Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 12.5, Problem 14P
Interpretation Introduction
Interpretation:
The compound which does not undergo nucleophilic addition reaction with Grignard reagent has to be identified.
Concept introduction:
The Grignard reaction:
Alkyl, vinyl, or aryl-magnesium halides (
Grignard reagent is reaction with carbonyl compound such as
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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 ofan 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:
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
Which of the following could act as a nucleophile?
A) HCl
B) CH3NH2
C) BF3
D) CH3Br
Chapter 12 Solutions
Essential Organic Chemistry, Global Edition
Ch. 12.1 - Prob. 1PCh. 12.1 - Name the following compounds:Ch. 12.1 - Prob. 3PCh. 12.1 - Prob. 4PCh. 12.2 - Prob. 5PCh. 12.4 - Draw the structure for each of the following: a....Ch. 12.4 - Prob. 7PCh. 12.5 - What products are formed when the following...Ch. 12.5 - Prob. 9PCh. 12.5 - Prob. 10P
Ch. 12.5 - Prob. 12PCh. 12.5 - Write the mechanism for the reaction of acetyl...Ch. 12.5 - Prob. 14PCh. 12.6 - Prob. 16PCh. 12.7 - Prob. 17PCh. 12.7 - Prob. 18PCh. 12.7 - Prob. 19PCh. 12.8 - Prob. 20PCh. 12.8 - Prob. 21PCh. 12.8 - Prob. 22PCh. 12.9 - Which of the following are a. hemiacetals? b....Ch. 12.9 - Prob. 24PCh. 12.9 - Prob. 25PCh. 12.10 - Prob. 26PCh. 12.11 - Prob. 27PCh. 12 - Draw the structure for each of the following: a....Ch. 12 - Prob. 29PCh. 12 - List the following compounds in order from most...Ch. 12 - Show the reagents required to form the primary...Ch. 12 - Fill in the boxes:Ch. 12 - Indicate how the following compounds could be...Ch. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - Prob. 38PCh. 12 - Prob. 39PCh. 12 - Show two ways the following compound could be...Ch. 12 - Prob. 41PCh. 12 - Prob. 42PCh. 12 - Prob. 43PCh. 12 - Prob. 44PCh. 12 - Prob. 45PCh. 12 - Prob. 46PCh. 12 - Prob. 47PCh. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - Prob. 50PCh. 12 - Prob. 51PCh. 12 - Indicate how the following compounds could be...Ch. 12 - Prob. 53P
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