Solved: The Wohl degradation, an alternative to the Ruff degradation, is nearly the
Chapter 0, Problem 23-37(choose chapter or problem)
The Wohl degradation, an alternative to the Ruff degradation, is nearly the reverse of the KilianiFischer 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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