.3 Nomenclature of O.Cs.containing oxygen Alcohols,Ehters,Aldehydes and ketones,Carboxylic acids,Carboxylic acid derivatives 3.4 Nomenclature of O.Cs.containing nitrogen Amines,Nitriles,Acid anhlides &acid anhydrides 3.5 Nomenclature of Multifunctional compounds 教学要求：
1.13 Br.nsted-Lowry Acids and Bases 1.14 Lewis Acids and Bases 教学要求： 掌握以下教学内容：Definitions; Atomic Structure and Electronic Configurations; Bond Formation and Lewis Structures; Dipole Moment and Molecular Polarity; Chemical Formulas; Lewis Acids and Bases. （二）Chapter 2 Structure and Properties of Organic Molecules 2 学时 主要内容： 2.1 Wave Properties of Electrons in Orbitals 2.2 Molecular Orbitals 2.3 Pi Bonding 2.4 Hybridization and Molecular Shapes 2.5 Drawing Three-Dimensional Molecules 2.6 General Rules of Hybridization and Geometry 2.7 Bond Rotation 2.8 Isomerism 2.9 Polarity of Bonds and Molecules 2.10 Intermolecular Forces 2.11 Polarity Effects on Solubilities 2.12 Hydrocarbons 2.13 Organic Compounds Containing Oxygen 2.14 Organic Compounds Containing Nitrogen 教学要求： 掌握以下教学内容：Molecular Orbital; Pi Bonding; Hybrid Orbitals; Isomerism; Bond and Molecular Dipole Moments; Intermolecular Forces; Boiling Points and Solubility; Classes of Compounds. （三）Chapter 3 Brief Introduction and Nomenclature of Organic Compounds 4 学时 主要内容： 3.1 Classification & Functional groups of O.Cs. 3.2 Nomenclature of hydrocarbons；Alkanes，Alkenes，Alkynes，Aromatic hydrocarbons 3.3 Nomenclature of O.Cs. containing oxygen Alcohols，Ehters，Aldehydes and ketones，Carboxylic acids，Carboxylic acid derivatives 3.4 Nomenclature of O.Cs. containing nitrogen Amines，Nitriles，Acid anhlides & acid anhydrides 3.5 Nomenclature of Multifunctional compounds 教学要求：
掌握以下教学内容：Functional group,Classification,.UPAC Names (四)Chapter3 Structure and Stereochemistry of Alkanes3学时 主要内容： 4.1 Classification of Hydrocarbons 4.2 Molecular Formulas of Alkanes 4.3 Nomenclature of Alkanes 4.4 Physical Properties of Alkanes 4.5 Uses and Sources of Alkanes 4.6 Reactions of Alkanes 4.7 Structure and Conformations of Alkanes 4.8 Conformations of Butane 4.9 Conformations of Higher Alkanes 4.10 Cycloalkanes 4.11 Cis-trans Isomerism in Cycloalkanes 4.12 Stabilities of Cycloalkanes;Ring Strain 4.13 Cyclohexane Conformations 4.14 Conformations of Monosubstituted Cyclohexanes 4.15 Conformations of Disubstituted Cyclohexanes 4.16 Bicyclic Molecules 教学要求： 掌握以下教学内容：Alkanes,.saturated hydrocarbons,Straight-chain or branched-chain alkanes, IUPAC rules of nomenclature,Isomers,Constitutional isomers,Cycloalkanes,Cis-trans isomers, Angle strain,Torsional strain,Van der Waals strain,Conformation and conformational analysis Staggered, eclipsed,anti,syn,gauche conformation,Chair,skew boat,boat conformation,Axial and equatorial Stereoisomers,cis-and trans stereoisomers.Spirocyclic,bicyclic (伍)Chapter5 The Study of Chemical Reactions1学时 主要内容 5.1 Introduction 5.2 Chlorination of Methane 5.3 The Free-Radical Chain Reaction 5.4 Equilibrium Constants and Free Energy 5.5 Enthalpy and Entropy 5.6 Bond-Dissociation Enthalpies
