ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.)
4th Edition
ISBN: 9781119761068
Author: Klein
Publisher: WILEY
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Textbook Question
Chapter 5.4, Problem 5.20P
Propose a mechanism for each of the following reactions:
Expert Solution & Answer
Interpretation Introduction
Interpretation:
Mechanism for the given transformation has to be proposed.
Explanation of Solution
Given reaction is,
Mechanism:
Looking into the reaction it is found that the nucleophile is a strong one namely hydroxide and the reactant has all the three important criteria to undergo
First step is the attack of nucleophile on the carbon atom that bears that chlorine atom which is a leaving group resulting in formation of Meisenheimer complex.
The formed Meisenheimer complex has the following resonance structures.
Second step is the expelling of the leaving group to give the product.
As the given condition is basic, deprotonation takes place.
Under acidic condition the formed ion is protonated to give the product. This is the reason for using acid in order to complete the reaction.
Complete mechanism can be given as shown below,
Mechanism for the given transformation is proposed.
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Students have asked these similar questions
Part I.
Draw reaction mechanism for the transformations of benzophenone to benzopinacol to benzopinaco lone and answer the ff:
Pinacol (2,3-dimethyl, 1-3-butanediol) on treatment w/ acid gives a mixture of pina colone
and
(3,3-dimethyl-2-butanone) 2,3-dimethyl-1,3-butadiene. Give reasonable mechanism
the formation of the products
For
Show the mechanism for these reactions
Draw the stepwise mechanism
Chapter 5 Solutions
ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.)
Ch. 5.1 - Prob. 5.2PCh. 5.1 - Prob. 5.3PCh. 5.1 - Prob. 5.4PCh. 5.1 - Prob. 5.5PCh. 5.1 - Prob. 5.6PCh. 5.1 - Prob. 5.7PCh. 5.2 - Propose a mechanism for each of the following...Ch. 5.2 - Propose a mechanism for each of the following...Ch. 5.2 - Propose a mechanism for each of the following...Ch. 5.3 - Prob. 5.13P
Ch. 5.3 - Prob. 5.14PCh. 5.3 - Prob. 5.15PCh. 5.3 - Prob. 5.16PCh. 5.3 - Prob. 5.17PCh. 5.3 - Prob. 5.18PCh. 5.4 - Propose a mechanism for each of the following...Ch. 5.4 - Propose a mechanism for each of the following...Ch. 5.4 - Propose a mechanism for each of the following...Ch. 5.4 - Propose a mechanism for each of the following...
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