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Chapter 23: Q11P (page 1218)

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.

Short Answer

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furanose structure of the product

Step by step solution

01

Epimers

Sugars which have the common configuration like the arrangement of H - and - OH around carbon atoms are same except the carbon present at 伪 position or carbon number 2 are known as epimers. For example, glucose and mannose are epimers of each other.

02

Fructose

Fructose is a ketohexose which contain a ketone group. It is used as a sweetening agent in many confectionaries and also as a substitute of cane sugar.

03

Furanose

Furanose is a five-membered cyclic hemiacetal whose name is derived from the five-membered cyclic ether furan. Five membered ring of fructose is known as fructofuranose.

04

The reaction forming the furanose structure

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Most popular questions from this chapter

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.

Except for the Tollens test, basic aqueous conditions are generally avoided with sugars because they lead to fast isomerizations.

  1. Under basic conditions, the proton alpha to the aldehyde (or ketone) carbonyl group is reversibly removed, and the resulting enolate ion is no longer asymmetric. Reprotonation can occur on either face of the enolate, giving either the original structure or its epimer. Because a mixture of epimer results, this process is called epimerization. Propose a mechanism for the base-catalyzed equilibration of glucose to a mixture of glucose and its C2 epimer, mannose.
  2. Propose a mechanism for the isomerization of a ketose to an aldose, via the enediol intermediate, shown immediately above. Note that the enediol has twoprotons and removing one or the other gives two different enolate ions.

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

Aldohexoses A and B both undergo Ruff degradation to give aldopentose C. On treatment with warm nitric acid, aldopentose C gives an optically active aldaric acid. B also reacts with warm nitric acid to give an optically active aldaric acid, but A reacts to give an optically inactive aldaric acid. Aldopentose C is degraded to aldotetrose D, which gives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D is degraded to (+)-glyceraldehyde. Deduce the structures of sugars A,B,C and D, and use Figure 23-3 to determine the correct names of these sugars.

Question: Propose a mechanism for methylation of any one of the hydroxy groups of methyl-伪-D-glucopyranoside,using and dimethyl sulfate.
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