掌握以下教学内容：Functional group，Classification。IUPAC Names （四）Chapter 3 Structure and Stereochemistry of Alkanes 3 学时 主要内容： 4.1 Classification of Hydrocarbons 4.2 Molecular Formulas of Alkanes 4.3 Nomenclature of Alkanes 4.4 Physical Properties of Alkanes 4.5 Uses and Sources of Alkanes 4.6 Reactions of Alkanes 4.7 Structure and Conformations of Alkanes 4.8 Conformations of Butane 4.9 Conformations of Higher Alkanes 4.10 Cycloalkanes 4.11 Cis-trans Isomerism in Cycloalkanes 4.12 Stabilities of Cycloalkanes; Ring Strain 4.13 Cyclohexane Conformations 4.14 Conformations of Monosubstituted Cyclohexanes 4.15 Conformations of Disubstituted Cyclohexanes 4.16 Bicyclic Molecules 教学要求： 掌握以下教学内容：Alkanes, saturated hydrocarbons, Straight-chain or branched-chain alkanes, IUPAC rules of nomenclature, Isomers, Constitutional isomers, Cycloalkanes, Cis-trans isomers, Angle strain, Torsional strain, Van der Waals strain, Conformation and conformational analysis, Staggered, eclipsed, anti, syn, gauche conformation, Chair, skew boat, boat conformation, Axial and equatorial, Stereoisomers, cis- and trans stereoisomers, Spirocyclic, bicyclic （五）Chapter 5 The Study of Chemical Reactions 1 学时 主要内容： 5.1 Introduction 5.2 Chlorination of Methane 5.3 The Free-Radical Chain Reaction 5.4 Equilibrium Constants and Free Energy 5.5 Enthalpy and Entropy 5.6 Bond-Dissociation Enthalpies
5.7 Enthalpy Changes in Chlorination 5.8 Kinetics and the Rate Equation 5.9 Activation Energy and the Temperature Dependence of Rates 5.10 Transition States 5.11 Rates of Multistep Reactions 5.12 Temperature Dependence of Halogenation 5.13 Selectivity in Halogenation 5.14 The Hammond Postulate 5.15 Radical Inhibitors 5.16 Reactive Intermediates 教学要求： 掌握以下教学内容：Reactions:Addition,.Elimination,Substitution,Rearrangement;Mechanisms Radical,Polar,Nucleophile and electrophile,Transition states and intermediates (六)Chapter6 Stereochemistry4学时 主要内容： 6.1 Introduction 6.2 Chirality 6.3(R)and(S)Nomenclature of Asymmetric Carbon Atoms 6.4 Optical Activity 6.5 Biological Discrimination of Enantiomers 6.6 Racemic Mixtures 6.7 Enantiomeric Excess and Optical Purity 6.8 Chirality of Conformationally Mobile Systems 6.9 Chiral Compounds without Asymmetric Atoms 6.10 Fischer Projections 6.11 Diastereomers 6.12 Stereochemistry of Molecules with Two or More Asymmetric Carbons 6.13 Meso Compounds 6.14Absolute and Relative Configuration 6.15 Physical Properties of Diastereomers 6.16 Resolution of Enantiomers 教学要求： 掌握以下教学内容：Stereochemistry,Chiral enantiomers,Chirality center,,Optical activity,.Optical rotations,Racemic mixture configuration,R and S of the Cahn-Ingold-Prelog notational system
5.7 Enthalpy Changes in Chlorination 5.8 Kinetics and the Rate Equation 5.9 Activation Energy and the Temperature Dependence of Rates 5.10 Transition States 5.11 Rates of Multistep Reactions 5.12 Temperature Dependence of Halogenation 5.13 Selectivity in Halogenation 5.14 The Hammond Postulate 5.15 Radical Inhibitors 5.16 Reactive Intermediates 教学要求： 掌握以下教学内容：Reactions: Addition, Elimination, Substitution, Rearrangement; Mechanisms: Radical,Polar, Nucleophile and electrophile, Transition states and intermediates （六）Chapter 6 Stereochemistry 4 学时 主要内容： 6.1 Introduction 6.2 Chirality 6.3 (R) and (S) Nomenclature of Asymmetric Carbon Atoms 6.4 Optical Activity 6.5 Biological Discrimination of Enantiomers 6.6 Racemic Mixtures 6.7 Enantiomeric Excess and Optical Purity 6.8 Chirality of Conformationally Mobile Systems 6.9 Chiral Compounds without Asymmetric Atoms 6.10 Fischer Projections 6.11 Diastereomers 6.12 Stereochemistry of Molecules with Two or More Asymmetric Carbons 6.13 Meso Compounds 6.14 Absolute and Relative Configuration 6.15 Physical Properties of Diastereomers 6.16 Resolution of Enantiomers 教学要求： 掌握以下教学内容：Stereochemistry, Chiral enantiomers, Chirality center, Optical activity, Optical rotations, Racemic mixture configuration, R and S of the Cahn–Ingold–Prelog notational system
