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 2PP
Interpretation Introduction

Interpretation:

The three-dimensional formula for isomer of aldotetrose and ketopentose is to be written and each isomer as D or L sugar is to be designated.

Concept introduction:

Monosaccharides containing 3-carbon atoms are called triose, 4-carbon atoms are called tetrose, 5-carbon atoms are called pentose, and so on.

In chiral molecules, carbon atom having four non-identical substituent groups is called the chirality center of that molecule. Chirality center may also be called stereocenter, which signifies any point in the molecule where the interchanging of any two groups may lead to stereoisomers.

Monosaccharide having its highest chirality center same as that of D (or +)Glyceraldhyde is designated as DSugar, conversely, if the same monosaccharide has its highest chirality center same as that of L (or )Glyceraldhyde, it is designated as LSugar.

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A D-aldopentose A is oxidized to an optically inactive aldaric acid with HNO3. A is formed by the Kiliani–Fischer synthesis of a D-aldotetrose B, which is also oxidized to an optically inactive aldaric acid with HNO3. What are the structures of A and B?
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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.
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