The Wohl degradation, an alternative to the Ruff degradation, is nearly the reverse of the Kiliani-Fischer synthesis.

Question:

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
Fantastic news! We've Found the answer you've been seeking!

Step by Step Answer:

Related Book For  book-img-for-question

Organic Chemistry

ISBN: 978-0321768414

8th edition

Authors: L. G. Wade Jr.

Question Posted: