课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry：Paula. Y. Bruice,

7th edition

授课年级

2019全英文药学班

授课章节

Electronic structure and bonding

授课时间

150分钟

一、教学目标：含知识目标、技能（能力）目标

1．知识目标：

(1) Know the structure of an atom

(2) Learn ionic and covalent bonds

(3) Understand atomic orbitals and molecular orbitals

(4) Know the formation of single bonds, double bonds and triple bonds

2.技能（能力）目标：

(1) Learn basic terms in organic chemistry

(2) Be able to draw the electronic configuration and Lewis structures

(3) Understand the atomic and molecular orbital theory

(4) Be able to predict the hybridization

二、授课内容（依据教学大纲）及时间分配

1. The structure of an atom (5 min)

2. How the electrons in an atom are distributed (10 min)

3. Ionic and covalent bonds (15 min)

4.How the structure of a compound is represented (15 min)

5. Atomic orbitals (10 min)

6. An introduction to molecular orbital theory (20 min)

7. How single bonds are formed in organic compounds (20 min)

8. How a double bond is formed: the bonds in ethene (15 min)

9. How a triple bond is formed: the bonds in ethyne (10 min)

10. The bonds in the methyl cation, the methyl radical, and the methyl anion (10 min)

11. The bonds in ammonia and in the ammonium ion (10 min)

12. Review (10 min)

三、教学重点与难点

1．教学重点

(1) covalent bonds  

(2) Lewis structures  

(3) atomic orbitals, molecular orbitals and hybrid orbitals

(4) the formation of single bonds, double bonds and triple bonds

2.教学难点

(1) atomic orbital theory and molecular orbital theory

(2) the formation of single bonds, double bonds and triple bonds

(3) hybridization

四、教学方法选择

1.理论课堂教学

A.多媒体教学：（简要列出本章节多媒体教学设计特点及优势）

(1) List the detailed schematic diagram  

(2) Review the major concepts and materials covering the lectures

(3) Work on problems with students together to emphasize the basic knowledge covered in the lectures

B.互动教学：（根据实际情况列出案例/实例讨论、分析讨论、分组讨论、翻转课堂等互动教学内容标题）

(1) Ask questions during the lectures

(2) Solve problems together with students

2.实验课教学

No applicable

五、更新或补充内容提要

课后总结：按照实际进度对知识点分详略进行讲解

Emphasize the key knowledge and adjust the amount of materials in each section.

六、复习思考题

1. Write electronic configurations for chlorine (atomic number 17), bromine (atomic number 35), and iodine (atomic number 53).  

2. Draw two Lewis structures for C₂H₆O.

3. What orbitals are used to form the 10 sigma bonds in propane (CH₃CH₂CH₃)?

4. Explain why a  bond formed by overlap of an s orbital with an sp³ orbital of carbon is stronger.

5. Predict the approximate bond angles in the methyl cation.  

6.Which of the bonds in a carbon–oxygen double bond has more effective orbital–orbital overlap, the  bond or the  bond?

七、学习资源、课外自主学习参考

(可以列出供学生进一步学习、拓展本章节内容的网站、著作、期刊的名称及内容等)

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry：Paula. Y. Bruice,

7th edition

授课年级

2019全英文药学班

授课章节

1.  Electronic structure and bonding

2.  Acids and Bases

授课时间

100分钟

一、教学目标：含知识目标、技能（能力）目标

1．知识目标：

(1) Understand atomic orbitals and molecular orbitals

(2) Know acid-base theory  

(3) Know the strength of an acid

2.技能（能力）目标：

(1) Be able to predict the hybridization

(2) Be able to draw the electronic configuration and Lewis structures

(3) Be able to compare the acid strength

二、授课内容（依据教学大纲）及时间分配

1. The bonds in water (10 min)

2. The bond in a hydrogen halide (10 min)

3. Hybridization and molecular geometry (10 min)

4. Summary: hybridization, bond lengths, bond strengths, and bond angles (15 min)

5. The dipole moments of molecules (5 min)

6.  An introduction to acids and bases (5 min)

7. pk_a and pH (10 min)

8. Organic acids and bases (10 min)

9. How to predict the outcome of an acid–base reaction (5 min)

10. How to determine the position of equilibrium (5 min)

11. How the structure of an acid affects its pk_a value (10 min)

12. Review (5 min)

三、教学重点与难点

1．教学重点

(1) hybridization and molecular geometry

(2) pk_a and pH

(3) the position of equilibrium in an acid–base reaction

2.教学难点

(1) hybridization and molecular geometry

(2) acid strength

四、教学方法选择

1.理论课堂教学

A.多媒体教学：（简要列出本章节多媒体教学设计特点及优势）

(1) List the detailed schematic diagram  

(2) Review the major concepts and materials covering the lectures

(3) Work on problems with students together to emphasize the basic knowledge covered in the lectures

B.互动教学：（根据实际情况列出案例/实例讨论、分析讨论、分组讨论、翻转课堂等互动教学内容标题）

(1) Ask questions during the lectures

(2) Solve problems together with students

2.实验课教学

No applicable

五、更新或补充内容提要

课后总结：按照实际进度对知识点分详略进行讲解

Emphasize the key knowledge and adjust the amount of materials in each section.

六、复习思考题

1. Predict the relative lengths and strengths of the carbon–halogen bonds in CH₃F, CH₃Cl, and CH₃Br.

2. Would you expect a C-C  bond formed by sp²–sp² overlap to be stronger or weaker than a C-C  bond formed by sp³–sp³ overlap?

