ORGANIC CHEMISTRY-W/STUD.SOLN.MAN.
ORGANIC CHEMISTRY-W/STUD.SOLN.MAN.
10th Edition
ISBN: 9781260001099
Author: Carey
Publisher: MCG
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Chapter 6.8, Problem 12P
Interpretation Introduction

Interpretation:

It is to be explained that the carbocation intermediate in the hydrolysis of 2-bromo-3-methylbutane rearranges by a hydride shift rather than a methyl shift.

Concept introduction:

The stability order of carbocation is methyl < primary < secondary < tertiary.

The carbocation can be stabilized by rearrangement due to shift of hydride or methyl group of adjacent carbon.

The selection of hydride or methyl group shift depends on the stability of carbocation formed.

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