Two substitution products result from the reaction of

Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice

Problem 22P Chapter 9

Organic Chemistry | 7th Edition

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Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice

Organic Chemistry | 7th Edition

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Problem 22P

Two substitution products result from the reaction of 3-chloro-3-methyl-1-butene with sodium acetate (CH3COO-Na+) in acetic acid under conditions that favor an SN1 reaction. Identify the products.

Step-by-Step Solution:

Solution 22P

Step 1 of 3</p>

3-Chloro-3-methyl-1-butene undergoes  reaction to form more stable allylic carbocation. The formed allylic carbocation can be stabilized by its resonance. Its resonance contributors are as shown below:

Step 2 of 3</p>

Acetate ion acts as a nucleophile. It can react with allylic carbocation intermediate (I) to form 2-methylbut-3-en-2-yl acetate.

Step 3 of 3

Chapter 9, Problem 22P is Solved
Textbook: Organic Chemistry
Edition: 7
Author: Paula Yurkanis Bruice
ISBN: 9781269406772

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