3. Which is a stronger base, CH₃COO^ or HCOO^? (The pK_a of CH3COOH is 4.8; the pK_a of HCOOH is 3.8.)

4. Which of the halide ions (F^, Cl^, Br^, and I^) is the most stable base?  

七、学习资源、课外自主学习参考

(可以列出供学生进一步学习、拓展本章节内容的网站、著作、期刊的名称及内容等)

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry：Paula. Y. Bruice,

7th edition

授课年级

2019全英文药学班

授课章节

1.  Acids and Bases

2.  An Introduction to Organic compounds

授课时间

150分钟

一、教学目标：含知识目标、技能（能力）目标

1．知识目标：

(1) Understand the delocalization of electrons

(2) Learn the buffer solutions  

(3) Know the common names of alkanes, cycloalkanes, alkyl halides, ethers, alcohols and amines

(4) Know the systematic names of alkanes, cycloalkanes, alkyl halides, ethers, alcohols and amines

2.技能（能力）目标：

(1) Be able to calculate the pH values

(2) Be able to differentiate the substituent and functional group

(3) Be able to draw the structures for specific names.

(4) Be able to draw the common and systematic names for specific structures.

二、授课内容（依据教学大纲）及时间分配

1. How substituents affect the strength of an acid (10 min)

2. An introduction to delocalized electrons (10 min)

3. A summary of the factors that determine acid strength (10 min)

4. How pH affects the structure of an organic compound (10 min)

5. Buffer solutions (5 min)

6. Lewis acids and bases (5 min)

7. An introduction to organic compounds (10 min)

8. How alkyl substituents are named (10 min)

9. The nomenclature of alkanes (15 min)

10. The nomenclature of cycloalkanes (15 min)

11.The nomenclature of alkyl halides (10 min)

12. The nomenclature of ethers (10 min)

13. The nomenclature of alcohols (10 min)

14. The nomenclature of amines (10 min)

15. Review (10 min)

三、教学重点与难点

1．教学重点

(1) electrons delocalization

(2) the factors that determine acid strength

(3) the substituent and functional group

(4) common names of alkanes, cycloalkanes, alkyl halides, ethers, alcohols and amines

(5) systematic nomenclature of alkanes, cycloalkanes, alkyl halides, ethers, alcohols and amines

2.教学难点

(1) electrons delocalization

(2) differentiate the substituent and functional group  

(3) systematic nomenclature of alkanes, cycloalkanes, alkyl halides, ethers, alcohols and amines.

(4) constitutional isomers

四、教学方法选择

1.理论课堂教学

A.多媒体教学：（简要列出本章节多媒体教学设计特点及优势）

(1) List the detailed schematic diagram  

(2) Review the major concepts and materials covering the lectures

(3) Work on problems with students together to emphasize the basic knowledge covered in the lectures

B.互动教学：（根据实际情况列出案例/实例讨论、分析讨论、分组讨论、翻转课堂等互动教学内容标题）

(1) Ask questions during the lectures

(2) Solve problems together with students

2.实验课教学

No applicable

五、更新或补充内容提要

课后总结：按照实际进度对知识点分详略进行讲解

Emphasize the key knowledge and adjust the amount of materials in each section.

六、复习思考题

1. Calculate the pH values of a 1.0 M solution of acetic acid (pK_a = 4.76).

2. Draw the structures and name the constitutional isomers with molecular formula C₄H₉Br.

3. Draw a condensed and a skeletal structure for 3,4-diethyl-2-methylheptane.

4. What is the systematic name for CH₃CH₂OCH₂CH₃?

5. Write the structures of all the tertiary alcohols with molecular formula C₆H₁₄O and give each a systematic name.  

七、学习资源、课外自主学习参考

(可以列出供学生进一步学习、拓展本章节内容的网站、著作、期刊的名称及内容等)

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry：Paula. Y. Bruice,

7th edition

授课年级

2019全英文药学班

授课章节

An Introduction to Organic compounds

授课时间

100分钟

一、教学目标：含知识目标、技能（能力）目标

1．知识目标：

(1) Learn the physical properties of alkanes, alkyl halides, alcohols, ethers, and amines.

(2) Know the Newman projection of ethane and cyclohexane.

(3) Know the conformers of cyclohexane.

(4) Know the conformers of substituted cyclohexanes.

2.技能（能力）目标：

(1) Be able to compare the physical properties.

(2) Be able to draw Newman projections.

(3) Be able to draw the conformers of substituted cyclohexanes.

二、授课内容（依据教学大纲）及时间分配

1. The structures of alkyl halides, alcohols, ethers, and amines (10 min)

2. The physical properties of alkanes, alkyl halides, alcohols, ethers, and amines (15 min)

3. Rotation occurs about carbon–carbon single bonds (15 min)

4. Some cycloalkanes have angle strain (10 min)

5.Conformers of cyclohexane (20 min)

6. Conformers of monosubstituted cyclohexanes (10 min)

7. Conformers of disubstituted cyclohexanes (10 min)

8. Fused cyclohexane rings (5 min)

9. Review (5 min)

三、教学重点与难点

1．教学重点

(1) Newman projection of ethane and cyclohexane.

(2) Conformers of cyclohexane (boat and chair conformer).

(3) Conformers of substituted cyclohexanes.

2.教学难点

(1) angle strain, steric strain and 1,3-diaxial interaction

(2) Conformers of cyclohexane and substituted cyclohexanes.

四、教学方法选择

1.理论课堂教学

A.多媒体教学：（简要列出本章节多媒体教学设计特点及优势）

(1) List the detailed schematic diagram  

(2) Review the major concepts and materials covering the lectures

(3) Work on problems with students together to emphasize the basic knowledge covered in the lectures

B.互动教学：（根据实际情况列出案例/实例讨论、分析讨论、分组讨论、翻转课堂等互动教学内容标题）

(1) Ask questions during the lectures

(2) Solve problems together with students

2.实验课教学

No applicable

五、更新或补充内容提要

课后总结：按照实际进度对知识点分详略进行讲解

Emphasize the key knowledge and adjust the amount of materials in each section.

六、复习思考题

1. Predict the approximate size of the C-O-C bond angle in an ether.

2. Explain why H₂O (100°C) has a higher boiling point than CH₃OH (65°C).

3.Using Newman projections, draw the most stable conformer for 3-methylpentane, viewed along the C2-C3 bond.

