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a. Propose a mechanism for the following reaction.b.

Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice ISBN: 9781269406772 80

Solution for problem 64P 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 64P

a. Propose a mechanism for the following reaction.

b. Explain why two products are formed.

c. Explain why methanol substitutes for only one of the bromines.

Step-by-Step Solution:

Solution 64P

Step 1 of 5</p>

(a)

Mechanism for the formation of product 1:

This reaction follows  mechanism. The -2,3-dibromochroman loses bromide ion to form oxonium ion. It can rearrange to form a more stable carbocation.

Step 2 of 5</p>

Methanol attacks at carbocation to form another oxonium ion derivative. Methanol abstracts a proton from oxonium ion derivative to form -3-bromo-2-methoxychroman.

Step 3 of 5</p>

Mechanism for the formation of product 2:

This reaction follows  mechanism. Methanol attacks at carbon of  bond to form -3-bromo-2-methoxychroman.

Step 4 of 5

Chapter 9, Problem 64P is Solved
Step 5 of 5

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

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