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Propose a mechanism for the hydrolysis of

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 20P Chapter 21

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 20P

Problem 20P

Propose a mechanism for the hydrolysis of N,N-dimethylacetamide

(a) under basic conditions.

(b) under acidic conditions.

Step-by-Step Solution:

Solution 20P

Step 1

(a) The mechanism for the hydrolysis of N, N- dimethyl acetamide under basic conditions is as follows:

This mechanism takes place in three steps. 1) Addition of the nucleophile (2) Elimination of the leaving group and (3) Proton transfer

Step 1: Addition of nucleophile:

Base attacks on the carbonyl carbon to form a tetrahedral intermediate.

Step 2 of 3

Chapter 21, Problem 20P is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Propose a mechanism for the hydrolysis of