ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Chapter 25, Problem 27P
Interpretation Introduction

Interpretation:

A mechanism is to be proposed for the given transformation which was carried out as a part of a multistep synthesis of digitoxigenin.

Concept Introduction:

Hydroxyl group is not a good leaving group.

In the presence of an acid, the hydroxyl group gets protonated and is converted to a good leaving group.

A carbocation is formed when the leaving group departs. Resonance of the positive charge stabilizes the carbocation.

Addition of water to the carbocation results in further reaction and deprotonation.

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