 4. Draw 1,2,3,4,5,6-hexachlorocyclohexane with all the chloro groups in axial position.

5. Draw the two chair conformers for cis-1-ethyl-3-methylcyclohexane, and indicate which conformer is more stable.

七、学习资源、课外自主学习参考

(可以列出供学生进一步学习、拓展本章节内容的网站、著作、期刊的名称及内容等)

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry ( 5th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 4 Isomers: the arrangement of atoms in space.

授课时间

4 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

1. 知识目标：

1. Understand the stereochemistry concept: chiral center, asymmetric center, compound optical rotation concept

2. Identify R, S configurations of chiral compound, stereoisomer, enantiomer, diastereomer, racemic- meso-compound.

3. Specifically for SP³ carbon (cis/trans isomer for cyclic saturated ring compounds), or compounds with double bond (E/Z isomer, or cis/trans isomer)

4. Optical rotation calculation, compound ee percentage

2. 授课内容（依据教学大纲）及时间分配

1. Introduction of stereochemistry（20 min）

The concept of stereochemistry, constitutional isomer/stereoisomer

2. Cis/trans isomer (20min)

The concept and model of cis/trans compounds

3. Concept of configuration/conformer (25 min)

4. Chiral and achiral compounds (20 min)

Compounds with asymmetric center, enantiomers, asymmetric center vs. stereocenter

5. How to draw enantiomers, naming enantiomers (25 min)

6. Plane-Polarized Light and compound optical rotation character, measurement, calculation formula (25 min)

7. Specific examples of chiral compounds, natural rich/drugs, highly related to the biological function, lock/key cartoon picture.(25 min)

3. 教学重点与难点

1. 教学重点

（1）the chiral property of sp3 hybridized carbon

（2）the concept of configuration and conformer

(3) the property of chiral compounds, physical/chemical property, chemical reactivity and biological function, et al are closely related to the stereochemistry of the compound  

(4) structure property determines both physical and chemical properties.

2. 教学难点

（1）naming configurations of chiral compounds

（2）compounds with two or more than two chiral centers (erythro, threo compounds)

4. 教学方法选择

1. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Pictures or cartoons to show the chiral centers, cis/trans centers

Use animal model to show configuration/conformer concept

B. 互动教学：

20 mins in class Q-A section at the end of the lecture

2. 实验教学：

Use molecular model to construct a sp3 hybrized carbon

Student group study, 4 students in one group.

Let the students to construct, name the chiral compounds, cyclic cis/trans isomers

5. 更新或补充内容提要

No updated contents, all concepts are covered in the PPT and textbook

6. 复习思考题

Textbook page 185.

Problems: 54 draw all possible stereoisomers for each of the following. Indicated if no stereoisomers are possible.

Problem 58. Are the following pairs identical, enantiomers, diastereomers, or constitutional isomers?

Problem 65. Are the following pairs identical, enantiomers, diastereomers, or constitutional isomers.

Problem 73. Which is the configuration of the asymmetric centers in the following structures?

7. 学习资源、课外自主学习参考

Designated textbook

Page 180-184 reading and knowledge expansion study, self-taught  

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 5 Alkenes: structure, Nomenclature, and introduction to reactivity. Thermodynamics and Kinetics

授课时间

4 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Nomenclature of alkene, chain alkene or cyclic alkene

2. Carbon-carbon double bond feature, bond angle, restricted rotation, cis/trans configuration, E/Z isomer, substitute priority

3. Reactions on the double bond---the electronphilic addition reaction-mechanism

4. Reduction or oxidation of double bond

2. 授课内容（依据教学大纲）及时间分配

1. Definition of double bond（15 min）

The bond character, unsaturation concept, naming et al

2. The electrophilic addition reaction (35 min)

Two step reaction mechanism, formation of carbon cation is the slow step, the second step is the fast step.

3. The concept of nucleophile and electrophile (15 min)

4. Curve arrow to indicate the electron movement (20 min)

5. Themodynamic and kinetic concept (25 min)

6. The reaction coordinate diagram (15 min)

3. 教学重点与难点

教学重点

（1）nomenclature of alkenes

（2）the electrophilic reaction mechanism

(3) thermodynamic and kinetic aspects of a reaction

(4) use arrow to draw the reaction mechanism or the electron flow.

教学难点

（1）the reaction mechanism concept

（2）use arrow to draw the reaction mechanism—step by step electron movement

4. 教学方法选择

3. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Pictures or cartoons to show the electronic addition reaction mechanism

B. 互动教学：

Be sure to use blackboard to draw the reaction mechanism, step by step.

Make sure the students understand and draw the mechanism arrows on the paper or on the blackboard

4. 实验教学：

No experimental section for this chapter

5. 更新或补充内容提要

Textbook page 231-242

An exercise in drawing curved arrows: pushing elections

6. 复习思考题

Textbook page 228.

Problems 36. What is each compound’s systematic name?

Problem 46. Do the following compounds have the E or the Z configuration?

Problem 50. By following the curved red arrow, draw the product(s) of each of the following reaction steps

Problem 56. Using curved arrows, show the mechanism of the following reactions.

7. 学习资源、课外自主学习参考

Designated textbook

Page 231-241, emphasize!  

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 6 The reactions of alkenes the stereochemistry of addition reaction  

授课时间

3 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. The stereochemistry of alkene: fully understand

2. Reaction mechanism-rate limiting step and fast step

3. E-A reaction between double bond with HX, ROH (H+ as catalyst), halides, hydroboron compound and the reaction product

4. The carbon cation formation and rearrangement

5. Stability of the stable carbon cation-the hyperconjugation concept

6. The oxidation of double bond by peroxides, ozonolysis, KMnO₄

7. Hydrogenation or reduction of double bond

8. Regioselective reaction: syn addition or anti addition

2. 授课内容（依据教学大纲）及时间分配

1. The electrophilic reaction between double bond with HX, ROH, halides(Cl₂ and Br₂) and hydroborane（25 min）

2. Stereochemistry aspect of electrophilic reaction (25 min)

3. The regiochemistry aspect of electrophilic reaction, syn/anti addition (15 min)

4. The carbon cation formation and rearrangement (20 min)

5. The oxidation reaction of double bond (10 min)

6. The reduction reaction of the double bond (15 min)

3. 教学重点与难点

教学重点

（1）the reaction of double bonds: electrophilic addition, oxidation and reductions

(2) the stereochemistry and regiochemistry aspects of the E-A reaction

.

