Chapter 23: Question 23.6 (page 1214)

a) Draw D-allose, the C3 epimer of glucose.

b) Draw D-talose, the C2 epimer of D-galactose.

c) Draw D-idose, the C3 epimer of D-talose. Now compare your answers with Figure 23-3.

d) Draw the C4 “epimer” of D-xylose. Notice that this “epimer” is actually an L-series sugar, and we have seen its enantiomer. Give the correct name for this L-series sugar.

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(a.)

(b.)

(c.)

(d.)

Step by step solution

01

Epimers

Epimers are the compounds which are stereoisomers and differ at only one stereogenic center, like, the placing of the OH group is different from the other.For example, D-glucose and D-galactose are epimers having only one chiral center with different configuration.

02

The structure of D-allose, D-talose, 2-idose, and their comparison

a. Epimers are stereoisomers which differ in configuration at any one stereogenic or chiral center. C3 epimer of glucose means that configuration differs at carbon-3 of glucose which gives rise to different stereoisomer that is, D-allose. Position of hydroxyl group in glucose at carbon-3 is on the left, whereas position of hydroxyl group at carbon-3 of D-allose is on the right.

The structure of D-allose

b. Similarly, D-talose is C2 epimer of D-galactose and differs in configuration at carbon-2. Position of hydroxyl group in D-galactose is on the right at carbon-2 whereas in D-talose, it is on the left. D-idose is C3 epimer of D-talose and differs in configuration at carbon-3.

The structure of D-talose

c. Position of hydroxyl group is on the left at carbon-3 in D-talose. whereas it is on the right in D-idose.

The structure of D-idose

03

The C4 epimer of D-xylose

d. C4 epimer of D-xylose is L-arabinose. Change in configuration at carbon-4 of D-xylose with respect to hydroxyl group changes the sugar series from “D” to “L” as the change occurs at bottom chiral center which as per convention, leads to formation of enantiomer. The D/L system names molecules by relating them to glyceraldehyde molecule.

The C4 epimer of D-xylose

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Most popular questions from this chapter

The relative configurations of the stereoisomers of tartaric acid were established by the following synthesis:

(1) D-(+)-glyceraldehydediastereomers A and B (separated)

(2) Hydrolysis of A and B using aqueous Ba(OH)2 gave C and D, respectively.

(3) HNO3 oxidation of C and D gave (-)-tartaric acid and meso-tartaric acid, respectively.

(a) You know the absolute configuration of D-(+)-glyceraldehyde, Use Fischer projections to show the absolute configurations of products A, B, C, and D.

(b) Show the absolute configurations of the three stereoisomers of tartaric acid: (+)-tartaric acid, (-)-tartaric acid, and meso-tartaric acid.

Treatment of either anomer of fructose with excess ethanol in the presence of a trace of HCI gives a mixture of the α and β anomers of ethyl-D-fructofuranoside. Draw the starting materials, reagents, and products for this reaction. Circle the aglycone in each product.

(a) Which of the D-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?

(b) Which of the D-aldotetroses will give optically active aldaric acids on oxidation withHNO3 ?

(c) Sugar X is known to be a D-aldohexose. On oxidation with HNO3 , X gives an optically inactive aldaric acid. When X is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine the structure of X.

(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an optically active aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form optically active products?

(e) Show what products results if the aldopentose formed from degradation of X is further degraded to an aldotetrose. DoesHNO3 oxidize this aldotetrose to an optically active aldaric acid?

Ruff degradation of D-arabinose gives D-erythrose. The Kiliani-Fischer synthesis converts D-erythrose to a mixture of D-arabinose and D-ribose. Draw out these reactions and give the structure of D-ribose.

The carbonyl group in D-galactose may be isomerized from C1 to C2 by brief treatment with dilute base (by enediol rearrangement, Section 23-7). The product is the C4 epimer of fructose. Draw the furanose structure of the product.

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