Fischer projection,Diastereomers meso forms,Prochiral and prochirality,Resolution of enantiomers ()Chapter 7 Alkyl Halides:Nucleophilic Substitution and Elimination 4 主要内容： 7.1 Introduction 7.2 Nomenclature of Alkyl Halides 7.3 Common Uses of Alkyl Halides 7.4 Structure of Alkyl Halides 7.5 Physical Properties of Alkyl Halides 7.6 Preparation of Alkyl Halides 7.7 Reactions of Alkyl Halides:Substitution and Elimination 7.8 Second-Order Nucleophilic Substitution:The SN2 Reaction 7.9 Generality of the SN2 Reaction 7.10 Factors Affecting SN2 Reactions:Strength of the Nucleophile 7.11 Reactivity of the Substrate in SN2 Reactions 7.12 Stereochemistry of the SN2 Reaction 7.13 First-Order Nucleophilic Substitution:The SN1 Reaction 7.14 Stereochemistry of the SNI Reaction 7.15 Rearrangements in SN1 Reactions 7.16 Comparison of SN1 and SN2 Reactions 7.17 First-Order Elimination:The E1 Reaction 7.18 Positional Orientation of Elimination:Zaitsev's Rule 7.19 Second-Order Elimination:The E2 Reaction 7.20 Stereochemistry of the E2 Reaction 7.21 Comparison of El and E2 Elimination Mechanisms 教学要求： 掌握以下教学内容：SN1 reactions governed by electronic factors,.the relative stabilities of carbocation intermediates,SN2 reactions governed by steric factors,the relative ease of approach of the nucleophile to the site of reaction,E2 mechanism,E1 mechanism,carbocation rearrangements (八)Chapter8 Structure and synthesis of Alkenes2学时 主要内容： 8.1 Introduction 8.2 The Orbital Description of the Alkene Double Bond
Fischer projection, Diastereomers meso forms, Prochiral and prochirality, Resolution of enantiomers （七）Chapter 7 Alkyl Halides: Nucleophilic Substitution and Elimination 4 学时 主要内容： 7.1 Introduction 7.2 Nomenclature of Alkyl Halides 7.3 Common Uses of Alkyl Halides 7.4 Structure of Alkyl Halides 7.5 Physical Properties of Alkyl Halides 7.6 Preparation of Alkyl Halides 7.7 Reactions of Alkyl Halides: Substitution and Elimination 7.8 Second-Order Nucleophilic Substitution: The SN2 Reaction 7.9 Generality of the SN2 Reaction 7.10 Factors Affecting SN2 Reactions: Strength of the Nucleophile 7.11 Reactivity of the Substrate in SN2 Reactions 7.12 Stereochemistry of the SN2 Reaction 7.13 First-Order Nucleophilic Substitution: The SN1 Reaction 7.14 Stereochemistry of the SNl Reaction 7.15 Rearrangements in SN1 Reactions 7.16 Comparison of SN1 and SN2 Reactions 7.17 First-Order Elimination: The E1 Reaction 7.18 Positional Orientation of Elimination: Zaitsev’s Rule 7.19 Second-Order Elimination: The E2 Reaction 7.20 Stereochemistry of the E2 Reaction 7.21 Comparison of El and E2 Elimination Mechanisms 教学要求： 掌握以下教学内容：SN1 reactions governed by electronic factors, the relative stabilities of carbocation intermediates, SN2 reactions governed by steric factors, the relative ease of approach of the nucleophile to the site of reaction, E2 mechanism, E1 mechanism, carbocation rearrangements （八）Chapter 8 Structure and synthesis of Alkenes 2 学时 主要内容： 8.1 Introduction 8.2 The Orbital Description of the Alkene Double Bond