ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
2nd Edition
ISBN: 9780393664034
Author: KARTY
Publisher: NORTON
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Chapter 11, Problem 11.26P
Interpretation Introduction

Interpretation:

It is to be explained which of the given alkenes E-I will produce 2-chloro-3-methyl-2-phenylbutane as a major product when treated with HCl.

Concept introduction:

Given alkenes undergo an electrophilic addition reaction via carbocation rearrangement. Electrophilic addition of a Bronstead acid across a carbon-carbon double bond is susceptible to carbocation rearrangement. A carbocation rearrangement transforms the less stable carbocation into a more stable carbocation to attend greater stability via 1, 2-hydride shift or 1, 2-methyl shift. Electrophilic addition reaction proceeds through a carbocation intermediate.

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