北京大学视频公开课

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This course of Organic Chemistry in English was first given in the fall semester of 2008 at the College of Chemistry in Peking University. This is an undergraduate student class for chemistry majors from the college of Chemistry and Yuan Pei College at Peking University. It is also available as an optional course to the undergraduate students from other colleges and departments. Around 40 students register for the class every year, including a number of international students from the college of chemistry.

Name: Organic Chemistry I & II (English Version)
Instructor: Prof. Yuguo Ma, Prof. Dahui Zhao
Credit: 3 + 2
Semester: Fall (I) Spring (II)
Requirment: Native English Speaker or English as First Foreign Language

Course Goals:
At the end of the course each student should be able to:
1. gain knowledge of the history of organic chemistry and nomenclatures used in organic chemistry;
2. master the basic concepts, theories, reactions, and methodologies;
3. explain the relationship between structure and physical and chemical properties and how to make predictions concerning these properties;
4. propose reasonable mechanism for organic reactions and to make predictions on the outcome of new reactions;
5. design synthetic route for organic compounds and think creatively about synthesis;
6. appreciate the important role of organic chemistry in life, both biological and economical.

Course Content:
1. Introduction of Organic Chemistry (1h)
2. Structure and Bonding (2h)
3. Polar Covalent Bonds: Acids and Bases (2h)
4. Alkanes and Cycloalkanes (4h)
5. Alkenes and Alkynes (6h)
6. Stereochemistry (3h)
7. Alkyl Halides (5h)
8. Structure Determinataion (5h)
9. Benzene and Aromatic Compounds (6h)
10. Alcohols, Phenols, Ethers, and Epoxides (6h)
11. Aldehydes and Ketones (6h)
12. Carboxylic Acids and Derivatives (9h)
13. Orbitals and Organic Chemistry: Pericyclic Reactions (4h)
14. Amines and Heterocycles (6h)
15. Biomolecules: Carbohydrates (3h)
16. Amino Acids, Peptides, and Proteins (2h)
17. Lipids and Nucleic Acids (1h)
18. Synthetic Polymers (1h)

Gradings:
1. Homework, quiz, discussion, essays: 40%
2. Final Exam: 60%

Prof. Yuguo Ma

Prof. Yuguo Ma obtained his B.Sc. degree with honor in 1994 and a Master degree in 1997 from College of Chemistry at Peking University, under supervision of Prof. Qi-Feng Zhou. He continued his graduate study in the Department of Chemistry at University of Illinois at Urbana-Champaign with Prof. Steven C. Zimmerman, and obtained his Ph.D. in Organic Chemistry in December 2002. From January 2003 to August 2005, he was a postdoc research associate with Prof. Geoffrey W. Coates in the Department of Chemistry and Chemical Biology of Cornell University.

In September 2005, he returned to Peking University as an Associate Professor at College of Chemistry, and was promoted to full Professor in 2011. He is currently serving as deputy director of Key Lab of Polymer Chemistry and Physics of Ministry of Education. In 2008, he was selected to be in “Program of Excellent Talents for New Century” by the Ministry of Education of China.

Prof. Ma’s research interest includes: Supramolecular Chemistry; Molecular Recognition and Self-Assembly; Organic Functional Materials based on Dendrimers; Organometallic Catalysis; etc.

The classes he is teaching at PKU include: (for undergraduate students) Organic Chemistry (in English); Experimental Organic Chemistry; (for graduate students) Synthetic Polymer Chemistry; Special Topics in Polymer Science, etc. He won “Yao Ming Kang De” award for teaching from College of Chemistry of PKU in 2010.

