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Chapter 28: Question 28.17 (page 1124)

What glycosides are formed when each monosaccharide is treated with CH3CH2OH, HCl:

(a) β-D-Mannose; (b)α-D-glucose ; (c) β-D-fructose ?

Short Answer

Expert verified

Answer

(a.)and

(b.)and

(c.)and

Step by step solution

01

Glycosides

‘Glycosides’ are the acetals in organic chemistry having an alkoxy (OR) group attached to the anomeric carbon (C1). These are assigned by αandβ labelsand are generated when a monosaccharide is treated with alcohol and HCl.

02

Reaction of β-D-mannose and  α-D-glucose with CH3CH2OH and HCl.

a. When β-D-mannose is treated with CH3CH2OH(ethanol) and HCl, it results in the formation of two glycosides shown below:

β-D-mannoseon treatment with ethanol and HCl

b. When α-D-glucose is treated with (ethanol) and HCl, it results in the formation of two glycosides shown below:

α-D-glucoseon treatment with ethanol and HCl

03

When β-D-fructose is treated with  CH3CH2OH and HCl.

c. When β-D-fructose is treated withCH3CH2OH(ethanol) and HCl, it results in the formation of two glycosides shown below:

β-D-fructose on treatment with ethanol and HCl

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Most popular questions from this chapter

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.)

Draw the structures of the nucleosides formed from each of the following components: (a) ribose + uracil; (b) 2-deoxyribose + guanine.

How would you convert d-glucose into each compound? More than one step is required.

(a.)

(b.)

(c.)

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 both pyranose anomers of each aldohexose using a three-dimensional representation with a chair pyranose. Label each anomers as αandβ.

(a.)

(b.)
See all solutions

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