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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Answer ALL parts of this question. (a) Provide the structure and name of the aldehyde with the formula, C2H4O. (b) Draw the two steps of the Strecker synthesis used for the conversion of the aldehyde in part (a) into racemic alanine. (c) Draw the (R) and (S) enantiomers of alanine. Which is the naturally occurring enantiomer? (d) Draw the structure of the dipeptide, Ala-Gly.
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.
Draw a diagram of the linear and ring structures of glucose. Show the biochemical mechanism of cyclization of each and name the resultant ring – including the ring type & anomeric carbon designation. Draw and name an amine version, reduced version, and oxidized version, either in ring or Fisher projection.
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