马玉国博士，教授，博士生导师，1972年2月生。1994年和1997年7月于北京大学化学学院分别获得学士（北京地区高校优秀毕业生）和硕士学位，师从周其凤院士。2002年12月在美国依利诺伊大学化学系获得有机化学博士学位，师从Steven C. Zimmerman教授。2003年1月至2005年8月在美国康奈尔大学化学与化学生物学系Geoffrey W. Coates教授的实验室做博士后。

2005年9月起任北京大学化学学院高分子系副教授，2007年5月遴选为博士生导师，2011年8月晋升为教授。2008年入选“教育部新世纪优秀人才支持计划”。2007年起任高分子化学与物理教育部重点实验室副主任。

课题组的主要研究兴趣及领域包括：高分子的超分子化学；分子识别及自组装；Dendrimer为基础的光电材料；烯烃的立体选择及立体规整聚合反应等。回国后已在以上研究方向发表学术论文40篇（其中影响因子大于4.0的有32篇；以通讯和共同通讯作者发表35篇）。根据“SCI论文在线检索”所发论文已被引用1037次，其中他引801次，单篇被引用最高次数为104。已经申请中国专利六项，已经获得授权三项。受邀撰写英文专著一章、中文专著两章。

在北京大学承担的本科生课程有：《有机化学》（英文），《有机化学实验》；研究生课程有：《高分子合成化学》，《高分子科学专题与展望》等。2010年获北京大学化学学院 “药明康德”奖教金。

Prof. Dahui Zhao

Prof. Dahui Zhao received her B.Sc. degree with honor in 1997 at Peking University. She conducted her graduate study in the Department of Chemistry at University of Illinois at Urbana-Champaign with Prof. Jeffrey S. Moore. After obtaining her Ph.D. in Organic Chemistry in December 2003, she then performed her post-doctoral research with Prof. Timothy M. Swager in the Department of Chemistry at Massachusetts Institute of Technology (MIT).

In March 2006, she started her independent career at the College of Chemistry in Peking University as an associate professor. Prof. Zhao’s research interests includes: supramolecuar chemistry of conjugated systems; designs and syntheses of new organic/polymer materials with optical & electronic functions. She was selected to the “Nova” program of the Beijing Municipal Science and Technology Commission in 2007, and the “Program of Excellent Talents for New Century” by the Ministry of Education of China in 2011.

She is now teaching the classes of Organic Chemistry (in English, for undergraduate students) and the Chemistry of Today. She won the first prize in the teaching competition of young professors of Peking University in 2011.

赵达慧博士，副教授，博士生导师。1997年毕业于北京大学化学学院，获得学士学位（北京地区高等学校优秀毕业生）。1999年8月进入美国依利诺伊大学化学系攻读有机化学博士学位（导师：Jeffrey S. Moore 教授）。2003年12月获得博士学位后，进入美国麻省理工学院Timothy M. Swager教授（美国科学院院士）课题组进行博士后研究。留学期间曾获得R. C. Fuson Memorial Travel Award与Vanderveer Voorhees Original Research Proposal Award等多项奖励和荣誉。

2006年3月起任北京大学化学学院副教授和课题组长，同年遴选为博士生导师。研究方向为：具有多层次、多尺度有序超分子结构的有机/高分子光电功能材料的研究。已发表论文20余篇，他引总数>600次，单篇最高引用>200次。2007年入选北京市科技新星计划，2008年获霍英东教育基金会高等院校青年教师基金优选资助课题，2011年获日本化学会授予的Distinguished Lectureship Award，2012年入选教育部“新世纪优秀人才支持计划”，并获国家自然科学基金委优秀青年科学基金。

承担北京大学本科生课程：《有机化学》（英文）、《今日化学》。2011年获得北京大学青年教师教学基本功大赛一等奖、北京大学“绿叶生物医药奖教金”。

Name: Organic Chemistry I & II (English Version)
Instructor: Prof. Yuguo Ma, Prof. Dahui Zhao
Credit: 3 + 2
Semester: Fall (I) + Spring (II)
Requirement: English as First Foreign Language or Native English Speaker

Course Goals:

At the end of the course each student should be able to:

gain knowledge of the history of organic chemistry and nomenclatures used in organic chemistry;
master the basic concepts, theories, reactions, and methodologies;
explain the relationship between structure and physical and chemical properties and how to make predictions concerning these properties;
propose reasonable mechanism for organic reactions and to make predictions on the outcome of new reactions;
design synthetic route for organic compounds and think creatively about synthesis;
appreciate the important role of organic chemistry in life, both biological and economical.

