+ZnBr ОН H20 CH;CH Н + CH,Cн OCH3 CH3CH,CHCH OCH3 CH3CH,CHCH' OCH3 ZnBr ČH3 CH3 B-hydroxy ester organozinc reagent Describe how each of the following compounds can be prepared, using a Reformatsky reaction: ОН ОН ОН С. .C. a. CH;CH,CH,ĊHCH, OCH3 b. CH;CH,CHCH CH3CH,CH=Ç Но, d. CH3CH,CCH2 OCH3 с. HO, CH2CH3 CH3 CH2CH3

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.11: Nucleophilic Addition Of Phosphorus Ylides: The Wittig Reaction
Problem 17P: -Carotene, a yellow food-coloring agent and dietary source of vitamin A can be prepared by a double...
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The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of
an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur.
The organozinc reagent is prepared by treating an a-bromo ester with zinc.

Describe how each of the following compounds can be prepared, using a Reformatsky reaction:

+ZnBr
ОН
H20
CH;CH
Н + CH,Cн
OCH3
CH3CH,CHCH
OCH3
CH3CH,CHCH'
OCH3
ZnBr
ČH3
CH3
B-hydroxy ester
organozinc reagent
Describe how each of the following compounds can be prepared, using a Reformatsky reaction:
ОН
ОН
ОН
С.
.C.
a. CH;CH,CH,ĊHCH,
OCH3
b. CH;CH,CHCH
CH3CH,CH=Ç
Но,
d. CH3CH,CCH2
OCH3
с.
HO,
CH2CH3
CH3
CH2CH3
Transcribed Image Text:+ZnBr ОН H20 CH;CH Н + CH,Cн OCH3 CH3CH,CHCH OCH3 CH3CH,CHCH' OCH3 ZnBr ČH3 CH3 B-hydroxy ester organozinc reagent Describe how each of the following compounds can be prepared, using a Reformatsky reaction: ОН ОН ОН С. .C. a. CH;CH,CH,ĊHCH, OCH3 b. CH;CH,CHCH CH3CH,CH=Ç Но, d. CH3CH,CCH2 OCH3 с. HO, CH2CH3 CH3 CH2CH3
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