Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 22, Problem 26P
Interpretation Introduction

Interpretation:

The structures of D –- psicose and D –- tagatose are to be shown.

Concept Introduction:

▸ Monosaccharides, fructose, sorbose, psicose and tagatose are ketohexoses. Monosaccharides allose and galactose are aldohexoses. All of them are reducing sugars.

▸ Compounds formed by the reaction of reducing sugars with excess of phenylhydrazine are called osazones. Osazones are products of oxidation and are produced by all of the reducing sugars.

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

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Monosaccharide A is a diastereomer of d-lyxose. Treatment of A with nitric acid forms an optically inactive aldaric acid. A undergoes a Kiliani-Fischer synthesis to form B and C. B is oxidized by nitric acid to an optically active aldaric acid, and C is oxidized to an optically inactive aldaric acid. Wohl degradation of A forms D, which is oxidized by nitric acid to an optically inactive aldaric acid. Wohl degradation of D forms a d-aldotriose. Identify A, B, C, and D.
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d-Xylose and d-lyxose are formed when d-threose undergoes a Kiliani–Fischer synthesis. d-Xylose is oxidized to an optically inactive aldaric acid,whereas d-lyxose forms an optically active aldaric acid. What are the structures of d-xylose and d-lyxose?
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