Course Content:

1. Introduction of Organic Chemistry (1h)           chapter 0

2. Structure and Bonding (2h)           chapter 0 chapter 9
(1) Atomic Structure
(2) Development of Chemical Bonding   Theory (Important Points)
(3) The Nature of Chemical Bonds: Valence Bond Theory and Hybrid Orbitals (Difficult Points)
(4) The Nature of Chemical Bonds: Molecular Orbital Theory (Important Points)

3. Polar Covalent Bonds: Acids and Bases (2h)        chapter 0
(1) Electronegative and Dipole Moment
(2) Formal Charges and Resonance (Difficult Points)
(3) Acids and Bases: The Bronsted-Lowry Definition and The Lewis Definition (Important Points)
(4) Noncovalent Interaction (Introductory)

4. Alkanes and Cycloalkanes (4h)    chapter 1   chapter 2 chapter 3
(1) Functional Groups (Important Points)
(2) Alkanes and Alkane Isomers
(3) Naming Alkanes and Cycloalkanes
(4) Cis-Trans Isomerism in Cycloalkanes (Important Points)
(5) Properties of Alkanes and Stability of Cycloalkanes: Ring Strain (Difficult Points)
(6) Conformations of Alkanes and Cycloalkanes (Important Points)

5. Alkenes and Alkynes (6h)     chapter 8   chapter 9 chapter 10
(1) Degree of Unsaturation (Important Points)
(2) Overview of Organic Reactions and Reaction Mechanism (Important Points)
(3) Electrophilic Addition Reaction of Alkenes (Important Points)
(4) The Hammond Postulate (Difficult Points)
(5) Carbocation Rearrangements (Difficult Points)
(6) Preparation and Reactions of Alkynes

6. Stereochemistry (3h) (Important Points)     chapter 4
(1) The Reason for Handness in Molecules: Chirality (Difficult Points)
(2) Optical Activity and Pasteur’s Discovery of Enantiomers
(3) Sequence Rules for Specifying Configuration (Important Points)
(4) Diastereomers and Meso Compounds (Important Points)
(5) Racemic Mixtures and the Resolution of Enantiomers
(6) Stereochemistry of Reactions (Difficult Points)

7. Alkyl Halides (5h)       chapter 5 chapter 6   chapter 7
(1) Naming and Structure of Alkyl Halides
(2) Preparation and Stability of Alkyl Halides
(3) Naming Alkanes and Cycloalkanes
(4) Reaction of Alkyl Halides: SN1, SN2, E1, E1cB and E2 (Important + Difficult Points)
(5) Organometallic Coupling Reactions (Introductory)

8. Structure Determinataion (5h)      chapter 11 chapter12
(1) Mass Spectrometry and Infrared Spectroscopy (Introductory)
(2) Nuclear Magnetic Resonance Spectroscopy (Important Points)
(3) Ultraviolet Spectroscopy and Conjugated Compounds

9. Benzene and Aromatic Compounds (6h) (Important Points)    chapter 15

(1) Structure and Stability of Benzene
(2) Aromaticity and the Hückel 4n+2 Rule (Difficult Points)
(3) Aromatic Heterocycles and Polycyclic Aromatic Compounds
(4) Electrophilic Aromatic Substitution (Important Points)
(5) Nucleophilic Aromatic Substitution (Important Points)

10. Alcohols, Phenols, Ethers, and Epoxides (6h)      chapter 13 chapter 14 chapter 22
(1) Naming and Properties of Alcohols, Phenols, Ethers, and Epoxides
(2) Preparation and Reaction of Alcohols, Phenols, Ethers, and Epoxides (Important Points)

11. Aldehydes and Ketones (6h)     chapter 16
(1) Naming and Preparation of Aldehydes and Ketones
(2) Nucleophilic Addition Reaction of Aldehydes and Ketones (Important Points)
(3) Conjugated Nucleophilic Addition to α,β-Unsaturated Aldehydes and Ketones (Difficult Points)

