Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Answer the following question about monosaccharide A.

What product is formed when A undergoes a Wohl degradation?

H.
H-
OH
Но
но
H
OH
CH,OH
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Transcribed Image Text:H. H- OH Но но H OH CH,OH
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Introduction

Wohl degradation in carbohydrate chemistry is a chain contract process for aldose.  D-glucose is a short type of dextrorotative glucose. It is one of the two glucose stereoisomers, and it is the one that is biologically active. It exists as a result of photosynthesis in plants. It is the product of the degradation of glycogen in animals and fungi. D-Glucose is among the sixteen stereoisomers of aldohexoses. D-isomer, d-glucose, also known as dextrose, appears commonly in nature, but l-isomer, l-glucose, does not exist. Glucose may be obtained through hydrolysis of carbohydrates such as milk sugar (lactose), cane sugar (sucrose), maltose, cellulose, glycogen, etc.

Explanation

The classic example is the conversion of  D-glucose to arabinose as shown below. The reaction was named after the German chemist Alfred Wohl (1863–1939). Wohl degradation binds the C1 – C2 bond of the aldose chain and lessens it by one carbon. As in the Kiliani–Fischer synthesis, the transition is based on the first conversion of the aldehyde group to cyanohydrin. The ability to decrease (degrade) the aldose chain by one carbon was a significant tool in the carbohydrate elucidation structure. This was normally done by the Ruff technique. An fascinating alternative method, known as the well-being depletion, has also been used. The following equation shows the application of this method to aldopentose, arabinose.

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