教学难点

（1）the carbon cation stability and rearrangement

（2）the product configuration of the EA reaction

4. 教学方法选择

5. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Pictures or cartoons to show the electronic addition reaction mechanism

B. 互动教学：

Use blackboard to draw the reaction mechanism, step by step.

students are required to understand and draw the Electrophilic addition reaction mechanism

6. 实验教学：

Use molecular model to illustrate how double bond is broken, formation of carbon cation, rearrange, and the step fast step progress.

5. 更新或补充内容提要

Reading assignment: page 294

Topic one: enzymes

Topic two: receptors the carvone and the drug thalidomide

6. 复习思考题

Textbook page 300.

Problems 59. What is the major product of each of the following reactions?

Problem 61. What will be the major product, indicate the product stereochemistry

Problem 70. What reagents are needed to carry out the following synthesis?

7. 学习资源、课外自主学习参考

有机化学，尤启东 主编，

Reading hyperconjugation, carbon cation section.  

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 7 the reactions of alkynes: an introduction to multistep synthesis   

授课时间

4 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Nomenclature of alkynes

2. Reactions on the carbon/carbon triple bond

3. E-A reaction between triple bond and HX, ROH (H+ as catalyst), halides, and the reaction product

4. The regioselective aspect of the electrophilic reaction for terminal triple bond.

5. Hydrogenation reaction: to single bond or double bond-catalyst controlled

6. The oxidation reaction of the triple bond

2. 授课内容（依据教学大纲）及时间分配

1. The electrophilic reaction between triple bond with HX, ROH, halides (Cl₂ and Br₂). Triple bond is even less reactive and Hg is needed to catalyze the addition of triple bond with water（25 min）

2. The regiochemistry aspect of the electrophilic reaction (25 min)

3. The terminal proton can be removed by strong base (NaNH₂) and the acetylene acts as nucleophile (10 min)

4. Introduction of retrosynthetic analysis, synthesis problem solving practice

3. 教学重点与难点

3. 教学重点

（1）the reaction of triple bonds: electrophilic addition, oxidation and reductions

(2) the terminal alkyne: regioselective reaction and carbon nucleophile formation

(3) the synthesis problems: formation of new bonds

.

4. 教学难点

1. the triple bond electrophilic addition mechanism

2. always refer to the double bond reactions

（3）synthesis problem solving

4. 教学方法选择

7. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Pictures or cartoons to show the electronic addition reaction mechanism

B. 互动教学：

Use blackboard to draw the reaction mechanism, step by step.

students are required to understand and draw the Electrophilic addition reaction mechanism

in class practice synthesis problems

5. 更新或补充内容提要

Reading assignment: page 329. An introduction to multistep synthesis

And page 335. Summary of reactions

6. 复习思考题

Textbook page 336.

Problems 27. What is the major product obtained from the reaction of each of the following compounds with excess HCl

Problem 32. What reagents could be used to carry out the following syntheses?

Problem 45. How can the following compounds be prepared using ethyne as the starting material?

7. 学习资源、课外自主学习参考

Corresponding chapter and sections in the following books.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019级药学, 全英文班

授课章节

Chapter 8   Delocalized electrons and their effect on stability, pKa, and the products of a reaction

授课时间

6 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

Master the concept of electron delocalization

Be able to draw resonance structures

Fully understand and can apply electron delocalization effect to explain chemical stability, pKa, and product formation

2. 授课内容（依据教学大纲）及时间分配

The concept of electron delocalization, and how to draw molecule resonance (20 min)

Electron delocalization energy, resonance hybrid is more stable (20 min)

Lecture the benzene, then aromatic compounds, correlates with electron delocalization theory (30 min)

Allylic and benzylic cation, carbon cation stability is explained by electron delocalization (10 min)

Conjugated double/triple bond----electron delocalization (15 min)

Delocalized electron affects pKa value, use substituted benzoic acids, aniline as typical examples (15 min)

Delocalized electron can affect the reaction product: use conjugated diene with HX reaction, which gave 1,4 or 1,2 addition product. Also recalls the carbon cation rearrangement (10 min)

Kinetic and thermodynamic products of diene with HX reaction, reversible and irreversible reaction (10 min)

The Diels–Alder reaction, a [4+2] cycloaddition reaction (40 min)

3. 教学重点与难点

教学重点

1. the electron delocalization concept

2. Benzene and aromaticity

(3) how electron delocalization affects the stability, pKa, and reaction product formation

(4) the D-A reaction, [4+2] cycloaddition reaction

教学难点

1. Resonance contributors/ hybridization, delocalization exists in molecules which are planar, sp2 hybridized carbon directly attached to N, O, S atoms, carbon cation/carbon anion involvement

2. The deduction process of benzene molecule, the aromatic compounds further help to understand the electron delocalization concept

（3）D-A reaction, different product can be formed when there is alternative alignment of diene and dienophile, understand why only one product is provided.

4. 教学方法选择

8. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Pictures or cartoons to show the deduction of benzene structure, aromaticity and D-A reaction process

B. 互动教学：

B1. Use blackboard to draw the electron delocalization in the molecule

B2. Every four students are divided to a group, to draw the compound resonance structures/contributors

B3. in class practice the [4+2] reaction product

5. 更新或补充内容提要

Reading assignment: page 404-411.

Drawing resonance contributors

Rules for drawing resonance contributors: moving pi electrons and lone pair electrons

6. 复习思考题

Textbook page 396.

Problems 57. Which of the following have delocalized electrons.

Problem 64. Draw resonance contributors for the following species.

