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Chapter 28: Question 28.59 (page 1149)

Draw a stepwise mechanism for the following hydrolysis.

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01

Reaction mechanism

Reaction mechanism constitutes a sequential procedure that details the transformation of reactants into products. Numerous kinds of reactions are present in organic chemistry, and one among them is the hydrolysis reaction.

02

Hydrolysis of carbohydrates

Monosaccharides are created by the acid hydrolysis of carbohydrates like disaccharides and polysaccharides.

In the hydrolysis procedure of carbohydrates, the long molecules (polymers) are reduced into smaller units (monomers).

03

Stepwise mechanism for the given hydrolysis

The first step involves the oxygen protonation of the glycosidic linkage. The protonated oxygen gets subjected to the cleavage of the glycosidic linkage forming an acetal. This acetal undergoes protonation, and the methanol molecule gets eliminated.

This forms a carbocation. The water molecule strikes the carbocation. This is followed by the deprotonation to form a glucose molecule.

The mechanism can be given as:

The stepwise mechanism for the hydrolysis reaction

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

(a.)

(b.)

Classify each compound as a reducing or nonreducing sugar.

(a.)

(b.)

(c.)

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.)

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.
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