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Chapter 25: Problem 28

Name the two alditols formed by \(\mathrm{NaBH}_{4}\) reduction of D-fructose.

Short Answer

Expert verified
The two alditols formed by the NaBH4 reduction of D-fructose are D-glucitol (sorbitol) and D-mannitol.

Step by step solution

01

Draw the structure of D-fructose

D-fructose is a 6-carbon sugar with the following structure: \[ \small{ \mathrm{HO-CH}_{2}\left(\begin{array}{c} | \\ \mathrm{C} \end{array}\right)\mathrm{O} \left(\begin{array}{c} | \\ \mathrm{CH} \end{array}\right)\mathrm{O}\mathrm{H} \left(\begin{array}{c} | \\ \mathrm{CH}_{2} \end{array}\right)\mathrm{O}\mathrm{H} \left(\begin{array}{c} | \\ \mathrm{CH}_{2} \end{array}\right)\mathrm{O}\mathrm{H} \]
02

Identify the functional group to be reduced

D-fructose contains a carbonyl group (C=O) as the functional group. The carbonyl group can be reduced to an alcohol group (C-OH) by the action of sodium borohydride (NaBH4).
03

Determine the reduction products of D-fructose

Upon reduction using NaBH4, the carbonyl group in D-fructose converts into two different types of alcohol groups: one at the C-1 carbon (primary alcohol) and one at the C-2 carbon (secondary alcohol). This results in the formation of two different alditols.
04

Name the two alditols formed by the reduction of D-fructose

The two alditols formed by the NaBH4 reduction of D-fructose are: 1. D-glucitol, also known as sorbitol, where the primary alcohol is at the C-1 position 2. D-mannitol, where the secondary alcohol is at the C-2 position So, the two alditols formed by the NaBH4 reduction of D-fructose are D-glucitol (sorbitol) and D-mannitol.

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Most popular questions from this chapter

Vanillin (4-hydroxy-3-methoxytenzalclehyde), the principal component of vanilla, occurs in vanilla beans and other natural sources as a \(\beta\)-D-glucopyranoside. Draw it structural formula for this glycoside, showing the D-glucose unit as a chair conformation.

Are \(\alpha\)-D-glucose and \(\beta\)-D-glucose enantiomers? Explain.

One pathway for the metabolism of in-glucose 6-phosphate is its enzyane- catalyzed conversion to D-fructose 6-phosphate. Show that this transforanation can be accomplished as two enzyme-catalyzed keto-enol tautomerisms. O=CC(O)C(O)C(O)C(O)CO D- Glucose 6-phosphate D-Fructose 6-phosphate

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What is the difterence in structure between oligo- and polysaccharides?
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