12. Carboxylic Acids and Derivatives (9h)     chapter 17 chapter 18 chapter 19
(1) Naming and Structure of Nitriles, Carboxylic Acids and Derivatives
(2) Properties and Preparation of Caboxylic Acids and derivatives (Important Points)
(3) Chemistry of Nitriles
(4) Nucleophilic Acyl Substitution Reactions (Important Points)
(5) Carbonyl Alpha-Substitutions and Carbonyl Condensation Reactions (Important Points)

13. Orbitals and Organic Chemistry: Pericyclic Reactions (4h) (Important Points)     chapter 9   chapter 20
(1) Electrocyclic Reactions
(2) Cycloaddition Reactions
(3) Sigmatropic Rearrangements (Difficult Points)

14. Amines and Heterocycles (6h)              chapter 21      chapter 23
(1) Naming and Basicity of Amines
(2) Synthesis and Reaction of Amines (Important Points)
(3) Heterocycles (Important Points)

15. Biomolecules: Carbohydrates (3h)                           chapter 24

16. Amino Acids, Peptides, and Proteins (2h)                 chapter 25

17. Lipids and Nucleic Acids (1h)                      chapter 25

18. Synthetic Polymers (1h) (Introductory)        chapter 8

Reference & Materials:

Principles of Chemical Nomenclature: A Guide to IUPAC Recommendations G. J. Leigh, H. A. Favre, W. V. Metanomski, Blackwell Science Ltd. 1998.
Introduction to Stereochemistry, K. Mislow, Benjamin: New York, 1962.
Enantiomers, Racemates and Resolutions, J. Jacques, A. Collet, S. H. Wilen; Wiley: New York, 1981.
Stereochemistry of Organic Compounds, E. L. Eliel, S. H. Wilen; Wiley: New York, 1994.
Reflections of Symmetry, E. Heibronner, J. D. Dunitz; VCH: New York, 1993.
Stereochemistry of Carbon Compounds, E. L. Eliel; McGraw-Hill: New York, 1962.
Grossman, R. B. “Van’t Hoff, LeBel, and the Development of Stereochemistry: A Reassessment.” J. Chem. Ed. 1989, 66, 30-36.
Mislow, K.; Siegel, J. “Stereoisomerism and Local Chirality”, J. Am. Chem. Soc. 1984, 106, 3319.
S. Krishnamurthy and Herbert C. Brown “Selective Reductions. 27. Reaction of Alkyl Halides with Representative Complex Metal Hydrides and Metal Hydrides. Comparison of Various Hydride Reducing Agents.” J. Org. Chem. 1980, 45, 849-856.
Hoye, T. R.; Hanson, P. R.; Vyvyan, J. R. “A Practical Guide to First-Order Multiplet Analysis in lH NMR Spectroscopy” J. Org. Chem. 1994, 59, 4096-4103.
Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. “NMR chemical Shifts of Common Laboratory Solvents as Trace Impurities” J. Org. Chem. 1997, 62, 7512-7515.
Ito, Y.; Hirao, T.; Saegusa, T. “Synthesis of α,β-unsaturated carbonyl compounds by palladium(II)-catalyzed dehydrosilylation of silyl enol ethers” J. Org. Chem., 1978, 43, 1011-1013.
Canham, S. M.; France, D. J.; Overman, L. E. “Total Synthesis of (+)-Sieboldine A” J. Am. Chem. Soc. 2010, 132, 7876–7877.
Murata, Y.; Yamashita, D.; Kitahara, K.; Minasako, Y.; Nakazaki, A.; Kobayashi, S. ”Synthetic Study of (-)-Norzoanthamine: Construction of the ABC Ring Moiety” Angew. Chem. Int. Ed. 2009, 48, 1400 –1403.
Yamashita, D.; Murata, Y.; Hikage, N.; Takao, K.-i.; Nakazaki, A.; Kobayashi, S. ”Total Synthesis of (-)-Norzoanthamine” Angew. Chem. Int. Ed. 2009, 48, 1404 –1406.

	Organic Chemistry--Structure and Function, 5th Ed., 2007, K. Peter C. Vollhardt and Neil E. Schore, Freeman and Company, ISBN 0-7167-9949-9. .
	Organic Chemistry, International Student Edition, 7th Ed., 2008, John McMurry, Brooks/Cole Publishing Company, ISBN 0-495-11628-9.