The Wohl degradation, an alternative to the Ruff degradation, is nearly the reverse ofthe Kiliani–Fischer synthesis. The aldose carbonyl group is converted to the oxime,which is dehydrated by acetic anhydride to the nitrile (a cyanohydrin). Cyanohydrinformation is reversible, and a basic hydrolysis allows the cyanohydrin to loseHCN. Using the following sequence of reagents, give equations for the individualreactions in the Wohl degradation of d-arabinose to d-erythrose. Mechanisms arenot required.(1) hydroxylamine hydrochloride (2) acetic anhydride (3) -OH, H2O

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
Problem 37MP
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The Wohl degradation, an alternative to the Ruff degradation, is nearly the reverse of
the Kiliani–Fischer synthesis. The aldose carbonyl group is converted to the oxime,
which is dehydrated by acetic anhydride to the nitrile (a cyanohydrin). Cyanohydrin
formation is reversible, and a basic hydrolysis allows the cyanohydrin to lose
HCN. Using the following sequence of reagents, give equations for the individual
reactions in the Wohl degradation of d-arabinose to d-erythrose. Mechanisms are
not required.
(1) hydroxylamine hydrochloride (2) acetic anhydride (3) -OH, H2O

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