Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 16, Problem 47DSP
Interpretation Introduction

Interpretation:

The product formed in the given reaction is to be identified.

Concept Introduction:

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

The loss of hydroxyl group produces initial carbocation. The initial carbocation results in the most stable carbocation.

In the next step, the water molecule departs, and a methylene group that is anti 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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