Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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The Wohl degradation is a series of reactions that shorten an aldose chain by one carbon, it is almost the exact opposite of the Kiliani-Fischer synthesis. In this reaction the aldose
aldehyde carbonyl group is converted into a nitrile. The resulting cyanohydrin loses HCN under basic conditions.
Conversion of the aldehyde to a nitrile is accomplished by treatment of the aldose with hydroxylamine to form an oxime. Dehydration of the oxime with acetic anhydride yields the
cyanohydrin.
Draw curved arrows to show the movement of electrons in this step of the mechanism. Where "R" is used, it represents the rest of the sugar chain.
Arrow-pushing Instructions
H2Ñ-OH
C-H
H-
HO-
HO-
но
H2N-OH
H-
Но
H.
H-
OH
HO-
OH
HO-
ČH2OH
ČH2OH
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Transcribed Image Text:The Wohl degradation is a series of reactions that shorten an aldose chain by one carbon, it is almost the exact opposite of the Kiliani-Fischer synthesis. In this reaction the aldose aldehyde carbonyl group is converted into a nitrile. The resulting cyanohydrin loses HCN under basic conditions. Conversion of the aldehyde to a nitrile is accomplished by treatment of the aldose with hydroxylamine to form an oxime. Dehydration of the oxime with acetic anhydride yields the cyanohydrin. Draw curved arrows to show the movement of electrons in this step of the mechanism. Where "R" is used, it represents the rest of the sugar chain. Arrow-pushing Instructions H2Ñ-OH C-H H- HO- HO- но H2N-OH H- Но H. H- OH HO- OH HO- ČH2OH ČH2OH
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