1. Welcome to Reactions and Mechanisms in Organic Synthesis!

2. Introduction 主讲教师：马梦林 办公室：化学实验中心315室 2B-2007室 电 话： 87721078
电 话： ：

3. Textbook： Guidebook to Organic Synthesis
(3rd Edition)
有机合成指南
Raymond K Mackie , David M Smith, R Alan Aitken
世界图书出版公司 (1999)

4. Reference Book: Modern Methods of organic synthesis (Fourth Edition)
William Carruthers and Lain coldham
Cambridge University Press (2004)
当代有机合成方法（当代有机化学译丛）
华东理工出版社（2006）
高等有机化学—反应和机理（BERNARD）
Bernard
华东化工学院出版社（2005）

5. 无期中考试，期末成绩70%，课程设计20%，课堂练习10%。
教学安排及成绩评定
无期中考试，期末成绩70%，课程设计20%，课堂练习10%。

6. Chapter 1 Introduction
Accomplishments of organic synthesis in the twentieth century
Main factors of organic synthesis

7. 1.Total synthesis in the nineteenth century

8. 1902 Nobel Prize Winner. 1.1. The Hermann Emil Fischer
“for his work on sugar and purine syntheses .”

9. 2. Total Synthesis in the Twentieth Century 2. 1
2. Total Synthesis in the Twentieth Century The Pre-World War II Era

10. Accomplishments of organic synthesis in the twentieth century
R. B. Woodward
2.2. The Woodward Era
Woodward
1965 Nobel Prize Winner.
“for his outstanding achievements in the art of organic synthesis.”
quinine (1944), patulin (1950), cholesterol胆固醇 and cortisone (1951),lanosterol (1954), lysergic acid (1954),strychnine (1954), reserpine (1958),
chlorophyll a 叶绿素(1960),colchicine (1965), cephalosporin C (1966), Prostaglandin F2a (1973),vitamin B12 (with A. Eschenmoser) (1973),erythromycin A (1981).
人工合成维生素B12、胆固醇、叶绿素等复杂有机物

11. Selected syntheses by the Woodward Group (1944 - 1981).
Ref: Angew. Chem. Int. Ed. 2000, 39, 44 – 122.

12. 威尔金森(Cerffrey Wilkinson，1921—) pioneering work, performed independently, on the chemistry of the organometallic, so called sandwich compounds"
霍夫曼 (Roald Hoffmann，1937—) "for their theories, developed independently, concerning the course of chemical reactions"

13. 2.3. The Corey Era
Corey
…Corey has thus been awarded with the Prize for three intimately connected contributions, which form a whole. Through retrosynthetic analysis and introduction of new synthetic reactions, he has succeeded in preparing biologically important natural products, previously thought impossible to achieve. Corey’s contributions have turned the art of synthesis into a science…
Nobel Lectures: Chemistry , World Scientific, New Jersey, 1992, pp

16. 3.Selected Examples of Total Syntheses
Haemin (1929)
Penicillin (1957)
Chlorophyll a (1960)

17. Main factors of organic synthesis
Formation of Molecular Frame
Functionalization
Stereochemistry of Target Molecule
Vitamin B12

18. Chapter 2 Functional group chemistry: the basics
Topics:
Selectivity of organic reactions
Functionalization (Introduction of functional group)
Interconversion of functional groups

19. 2.1 Selectivity of organic reactions
2.1.1 Chemoselectivity
2.1.2 Regioselectivity and regiospecificity
2.1.3 Stereoselectivity and stereospecificity

20. 2.2 Functionalization of alkanes
Inert to electrophilic and nucleophilic reagents
Reactive in radical reactions, particularly halogenation

21. 2.3 Functionalization of alkenes

22. 2.4 Functionalization of alkynes

23. 2.5 Functionalization of aromatic hydrocarbons
2.5.1 Substitution at a ring position

24. 2.5.2 Reaction in the side chain
Radical substitution
Halogenation
Benzylic oxidation
See section and 9.2.3
Autoxidation

25. 2.6 Functionalization of substituted benzene derivatives
Substituent
Orientation of electrophilic substitution
Rate of substitution relative to that of benzene
Alkyl or aryl
o, p
Faster
-OH, -OR
-NR2, -NHR, -NR2
Halogen
Similar or slower
C=O m
Slower
-C≡N
-NO2
-SO3H
-CF3

26. 2.7 Functionalization of simple heterocyclic compounds
Please read them yourselves after school!

27. 2.8 Interconversion of functional groups
2.8.1 Transformation of the hydroxyl group
2.8.2 Transformation of the amino group
2.8.3 Transformation of halogeno compounds
2.8.4 Transformation of nitro and cyano compounds
2.8.5 Transformation of aldehydes and ketones
2.8.6 Transformation of acids and acid derivatives

28. 2.8.1 Transformation of the hydroxyl group

29. 2.8.2 Transformation of the amino group

30. 2.8.3 Transformation of halogeno compounds

31. 2.8.4 Transformation of nitro and cyano compounds

32. 2.8.5 Transformation
of aldehydes and ketones

33. 2.8.6 Transformation
of acids and acid
derivatives

34. Summary
Functionalization and interconversion of functional group both play important parts in synthetic procedure.
Selectivity (both regio- and stereo-) are often crucial importance in synthetic sequence.
Functionalization of Alkanes, alkenes and alkynes are summarized.
Functionalization of arenes are summarized.
Functional group interconversions of alcohols and phenols, amines and diazonium salts, halogeno and nitro compounds, aldehydes and ketones, and carboxylic acids and their derivatives, are summarized.