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 6PP
Interpretation Introduction

Interpretation:

The distinguishing test for the given compounds is to be determined.

Concept Introduction:

▸ The pyranoses are six-membered monosaccharide ring structures. The name signifies heterocycle pyran+ose.

▸ Pyranoses are the hemiacetals having ring structures of the D(+)Glucose while glucopyranosides are the carbohydrate acetals called glycosides.

▸ Benedict’s test is a typical chemical method used to oxidize aldoses and ketoses. This particular test can be used as a colorimetric analysis tool and a positive or negative test can help in the distinction of different types of carbohydrates. Tollen’s reagent, which is composed of silver nitrate and ammonia can also selectively oxidize aldehyde and ketone groups present in the carbohydrates. The presence or absence of the oxidized product serves as the basis for the determination of the chemical nature of the compound.

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Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?
β-d-gulopyranose + hydrogen gas and a platinum catalyst.
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