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Chapter 20: Q67P (page 985)

Draw the mechanism for the dehydration step in the Wohl degradation

Short Answer

Expert verified

In Wohl degradation, the aldose carbonyl group gets converted to oxime in the first step. The oxime undergoes dehydration in the presence of acetic anhydride to generate a cyanohydrin.

It undergoes basic hydrolysis to produce aldose with one less carbon.

Step by step solution

01

Wohl degradation 

In Wohl degradation, the aldose carbonyl group gets converted to oxime in the first step. The oxime undergoes dehydration in the presence of acetic anhydride to generate a cyanohydrin.

It undergoes basic hydrolysis to produce aldose with one less carbon.

02

The mechanism for the dehydration step in Wohl degradation

In the last step of the mechanism, sodium methoxide in methanol is added to the compound with the nitrile group. This leads to the removal of the acetal group by hydrolyzing them.

The removal of the nitrile group happens by the loss of the HCN molecule. This leads to the formation of an aldose with one less carbon than the initial aldose.

Mechanism for the dehydration step in Wohl degradation

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Identify A, B, C, and D in the preceding problem if D is oxidized to an optically inactive aldaric acid; if A,B, and C are oxidized to optically active aldaric acids; and if interchanging the aldehyde and alcohol groups of A leads to a different sugar.

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