Chapter 24, Problem 24.51AP

Interpretation Introduction

Interpretation:

The structure of missing compounds present in Wohl degradation reaction is to be stated. The curved-arrow mechanism for conversion of B to C and C to arabinose in the Wohl degradation reaction is to be shown.

Concept Introduction:

Wohl degradation is the reaction to convert aldose into other aldose with one carbon less. It is a chain contraction reaction of aldoses. The oxime of aldose is formed by reacting it with hydroxylamine and sodium methoxide. Then oxime will react with acetic anhydride in acetic acid and sodium acetate toform nitrile derivative. In the last step, the reaction with sodium methoxide in methanol results in removal of all acetate group and nitrile group toform aldose with one carbon lesser and sodium cyanide as by product.