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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

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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

Draw the mechanism for the formation of 尾-lactose from a 伪- D-galactose and 尾- D-glucose in dil HCl.

Identify A, B, C, and D in the preceding problem if D is oxidized to an optically inactive aldaric acid; if A,B, and C are oxidized to optically active aldaric acids; and if interchanging the aldehyde and alcohol groups of A leads to a different sugar.

All the glucose units in dextran have six-membered rings. When a sample of dextran is treated with methyl iodide and AgO and the product is hydrolyzed

under acidic conditions, the final products are 2,3,4,6-tetra-O-methyl-d-glucose, 2,4,6-tri-O-methyl-d-glucose, 2,3,4-tri-O-methyl-d-glucose, and 2,4-di-O-methyl-d-glucose. Draw a short segment of dextran.

What sugar is the C-3 epimer of D-fructose?

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?
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