Draw and name the enantiomers of the sugars shown in Figure 23-2. Give the relative configuration (D or L) and the sign of the rotation in each case.

Short Answer

Expert verified

The enantiomers of glucose are D+glucoseand L()glucose.

The enantiomers of arabinose are D()arabinoseand L()arabinose.

The enantiomers of erythrose are D()erythroseand L(+)erythrose.

The enantiomers of glyceraldehyde are D(+)glyceraldehydeand L()glyceraldehyde.

Step by step solution

01

Enantiomers

Molecules having exact mirror images of itself and has non- super imposable mirror image is known as a chiral molecule. Enantiomers or optical isomers are two mirror images of a chiral molecule.

02

D or L configuration

If a compound rotates plane polarised light to the right, then it is said to be dextrorotatory D. This is indicated in the name of the compound by the prefix sign +. But if a compound rotates plane polarised light to the left, then it is said to be laevorotatory L. This is indicated in the name of the compound by the prefix sign That is, it can be said that DandL refers to the absolute configuration around the asymmetric carbon atom while (+) and (-) refers to the direction of rotation of the plane polarised light.

03

Placement of OH group for D and L series of sugars in Fischer projection

For D-series, OH group of the bottom asymmetric carbon is present on the right side in the Fischer projection while for L-series, OH group of the bottom asymmetric carbon is present on the left side in the Fischer projection.

04

Structure of the enantiomers and their respective names

Glucose is an aldohexose. For glucose, the enantiomers are D(+)glucose and L(+)glucose. The structure of both the enantiomers are shown below.

Arabinose is an aldopentose. For arabinose, the enantiomers are D(-) arabinose and L(-)arabinose. The structure of both the enantiomers are shown below.

Erythrose is an aldotetrose. For erythrose, the enantiomers are D(-)erythrose and L(-)erythrose. The structure of both the enantiomers are shown below.

Glyceraldehyde is an aldotriose. For glyceraldehyde, the enantiomers are D(+)glyceraldehyde and L(-)glyceraldehyde. The structure of both the enantiomers are shown below.

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Most popular questions from this chapter

(a) Figure 23-2 shows that the degradation of D-glucose gives D-arabinose, an aldopentose. Arabinose is most stable in its furanose form. Draw D-arabinofuranose.

(b) Ribose, the C2 epimer of arabinose, is most stable in its furanose form. Draw D-ribofuranose.

H. G. Khorana won the Nobel Prize in Medicine in 1968 for developing the synthesis of DNA and RNA and for helping to unravel the genetic code. Part of the chemistry he developed was the use of selective protecting groups for the 5′ OH group of nucleosides.

The trityl ether derivative of just the 5′ OH group is obtained by reaction of the nucleoside with trityl chloride, MMT chloride, or DMT chloride and a base like Et3N. The trityl ether derivative can be removed in dilute aqueous acid. DMT derivatives hydrolyze fastest, followed by MMT derivatives, and trityl derivatives slowest.

(a) Draw the product with the trityl derivative on the 5′ oxygen.

(b) Explain why the trityl derivative is selective for the 5′ OH group. Why doesn’t it react at 2′ or 3′? (c) Why is the DMT group easiest to remove under dilute acid conditions? Why does the solution instantly turn orange when acid is added to a DMT derivative?

Draw the structures of the compounds named in Problem 23-20 parts (a), (c), and (d). Allose is the C3 epimer of glucose and ribose is the C2 epimer of arabinose.

Cytosine, uracil and guanine have tautomeric forms with aromatic hydroxyl groups. Draw these tautomeric forms.

Give an equation to show the reduction of Tollens reagent by maltose.

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