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Chapter 28: Question 28.53 (page 1149)

What two aldohexoses yield d-arabinose upon Wohl degradation?

Short Answer

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Answer

Step by step solution

01

Wohl degradation

Wohl degradation is an important reaction in carbohydrate chemistry. This reaction shortens the carbon chain in a stepwise manner by cleaving the bond of the aldose chain.

02

From D-glucose

D-glucose is treated with NH2OH,AC2O gives a cyanohydrin further react with NaOCH3 form D-arabinose.

Formation of D-arabinose from D-glucose

03

From D-mannose

D-mannose is treated with NH2OH,Ac2O,AcONa,AcOHforms a product with on further reaction with NaOCH3form D-arabinose.

Formation of D-arabinose from D-mannose

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Most popular questions from this chapter

Deduce the structure of the disaccharide maltose from the following data.

[1]Hydrolysis yields D-glucose exclusively.

[2] Isomaltose is cleaved with -αglycosidase enzymes.

[3] Isomaltose is a reducing sugar.

[4]Methylation with excess CH3I,Ag2Oand then hydrolysis withH3O+ forms two products:

(Both anomers are present.)

Draw a stepwise mechanism for the following hydrolysis.

Draw a stepwise mechanism for the following reaction.

Convert each ball-and-stick model to a Fischer projection.

(a.)

(b.)

The most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the αorβ anomers of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.
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