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For each pair, predict the stronger nucleophile in the

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

Solution for problem 16P Chapter 6

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 16P

For each pair, predict the stronger nucleophile in the reaction (using an alcohol as the solvent). Explain your prediction.

Step-by-Step Solution:

Solution 16P

Step 1

The  reaction relies on the rear-side attack of a strong nucleophile on a sterically unhindered electrophile containing a good leaving group.

(a)

The pair of compounds are  and.

Note that  is a secondary amine, and is less hindered than the other compound (which is a tertiary amine). There is less steric hindrance around the secondary amine, and so it will be the stronger nucleophile; it can more easily attack the electrophile.

Therefore,  will be the stronger nucleophile.

Step 2 of 7

Chapter 6, Problem 16P is Solved
Step 3 of 7

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

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