文档介绍：By Junru Wang
Organic chemistry
室
西北农林科技大学理学院
Email: wangjr07@
袁茂森
417
,
416
张继文
87092187(O)
双语教学课件
基地班有机化学
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王俊儒
Organic Chemistry
By Junru Wang
Organic chemistry
西北农林科技大学理学院
Email: wangjr07@
Section M
Section M
Alcohols, Phenols and Thiols
Main content
M1 Preparation of alcohols
Functional group transformation:
C-C bond formation
M2 Preparation of phenols
Incorporation
Functional group transformations
M3 Properties of alcohols and phenols
Main content
M4 Reactions of alcohols
Acid-base reactions ; Elimination
Synthesis of alkyl halides; Synthesis of
mesylate; and tosylates; Oxidation
M5 Reactions of phenols
Acid-base reactions
Functional group transformation
Electrophilic substitution
Oxidation
Claisen rearrangement
M6 Chemistry of thiols
reactivity and reactions
M1 preparation of alcohols
Functional group transformation:
Functional groups such as alkyl
halides, carboxylic acids, esters,
alkenes, aldehydes, ketones, and
ethers can be transformed into
alcohols.
H
CHCH (CH(CH )) HH H
3 2 5 (CH(CH2))5CHCH3
NaOHNaOH
CC BrBr
CHCH
CHCH3 3
O
C CH2OH
OCH2CH3
1) LiAlH4
+ CH3CH2OH
2) H2O
M1 preparation of alcohols
C-C bond formation
Alcohols can be formed from epoxides,
aldehydes, ketones, esters, and acid
chlorides as a consequence of C-C bond
formation with Grignard or
organolithium reagents
CHO CH2OH
CH3OH
4 + 4CH3OH + NaBH4 4 + NaOCH3 + B(OCH3)3
96%
CH3 CH3
O H
乙醚 H2O OH
4 + LiAlH4 4 + LiOH + Al(OH)3
90%
O
R
C O + Al OCH(CH3)2 (RCHO)3Al + H3
R 3
R H O
3 RCHOH
Meerwein- Poundorf 反应 R
O OH
C
C + CH3
OCH2CH3 2CH MgBr H3O
3 CH
ether 3
Grignard and Ester
Grignard attacks the carbonyl.
Alkoxide ion leaves! ? !
H3C CH3
RMgBr CO R C O MgBr
CH3O
OCH3
CH3 CH3
R C O MgBr R C + MgBrOCH3
O
OCH
3 Ketone intermediate