Problem 67. Which resonance contributor in each pair makes the greater contribution to the resonance hybrid?

Problem 73. Give the D-A reaction product for the following reaction.

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 9   Substitution reaction of alkyl halides

授课时间

4 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Master the S_N1, and S_N2 reaction, stereochemistry

2. The reactivity sequence for primary, secondary and tertiary alkyl halides

3. Be able to give the right substitution product with correct configuration

2. 授课内容（依据教学大纲）及时间分配

1. S_N2 reaction, nucleophile and electrophile, reaction transition state, configuration inversion, the bimolecular reaction, the rate of the reaction (20 min)

2. Nucleophilicity and basicity (15 min)

3. How the solvent/alkyl halide/nucleophile affect S_N2 reaction (25 min)

4. Use S_N2 reaction in organic synthesis (20 min)

5. S_N1 reaction, difference with S_N2 reaction, involvement of carbon cation formation, formation of racemic mixture. Rate of the S_N1 reaction (30 min)

6. Benzylic and allylic alkyl halide (S_N1and S_N2) (20 min)

3. 教学重点与难点

教学重点

1. S_N1and S_N2 reaction process

2. The stereochemistry of S_N1and S_N2 reaction, the halide reactant type and the reaction mechanism relation

3. Nucleophile front side approach or backside attack the electrophile.

教学难点

1. The reactant structure and the nucleophile property determines the reaction proceeds through S_N1 or S_N2 mechanism.

2. It is kind of difficult to understand the solvent effect on the substitution reaction

4. 教学方法选择

9. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Use pictures to show the reaction process and reaction diagram of S_N1 or S_N2 mechanism

B. 互动教学：

B1. Use blackboard to draw the S_N1 or S_N2 mechanism

B2. In class practice substitution reaction in organic synthesis.

5. 更新或补充内容提要

Reading assignment: page 450-452.

Topic: methylation agents used by chemists versus those used by cells

6. 复习思考题

Textbook page 453.

Problem 42. Rank the following species in order from best nucleophile to poorest nucleophile

Problems 48. Which reaction in each of the following pairs will take place more rapidly?

Problem 50. Fill in the blanks in the following chemical equations.

Problem 61. Propose a mechanism for the following reactions.

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 10  Elimination reaction of alkyl halides

授课时间

4 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Master the E1, and E2 reaction, be able to draw reaction mechanism and give the reaction product

2. The reactivity sequence for primary, secondary and tertiary alkyl halides

2. 授课内容（依据教学大纲）及时间分配

1. E2 reaction, in the presence of base, alkyl halide can eliminate halide along with the beta hydrogen, give the alkene product. The whole process is the reversible reaction of electrophilic addition (20 min)

2. The competition of S_N2 and E2, because the base acts as nucleophile (for substitution) and as base (for elimination) (15 min)

3. The E2 product follow the Z rule when there is regioselectivity, while the alkyl fluorides and the quaternary amines are the two exception (20 min)

4. How the base and leaving group (F, Cl, Br, I) affect the E2 reaction. (15min)

5. E1 reaction, monomolecular reaction (20 min)

6. The reactivity of alkyl halide, primary, secondary and tertiary alkyl halides (15 min)

7. E2 elimination from 6-membered ring, trans configuration is required, axial or equatorial bond relative position (15 min)

8. Proof of E2 elimination, the isotope effect(Deuterium) (10 min)

9. Competition between substitution and elimination: the reactant type, the reactant stereochemistry, the base, the reaction, especially temperature (20 min)

10. Organic synthesis practice, using substitution/elimination to prepare compounds

3. 教学重点与难点

5. 教学重点

4. The competition of substitution and elimination reaction, give the right product based on the reactant type, base, stereochemistry, and reaction condition.

5. Give the stereochemistry of substitution or elimination product

6. 教学难点

3. The reactant structure and the nucleophile/base property determines the reaction proceeds through substitution or elimination mechanism.

4. Complex application of substitution/elimination reaction to synthesize some simple organic compounds.

5. Elimination reactions on the six-membered ring

4. 教学方法选择

10. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Use pictures to compare substitution and elimination reaction

B. 互动教学：

B1. Use blackboard to further emphasize the substitution and elimination reaction mechanism

B2. In class practice substitution/elimination reaction in organic synthesis.

5. 更新或补充内容提要

6. 复习思考题

Textbook page 493.

Problem 35. Draw the major product obtained when each of the following alkyl halides undergoes an E2 reaction

Problems 40. Which reactant in each of the following pairs will undergo an elimination reaction more rapidly? Explain your choice

Problem 52. Draw the elimination products obtained under E2 conditions for each of the following alkyl halides.

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5^th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 11  Reactions of alcohols, ethers, epoxides, amines and thiols

授课时间

5 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Nomenclature of alcohol, ether, epoxide, amine and thiols

2. Master the reactions of alcohols, ethers, epoxides, amines and thiols

3. The substitution, dehydration and oxidation of alcohols

2. 授课内容（依据教学大纲）及时间分配

1. Alcohol nomenclature (15 min)

2. The activation then substitution of alcohol. Under acidic condition, using SOCl₂, MsCl, TsCl to convert alcohol to alkyl halide (30 min)

3. the dehydration reaction of alcohol, region/stereoselectivity of the dehydration reaction (25 min)

4. the oxidation reaction of alcohol, using different oxidant (15min)

5. epoxide nomenclature and reactions of epoxide, under basic/acidic condition (20 min)

6. The reactivity of thios, mainly as strong nucleophile (10 min)

7. The Hoffman elimination reaction, compare with alkyl fluoride elimination (10 min)

8. Overall summary of family II compounds

3. 教学重点与难点

教学重点

1. The activation of alcohol so that can be converted to alkyl halide, the substitution reaction of alcohol.

2. The dehydration of alcohol to make alkene, the reverse reaction of alkene addition

3. Reactions of epoxides under acidic or basic condition.

教学难点

1. Activation of alcohol, how and why activation is needed in order to convert alcohol to alkyl halide.

2. How the reaction condition affects the reaction product distribution.

3. The dehydration reaction of alcohol is regioselective and stereoselective

4. 教学方法选择

1. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

B. 互动教学：

B1. Use blackboard to draw thionyl chloride, tosylate activation of alcohol

B2. The dehydration reaction product formation can be shown using a molecule model

5. 更新或补充内容提要

The crown ether knowledge is covered in the reference book

Reading textbook page 544-546, summary of reactions

6. 复习思考题

Textbook page 546.

