Organic Chemistry, Books a la Carte Edition (8th Edition)
Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Chapter 20, Problem 67P
Interpretation Introduction

Interpretation:

The mechanism for the elimination step in the Wohl degradation is to be drawn.

Concept Introduction:

In Wohl degradation, the first step is aldose carbonyl group is converted to the oxime.  Then oxime is dehydrated by an acetic anhydride to give the nitrile (a cyanohydrin).  The formation of cyanohydrin is reversible in nature.  It undergoes a basic hydrolysis to give aldose with one less carbon with a loss of HCN molecule.

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Organic Chemistry, Books a la Carte Edition (8th Edition)

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