Organic Chemistry Study Guide and Solutions
Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 25, Problem 25.26AP
Interpretation Introduction

Interpretation:

The effect of addition of Lewis acid BF3 before the reduction of S-ethyl thiobenzoate (A) is to be explained.

Concept introduction:

The lithium aluminum hydride reduces the thioacetate to thiol similar to ester reduction. If the reduction of thioacetate carried out by addition of Lewis acid BF3 it gives cyclohexyl ethyl sulfide due to formation of tetrahedral intermediate having oxygen-boron bond.

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