Problem 48. Draw the product of the following reactions

Problems 51. Write the appropriate reagent over each arrow.

Problem 54. Draw the major products of each of the following reactions.

Problem 76. Propose a mechanism for the following reaction.

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5^th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 12  Organometallic compound

授课时间

5 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Carbon as nucleophile when carbon atom is attached to metal

2. Use carbon nucleophile to construct carbon-carbon bond

2. 授课内容（依据教学大纲）及时间分配

1. Carbon as nucleophile agents, organolithium, Grignard reagent, Gilman reagent, transmetallation (25 min)

2. The Alkyl group of an organocuprate replaces a halogen (25 min)

3. The Suzuki and Heck reactions, palladium catalyzed coupling reaction (20 min)

4. Alkene Metathesis or olefin metathesis, Grubbs catalyst (25 min)

3. 教学重点与难点

教学重点

1. the construction of carbon-carbon bond using organocompounds.

2. the Suzuki and Heck reaction mechanism, how Pd and base are involved in the reaction process

3. the alkene metathesis, Grubbs catalyst

教学难点

1. The name reaction mechanism, proposed step by step transformation of Suzuki and Heck reaction. The reaction is a multistep reaction, not very straightforward.

2. The name reaction mechanism, proposed step by step transformation of cross metathesis reaction

4. 教学方法选择

2. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Blackboard drawing the reaction process to help understanding the transformation step by step

B. 互动教学：

B1. In class discussion for the multistep reactions

B2. Group questioning and learning small topics

5. 更新或补充内容提要

the construction of carbon-carbon bond is very important in organic synthesis, examples to illustrate complex molecule synthesis from small fragments---involvement of carbon-carbon bond formation.

Reading assignment: page 570 summary of reactions

6. 复习思考题

Textbook page. 571

Problem 23. Draw the products of each of the following reactions

Problems 28. Draw the products of each of the following reactions.

Problem 26. Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds and be prepared.

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5^th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 13  Radicals Reaction of Alkanes

授课时间

5 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Name the saturated hydrocarbon compounds

2. Master the radical mechanism for saturated hydrocarbons

3. Radical reaction mechanism three steps, radical substation and radical addition

2. 授课内容（依据教学大纲）及时间分配

1. Nomenclature of saturated hydrocarbons (15 min)

2. Radical substitution reaction, radical initiation, propagation and termination. chlorination and bromination of alkane (15 min)

3. The difference of chlorination and bromination of alkane, explain the selectivity as well as the reactivity difference (20 min)

4. Peroxide as radical reaction initiator to initiate radical addition reaction (25 min)

5. The stereochemistry of radical substitution reaction, relative stability of radical, the racemic product formation.

6. NBS is used to brominate the allylic and benzylic carbon (radical substitution reaction). (15 min)

7. Practice multistep synthesis, start from stable alkane, change to more reactive alkyl halide (25 min)

3. 教学重点与难点

教学重点

1. Radical reaction steps---initiation, propagation and termination.

2. Radical substitution reaction, stereochemistry. Peroxide as initiator

3. Radical addition reaction

4. Practice of multiple step synthesis

教学难点

1. Chlorination and bromination difference for radical substitution reaction.

2. NBS is used as bromination reagent to react with allylic/benzylic position.

3. Addition vs hydrogen removal (substitution)

4. 教学方法选择

3. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Blackboard drawing the radical reaction process

B. 互动教学：

B1. In class discussion for the radical reaction

B2. Group questioning and answering small topics

5. 更新或补充内容提要

Reading assignment: page 605. Some important things to remember;

Page 605-606. Summary of reactions

6. 复习思考题

Textbook page. 606

Problem 25. Draw the products of each of the following reactions, disregarding stereoisomers.

Problems 29. Draw the major products of each of the following reactions, disregarding stereoisomers.

Problem 36. Starting with cyclohexane, how could the following compounds be prepared?

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5^th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 16  Reactions of carboxylic acids and carboxylic derivatives

授课时间

6 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Name the carboxylic acid and derivatives

2. Master the addition-elimination reaction on the carboxylic acid derivatives

3. Reactivity sequence of carboxylic acid derivatives

2. 授课内容（依据教学大纲）及时间分配

1. Nomenclature of carboxylic acid, nitrile, acyl chloride, ester(lactone), amide (lactam) (25 min)

2. The physical property of carboxylic acid and derivatives (20 min)

3. The addition-elimination reaction mechanism, formation of tetrahedron reaction intermediate then elimination, slow then fast step. Isotope labeling to prove this proposed reaction mechanism (20 min)

4. The reactivity sequence of carboxylic acid, from most reactive to least reactive, reactive member can be transformed to less reactive member (25 min)

5. Acid catalyzed or base promoted hydrolysis of ester or amide, reaction condition matters (20 min).

6. Nitrile hydrolysis to prepare carboxylic acid, or hydrogenation to prepare primary amine. (15 min)

7. Activation of carboxylic acid to acyl chloride, to prepare ester and amide (25 min)

3. 教学重点与难点

教学重点

1. The addition-elimination mechanism for carbonyl group.

2. The reactivity of carboxylic acid derivatives, less reactive member is activated first, then being used to prepare esters or amides, mostly.

3. Practice of multiple step synthesis

教学难点

1. The nomenclature of carboxylic acid and derivatives, there are a number of type of compounds, be familiar and remember so many names.

2. The activation of carboxylic acid to acyl chloride using SOCl₂, or to anhydride by reacting with the 2^nd molecular carboxylic acid.

