ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Chapter 16, Problem 42DSP
Interpretation Introduction

Interpretation:

The ketone formed in the pinacol re-arrangement of the vicinal diol 1 is to be identified.

Concept Introduction:

During pinacol re-arrangement, a diol is converted to a ketone.

The reaction begins by protonation of one of the hydroxyl groups.

In the next step, the water molecule departs, and an alkyl group from the adjacent carbon atom migrates to its position.

A new carbocation is created, where the hydroxyl group is attached to the carbon bearing the positive charge.

The unshared electrons pair on this hydroxyl group stabilizes the carbocation.

The final step is the formation of a carbonyl group and abstraction of a proton from the oxygen atom.

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