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Draw the stereoisomers that will be formed from the

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

Solution for problem 17P 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 17P

Draw the stereoisomers that will be formed from the following SN1 reactions:

a. 3-bromo-3-methylpentane and methanol

b. 3-chloro-3-methylhexane and methanol

Step-by-Step Solution:

Solution 17P

Step 1 of 5</p>

Stereochemistry of  reactions :

The nucleophile attacks the carbon atom on the opposite side of the leaving group and the carbon atom turns inside out as the reaction goes just like an inside out umbrella. If the carbon atom under attack is stereogenic centre the product will be inversion of configuration. In  reactions the intermediate is carbocation. As carbocation is planar the nucleophile attacks the two faces of the planar cation and gives the product exactly  mixture of -isomer and -isomer. It is said to be racemic mixture.

Step 2 of 5</p>

(a)

3-Bromo-3-methylpentane undergoes  reaction to form tertiary carbocation intermediate.

Step 3 of 5</p>

Methanol acts as a nucleophile. Methanol can attack on both front and back side of tertiary carbocation intermediate to form a racemic mixture.

Step 4 of 5

Chapter 9, Problem 17P is Solved
Step 5 of 5

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

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