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. +ZnBr ОН CH;CH CH,CH,CHCH .C OCH3 CH;CH,CHCH .C OCH3 OCH3 Но CH3CH CH3 ZnBr organozinc reagent ČH3 B-hydroxy ester Describe how each of the following compounds can be prepared, using a Reformatsky reaction: ОН ОН ОН C. ОН .C. a. CH;CH,CH,CHCH b. CH3CH,CHCH CH,CH3 OCH3 с. СН-СH-CH—С ОН d. CH3CH2CCH OCH3 CH3 CH,CH3

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. +ZnBr ОН CH;CH CH,CH,CHCH .C OCH3 CH;CH,CHCH .C OCH3 OCH3 Но CH3CH CH3 ZnBr organozinc reagent ČH3 B-hydroxy ester Describe how each of the following compounds can be prepared, using a Reformatsky reaction: ОН ОН ОН C. ОН .C. a. CH;CH,CH,CHCH b. CH3CH,CHCH CH,CH3 OCH3 с. СН-СH-CH—С ОН d. CH3CH2CCH OCH3 CH3 CH,CH3

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Question

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.
+ZnBr
ОН
CH;CH
CH,CH,CHCH
.C
OCH3
CH;CH,CHCH
.C
OCH3
OCH3
Но
CH3CH
CH3
ZnBr
organozinc reagent
ČH3
B-hydroxy ester
Describe how each of the following compounds can be prepared, using a Reformatsky reaction:
ОН
ОН
ОН
C.
ОН
.C.
a. CH;CH,CH,CHCH
b. CH3CH,CHCH
CH,CH3
OCH3
с. СН-СH-CH—С
ОН
d. CH3CH2CCH
OCH3
CH3
CH,CH3

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