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Chapter 28: Question 28.18 (page 1125)

Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

The mechanism of the above reaction is followed by resonance and nucleophilic attack of H2O to form anomers.

Step by step solution

01

Glycoside

Glycoside is the molecule formed from monosaccharide, which undergoes condensation with a hydroxyl group and eliminates water.Glycosides have hemiacetal and hydroxyl groups, which on hydrolysis gives two anomers.

02

Formation of carbocation

Glycoside is hydrolyzed and forms an intermediate by the loss of H2O , which on resonance gives carbocation.

03

Formation of anomers

Carbocation was attacked by H2O on both sides (above and below). The carbocation forms an intermediate that undergoes nucleophilic attack to form 伪and尾anomers, as shown below:

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Most popular questions from this chapter

Which d-aldopentoses are reduced to optically inactive alditols using NaBH4,CH3OH?

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

(a.)

(b.)

(c.)

Drawthe structure of:

(a) a polysaccharide formed by joining d-mannose units in 1鈫�4-尾-glycosidic linkages;

(b) a polysaccharide formed by joining d-glucose units in 1鈫�6-伪-glycosidic linkages.

The polysaccharide in (b) is dextran, a component of dental plaque.

Consider the tetrasaccharide stachyose drawn below. Stachyose is found in white jasmine, soybeans, and lentils. Because humans cannot digest it, its consumption causes flatulence.

a. Label all glycoside bonds.

c. What products are formed when stachyose is hydrolyzed with H3O+?

d. Is stachyose a reducing sugar?

e. What product is formed when stachyose is treated with excess CH3I, Ag2O?

f. What products are formed when the product in (e) is treated with H3O+?

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

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