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Chapter 28: Question 28.53 (page 1149)

What two aldohexoses yield d-arabinose upon Wohl degradation?

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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

Draw the products formed when D-arabinose is treated with each reagent. (a) Ag2O,NH4OH; (b)Br2,H2O ; (c)HNO3,H2O ,

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 Haworth projection for each compound using the structures in Figures 28.4 and 28.5.

A 2-ketohexose is reduced with NaBH4 in CH3OH to form a mixture of D-galactitol and D-talitol. What is the structure of the 2-ketohexose?

For D-arabinose:

  1. Draw its enantiomer.
  2. Draw an epimer at C3.
  3. Draw a diastereomer that is not an epimer.
  4. Draw a constitutional isomer that still contains a carbonyl group.
See all solutions

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