Draw the substitution products that will be formed from

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

Problem 7P 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 7P

Draw the substitution products that will be formed from the following SN2 reactions:

a. cis-1-bromo-4-methylcyclohexane and hydroxide ion

b. trans-1-iodo-4-ethylcyclohexane and methoxide ion

c. cis-1-chloro-3-methylcyclobutane and ethoxide ion

Step-by-Step Solution:

Solution 7P

Step 1 of 3</p>

(a)

The configuration of product of  reactions involves an inversion of configuration. In these reactions the incoming nucleophile attack the * orbital of the  bond. This means that the nucleophile should attack the leaving group directly from behind, leading to inversion of configuration. If the leaving group is axial, then the incoming nucleophile will end up at equatorial.

Step 2 of 3</p>

(b)

Methoxide ion reacts with -1-iodo-4-ethylcyclohexane by  mechanism to form -1-ethyl-4-methoxycyclohexane.

Step 3 of 3

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

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