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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

Treating chitin with H2O,-OH hydrolyzes its amide linkages, forming a compound called chitosan. What is the structure of chitosan? Chitosan has been used in shampoos, fibers for sutures, and wound dressings.

Draw a Fischer projection of the monosaccharide from which each of the following glycosides was prepared.

Draw the products formed when 伪-D-glucoseis treated with each reagent.

a.CH3I,Ag2O

b.CH3OH,HCl

c. Ac2O, pyridine

d. The product in (a), thenH3O+

e. The product in (b), then Ac2O, pyridine

f. The product in (d), then C6H5CH2Cl,Ag2O

Draw a stepwise mechanism for the following reaction.

D-Arabinose can exist in both pyranose and furanose forms.

  1. Draw the 伪and尾anomers of D-arabinofuranose.
  2. Draw the 伪and尾 anomers of D-arabinopyranose.
See all solutions

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