4. 教学方法选择

4. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Blackboard drawing the addition-elimination reaction process.

B. 互动教学：

B1. In class discussion the A-E reaction

B2. Group learning activation of the carboxylic acid

5. 更新或补充内容提要

Reading assignment: page 795-804.

How chemists activate carboxylic acids

How cells activate carboxylic acids.

Summary of reactions

6. 复习思考题

Textbook page. 804

Problem 56. Name the following compounds

Problem 58. What products would be obtained from the following reactions?

Problems 71. Which of the following reactions will not give the carbonyl product shown?

Problem 77. What are the products of the following reactions?

Problem 93. Propose a mechanism that will account for the formation of the product.

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5^th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 17. Reactions of aldehydes and ketones: more reactions of carboxylic acid derivatives

授课时间

6 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Name the aldehydes and ketones

2. Master the addition reaction on the carbonyl group of aldehyde and ketone

3. Reaction product of aldehyde/ketone with organometallic compound, hydride providing reagents, alcohol, amine, et al.

2. 授课内容（依据教学大纲）及时间分配

1. Nomenclature of aldehydes and ketons, functional group priority (20 min)

2. The physical property of aldehydes and ketons (10 min)

3. The carbonyl feature and the addition reaction mechanism of carbonyl: carbon nucleophile (Grignard reagent, organolithium, Gilman reagent, acetylene, cyano), hydride (H as nucleophile, NaBH₄, LAH, DIBAL), oxygen (H₂O, alcohol), nitrogen (primary and secondary amine), thio nucleophiles (40 min)

4. Cyclic acetal or thioacetal are protective groups used for carbonyl protection, silyl ether protection of OH group (20 min)

5. Aldehyde/ketone reacts with peroxyacid to give esters, the oxidation reaction (5 min).

6. The Wittig reaction to construct carbon-carbon double bond. (5 min)

7. α,β-unsaturated aldehyde/ketone, 1,2 or 1,4 addition reaction (15 min)

8. organic synthesis-retrosynthesis practice (25 min)

3. 教学重点与难点

教学重点

1. Nomenclature of aldehyde and ketone

2. The addition reaction of carbonyl with different nucleophiles.

3. The oxidation and reduction of carbonyl.

4. Practice of multiple step synthesis

教学难点

1. The nomenclature of aldehyde and ketone.

2. The α,β-unsaturated aldehyde/ketone, reaction regioselectivity.

3. Carbonyl and amine reaction should be carried at pH 4-5, explanation.

4. Retrosynthesis analysis for complex molecules, synthesis route design.

4. 教学方法选择

5. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Blackboard drawing the addition reaction process.

B. 互动教学：

B1. In class discussion: the addition reaction

B2. Group learning the all sorts of nucleophiles

5. 更新或补充内容提要

Reading assignment: page 865-869. Summary of reactions

6. 复习思考题

Textbook page. 869

Problem 53. Name the following compounds

Problem 54. What are the products of the following reactions?

Problems 56. Show the reagents required to form the primary alcohol in each of the following reactions.

Problem 58. Using cyclohexanone as the starting material, describe how each of the following compounds could be synthesized?

Problem 59. Propose a mechanism for the following reaction.

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5^th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 16. Reactions at the a-carbon of carbonyl compounds

授课时间

6 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. The α position of aldehyde and ketone: acidity and reactivity

2. Application of the α hydrogen acidity to proceed different reactions

2. 授课内容（依据教学大纲）及时间分配

1. α-hydrogen acidity: aldehyde/ketone, nitrile, ester (15 min)

2. keto-enol tautomerization (10 min)

3. halogenation and alkylation of the α position (10 min)

4. aldol-addition and aldol-condensation reaction, the E1cb reaction (20 min)

5. weak base (OH) or strong base (LDA) affects the reaction product (10 min).

6. formation of enamine and application of enamine for α position reaction. (10 min)

7. α,β-unsaturated aldehyde/ketone, the Michael reaction (5 min)

8. the Claisen, Dieckmann, Robinson reaction. Inter and intra molecular reaction (15 min)

9. the decarboxylation reaction of β-carbonyl compounds. (5 min)

10. application of malonic ester, acetoacetic ester in the organic synthesis (15 min)

11. organic synthesis-retrosynthesis practice (25 min)

3. 教学重点与难点

教学重点

1. α-Position acidity

2. α Position reactivity.

3. α-position carbon as nucleophile to react with other carbonyl group in ketone/aldehyde, ester, et al.

4. Practice of multiple step synthesis

教学难点

1. The α-position carbon involved reaction.

2. Application of α-position carbon to construct carbon-carbon bond.

3. Complex molecules preparation

4. 教学方法选择

6. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Blackboard drawing the retrosynthesis analysis and product formation.

B. 互动教学：

B1. In class discussion

B2. Group learning multistep synthesis

5. 更新或补充内容提要

Reading assignment: page 923-926. Summary of reactions

6. 复习思考题

Textbook page. 927

Problem 54. What is the product of the following reactions?

Problem 58. Identify A-L structure.

Problems 65. Indicate how the following compounds could be synthesized from cyclohexanone and any other reagents.

