Propose a mechanism for the following reaction: | Ch 9 - 61P

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

Problem 61P 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 61P

Propose a mechanism for the following reaction:

Step-by-Step Solution:

Solution 61P

Step 1 of 4</p>

The mechanism is shown as follows:

Heterolytic cleavage of carbon and halogen gives a stable carbocation.

Step 2 of 4</p>

Even though the rearrangement step transforms a stable tertiary carbocation into a less stable secondary cation, relief of strain in expansion forms a four five membered ring makes the alkyl migration favorable. Five membered rings are more stable than four membered rings due to less strain.

Step 3 of 4

Chapter 9, Problem 61P is Solved
Step 4 of 4

Textbook: Organic Chemistry
Edition: 7
Author: Paula Yurkanis Bruice
ISBN: 9781269406772

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