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Arrange the following alkyl bromides in order of

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

Solution for problem 5P 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 5P

Arrange the following alkyl bromides in order of decreasing reactivity in an SN2 reac­tion:

l-bromo-2-methylbutane, l-bromo-3-methylbutane, 2-bromo-2-methylbutane, and 1-bromopcntane.

Step-by-Step Solution:

Solution 5P

Step 1 of 3</p>

The mechanism of an  reaction involves a backside attack by the nucleophile on the substrate and is thus accompanied by a crowding at the reaction site in transition state.

More crowding would mean more hindrance and less  reactivity. Thus, among all the least reactivity towards  reaction is shown by 2-bromo-2-methylbutane.

Step 2 of 3</p>

In reaction, the nucleophile attacks from the back of the leaving group. So, the more the branching at  carbon or the carbons adjacent to it, less will be the probability of back side attack resulting in decrease in  products. Thus, 1-bromo-2-methylbutane is the least reactive among the other three compounds.

Step 3 of 3

Chapter 9, Problem 5P is Solved
Textbook: Organic Chemistry
Edition: 7
Author: Paula Yurkanis Bruice
ISBN: 9781269406772

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