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Chapter 28: Question 28.33 (page 1141)

Drawthe products of each reaction.

(a.)

(b.)

Short Answer

Expert verified

Answer

(a.)

Reaction a.

(b.)Reaction b.

Step by step solution

01

Reactions of carbohydrates

Both alpha and beta forms of the D-glucose react with amines under mildly acidic conditions at the anomeric carbon and form the mixture of alpha and beta N-glycosides.

02

Reaction a.

The reactant monosaccharide is α-D-glucopyranose. On reaction with amines under mildly acidic conditions, anomeric carbon reacts with it and forms the mixture of methyl substituted α-N-glucoside and β-N-glycoside.

Product formation in reaction a.

03

Reaction b.

The reactant monosaccharide is β-D-glucopyranose. On reaction with amines under mildly acidic conditions, anomeric carbon reacts with it and forms the mixture of methyl-substituted α-N-glycoside and β-N-glycoside.

Product formation in reaction b.

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Most popular questions from this chapter

(a) Draw the more stable chair form of fucose, an essential monosaccharide needed in the diet and a component of carbohydrates on mammalian and plant cell surfaces. (b) Classify fucose as a D- or L-monosaccharide. (c) What two structural features are unusual in fucose?

Draw a stepwise mechanism for the conversion of β-D-glucose to both anomers of N-ethyl glucopyranoside, the equation written in Reaction [1].

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.)

What products are formed when each compound is subjected to a Kiliani–Fischer synthesis?

(a.)

(b.)

As we have seen in Chapter 28, monosaccharides can be drawn in a variety of ways, and in truth, often a mixture of cyclic compounds is present in a solution. Identify each monosaccharide, including its proper D, L designation, draw in a less-than-typical fashion.

(a.)

(b.)

(c.)

(d.)
See all solutions

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