有机合成课件 第2章 基础有机合成

----Preparation of Alkene----
1. Dehydrohalogenation of Alkyl Halide 2. Dehydration of Alcohols 3. Dehalogenationof Vicinal Dihalides 4. Reduction of Alkynes
Example:
CH3CH2Cl Li
CH3CH2
CuI
Li
CH3CH2 CH3CH2
CuLi
Ethylchloride Ethyllithium
Lithium
dialkylcoper
CH3(CH2)5CH2Br
n-Heptyl bromide
CH3CH2CH2(CH2)5CH3
n-Nonane
h
5
R - X + M g R - M g X H 2 O R - H
Example:
C H 3C H 2C H C H 3M gC H 3C H 2C H C H 3 H 2OC H 3C H 2C H C H 3
B r
M g B r
H
sec-B utyl brom ide
sec-B utylm agnesium br hom ide
1 -B u te n e
h
8
3. Dehalogenation of vicinal dihalides
Example:
C H 3 C H B r C H B r C H 3 Z nC H 3 H CC H C H 3
2 ,3 -D ib r o m o b u ta n e
2 -B u te n e
3 o > 2 o > 1 o
Examples:
C H 3 C H 2 C H 2 C H 2 O H a c idC H 3 C H 2 H C C H 2 C H 3 H C C H C H 3
n - B u t y l a lc o h o l
1 - B u t e n e
2 - B u t e n e
n-B utane
3
b) Reduction by metal and acid. R - X + Z n + H + R - H + Z n 2 + + X -
Example:
C H 3C H 2C H C H 3
B r
sec-Butyl brom ide
Zn+H +
C H 3C H 2C H C H 3 H
Examples:
C H 3 C H 2 C H 2 C H 2 C lK O H (a lc o h o l)C H 3 C H 2 H CC H 2
n -B u ty l c h lo r id e
1 -B u te n e
C H 3 C H 2 C H C l C H 3 K O H ( a l c o h o l )C H 3 H C C H C H 3 C H 3 C H 2 H C C H 2
h
9
4. Reduction of alkynes
h
10
----Preparation of Alcohol----
1. Oxymercuration-Demercuration 2. Hydroboration-Oxidation 3. GrignardSynthesis 4. Hydrolysis of Alkyl Halides 5. Hydroxylation of Alkenes
n-Butane
h
4
3. Coupling of alkyl halides with organometalic compounds.
来自百度文库
R-X
M ay be
1o， 2o， 3o
R-Li
Alkyllithium
R2-CuLi
Lithiumdial kylcopper
R'-X
Shouldbe1o
R-R'
C h ie f p r o d u c t
C H 3 C H 2 C H O H C H 3a c idC H 3 H CC H C H 3C H 3 C H 2 H CC H 2
s e c -B u ty l a lc o h o l
2 -B u te n e C h ie f p r o d u c t
h
2
----Preparation of Alkane----
1. Hydrogenation of alkene
C n H 2n H 2+ P t,P d ,N i C n H 2n + 2
A lk en e
A lk en e
2.Reduction of alkyl halides
a) Hydrolysis of Grignard reagent.
h
6
----Preparation of Alkene----
1. Dehydrohalogenation of alkyl halide
C C +K O Halcohol C C +K X+H 2O
HX
Ease of dehydrohalogenayion of alkyl halides 3o>2o>1o
h
11
----Preparation of Alcohol----
1. Oxymercuration-demercurataion
2. Hydroboration-Oxidation
h
12
3. Grignard synthesis 4.Hydrolysis of alkyl halides Examples:
Chapter 2 Basic of Organic Synthesis
h
1
----Preparation of Alkane----
1.Hydrogenation of Alkenes 2. Reduction of Alkyl Halides 3. Coupling of Alkyl Halides with Organometalic Compounds
s e c - B u t y l c h l o r i d e
2 - B u t e n e8 0 % 1 - B u t e n e2 0 %
h
7
2. Dehydration of alcohols
a c id
C C H O H
E a s e o f
C C+ H 2 O d e h y d r o g e n a tio n o fa lc o h o ls