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Chapter 20: Q59P (page 985)

The aldaric acid of D-glucose forms two five-membered-ring lactones. Draw their structures.

Short Answer

Expert verified

Aldaric acid of D-glucose forms two five-membered ring lactones. One has R configuration and other is of S configuration.

Step by step solution

01

Structure of D-glucose and aldaric acid of D-glucose

The structure of D-glucose is given below:

Hydroxyl group at the last carbon atom and the aldehyde group at first carbon atom is oxidized to form aldaric acid.

The structure of aldaric acid of D-glucose is shown below:

02

Step 2: Formation of two 5-membered lactones

Aldaric acid forms two 5-membered lactones which are shown below:

Two 5-membered lactones are formed by rotating the aldaric acids in 180o . So each of the lactone will have difference in their configuration, i.e. one lactone has R configuration at the second last carbon atom while the other has S configuration.

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Most popular questions from this chapter

An unknown disaccharide gives a positive Tollens’ test. A glycosidase hydrolyzes it to d-galactose and d-mannose. When the disaccharide is treated with methyl iodide and Ag2O and then hydrolyzed with dilute HCl, the products are 2,3,4,6-tetra-O-methylgalactose and 2,3,4-tri-O-methylmannose. Proposea structure for the disaccharide.

a. What other monosaccharide is reduced only to the alditol obtained from the reduction of 1. D-talose? 2. D-glucose? 3. D-galactose?

b. What monosaccharide is reduced to two alditols, one of which is the alditol obtained from the reduction of 1. D-talose? 2. D-allose?

The specific rotation of α-d-galactose is 150.7 and that of b-d-galactose is 52.8. When an aqueous mixture that was initially 70% α-d-galactose and 30% β-d-galactose reaches equilibrium, the specific rotation is 80.2. What is the percentage of α-d-galactose and β-d galactose at equilibrium?

What is the main structural difference between

a. amylose and cellulose?

b. amylose and amylopectin?

c. amylopectin and glycogen?

d. cellulose and chitin?

Indicate whether each of the following structures is D-glyceraldehyde or L-glyceraldehyde, assuming that the horizontal bonds point toward you and the vertical bonds point away from you (Section 4.7):

a.

b.

c.
See all solutions

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