Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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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 (RMgX) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.

    Essential Organic Chemistry, Global Edition, Chapter 12.5, Problem 14P

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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
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