Problem 67. Indicate how each of the following compounds could be synthesized from the given starting material and any other necessary reagents

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5^th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 19. Reactions of Benzene and Substituted Benzenes

授课时间

6 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Master the electrophilic aromatic substitution of benzene

2. The directing effect of the existing group  

3. Master the nucleophilic aromatic substitution of benzene

4. Organic synthesis practice

2. 授课内容（依据教学大纲）及时间分配

1. Nomenclature of benzene and mono, di, tri-substituted benzene (15 min)

2. The electrophilic aromatic substitution reaction, two-step reaction (15 min)

3. Halogenation, sulfonation, nitration, F-C alkylation, F-C acylation of benzene (30 min)

4. The Clemmensen reaction, Wolff-Kishner reaction and application to introduce straight chains on the benzene ring (10 min)

5. Oxidation of the alkyl substitute to make benzoic acid (5 min).

6. Activating group and deactivating groups, and how the existing group affect the reactivity and directing the incoming group, the ortha/para or meta-directing group. (20 min)

7. Substitute on the benzene ring affect the pKa of phenol, aniline, benzonic acid (15 min)

8. Designing a synthesis (20 min)

9. Arene diazonium and Sandermer reaction, the application. (15 min)

10. The S_NAr reaction, for mono, di, or tri-NO₂ substitute benzenes (15 min)

11. organic synthesis-retrosynthesis practice (20 min)

3. 教学重点与难点

教学重点

1. Halogenation, sulfonation, nitration, F-C alkylation, F-C acylation of benzeneα Position reactivity. The Electrophilic aromatic substitution reaction mechanism

2. The meta, ortha/para substitute affects the reactivity.

3. S_NAr reaction

4. Practice of multiple step synthesis

教学难点

1. The directing effect of the existing group.

2. Designing a synthetic route to prepare substituted benzene.

4. 教学方法选择

7. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Blackboard drawing the retrosynthesis analysis and product formation.

B. 互动教学：

B1. In class discussion

B2. Group learning multistep synthesis

5. 更新或补充内容提要

Reading assignment: page 988-990. Summary of reactions

6. 复习思考题

Textbook page. 993

Problem 46. Draw the structure for each of the following

Problem 57. Show how the following compounds could be synthesized from benzene?

Problem 60. What are the products of the following reaction?

Problems 86. Identify A-J structures.

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5^th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 20. More About Amines

Reactions of Heterocyclic Compounds

授课时间

4 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Name hetero aromatic compounds

2. Pyrrole, thiophene, furan and pyridine, reactions of these heterocyclic compounds   

2. 授课内容（依据教学大纲）及时间分配

1. Nomenclature of hetero aromatic compounds (15 min)

2. Amines are base, and commonly used nucleophiles, can react with alkyl halide, carbonyl containing compounds (15 min)

3. The reaction of pyrrole, thiophene, furan and pyridine (30 min)

3. 教学重点与难点

教学重点

1. the electrophilic aromatic substitution reaction of hetero aromatic compounds

教学难点

This part is straight forward

4. 教学方法选择

理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

Blackboard drawing the reaction process and product formation.

B. 互动教学：

B1. In class discussion

5. 更新或补充内容提要

Reading assignment: page 1040-1042. Summary of reactions

6. 复习思考题

Textbook page. 1042

Problem 22. What are the products of the following reaction?

Problem 37. What are the major products of the following reaction?

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5^th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 22. The Organic Chemistry of Amino Acids, Peptides, and Proteins

授课时间

5 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Name and structure of the 21 commonly used amino acids

2. The physiochemical property of the amino acid

3. Preparation method of amino acid

4. Formation of peptide bond   

2. 授课内容（依据教学大纲）及时间分配

1. The common structural feature of amino acid, the side chain, the one letter, three letter abbreviation of the 21 amino acid (20 min)

2. The property of the amino acids, Zwitterion, PI calculation (20 min)

3. The HVZ reaction, the Strecker synthesis to prepare amino acid (10 min).

4. Peptide bond and method to form amide bond (15 min)

5. Protein primary, secondary, tertiary and quaternary structure, disulfide bond (15 min)

3. 教学重点与难点

教学重点

1. the side chain feature of the 21 amino acids

2. amide bond formation-review some reactions learn in the chapter of carboxylic acid and derivatives

教学难点

1. the side chain feature of the 21 amino acids

2. amide bond formation-review some reactions learn in the chapter of carboxylic acid and derivatives

4. 教学方法选择

8. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

B. 互动教学：

B1. In class discussion

B2. Group learning

5. 更新或补充内容提要

Reading assignment: page 1126. Summary of reactions

6. 复习思考题

Textbook page. 1127

Problem 52. Draw the form of aspartate that predominates at the following pH values:

Problem 70. Show how valine can be prepared by a. a Hell-Volhard-Zelinski (HVZ) reaction, b. a Strecker synthesis, c. a reductive amination reaction. d. a N-phthalimidomalonic ester synthesis. e. an acetamidomalonic ester synthesis.

7. 学习资源、课外自主学习参考

Corresponding chapter and section in the following book.

1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, Oxford University Press, 2001.

2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry  Editor：Paul M. Dewick

3. Advanced Organic Chemistry (5^th Ed), Smith, Michael B. and Jerry March

课程名称

Organic Chemistry

所属学科

药学

教材名称

Organic Chemistry  

by Paula.Y. Bruice, 7th edition

授课年级

2019药学, 全英文班

授课章节

Chapter 26. The Chemistry of the Nucleic Acids

授课时间

4 teaching hours

1. 教学目标：含知识目标、技能（能力）目标

知识目标：

1. Name and structure of the base, nucleoside, nucleotide and nucleic acid

2. RNA, DNA structural unit, property, difference  

2. 授课内容（依据教学大纲）及时间分配

1. Purine: adenine, guanine, and pyrimidine: cytosine, uracil, thymine (15 min)

2. 4 nucleosides in DNA, and 4 nucleosides in RNA, why DNA uses T other than U (20 min)

3. The mono, di, tri-phosphates, AMP, cAMP, ADP, ATP; dAMP, dADP, dATP (15 min).

4. Biosynthesis of nucleic acid (15 min)

5. Base pairing in DNA, secondary structure, double a helix (15 min)

6. Why DNA doesn’t have a 2’-OH, explanation (10 min)

7. Antiviral drugs

3. 教学重点与难点

教学重点

the 5 bases used in DNA/RNA molecule, and the construction of DNA/RNA

教学难点

1. the structure of the bases, nucleoside, nucleotide, RNA/DNA

2. Why DNA has Ts other than Us

3. Why DNA doesn’t have a 2’-OH, chemical transformation of U to T

4. 教学方法选择

9. 理论课堂教学

A. 多媒体教学：

PPT text form to introduce and lecture the contents

B. 互动教学：

B1. In class discussion