Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 22, Problem 16PP
Interpretation Introduction

Interpretation:

The name and structures of the aldopentoses are to be represented.

Concept Introduction:

▸ The Kiliani-Fischer reaction is used for producing epimers of higher aldoses from a lower aldose, that is, a single aldose having a lesser number of carbon atoms produces a mixture consisting of two epimeric aldoses with higher number of carbon atoms.

▸ Stereochemistry of sugar compounds: A carbon atom that has four variable groups attached to it is said to be a stereogenic or chirality center of that atom. A stereocenter is that point in a molecule, where any two groups exchange their places to form stereoisomers. Moreover, the pair of diasteromers that show different configuration at the chirality center are called epimers.

▸ The Fischer projection is a way of representing biomolecules with cross formulation of the open chain structures of aldoses such as DGlucose.

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Students have asked these similar questions
A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani–Fischer synthesis, A is converted to two Daldohexoses, B and C. B is oxidized to an optically inactive aldaric acid. C is oxidized to an optically active aldaric acid. What are the structures of A–C?
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.
An aldose A, is reduced by sodium borohydride to an optically inactive alditol B. The Ruff degredation of A forms C. Oxidation of C by nitric acid generates the optically inactive diacid D. The ruff degreation of C forms D-glyceraldehyde. draw the structures for compounds A through D and discuss a mechanism for the reduction step using sodium borohydride
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