Chapter 24.6, Problem 36CC

Interpretation Introduction

Interpretation:

The name and structure of two aldohexoses that undergoes Wohl degradation to yield D-ribose should be determined.

Concept introduction:

The Wohl degradation: D-glucose is reaction with hydroxylamine and sodium methoxide which yields oxime then resultant oxime is reaction with acetic anhydride in acetic acid with sodium acetate which afforded pentaacetyl glycononitrile. In this reaction step the oxime is converted into the nitrile with simultaneous conversion of all the alcohol groups to acetate groups. Finally, sodium methoxide in methanol is added to the reaction which yields the final degradation compound.