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Chemistry / Organic Chemistry 7 / Chapter 21 / Problem 42P

Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice

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A hexose was obtained after (+)-glyceraldehyde underwent

Chapter 21, Problem 42P

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Problem 42P

A hexose was obtained after (+)-glyceraldehyde underwent three successive Kiliani–Fischer synthesis. Identify the hexose from the following experimental information: oxidation with nitric acid forms an optically active aldaric acid; a Wohl degradation followed by oxidation with nitric acid forms an optically inactive aldaric acid; and a second Wohl degradation forms erythrose.

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QUESTION:

Problem 42P

A hexose was obtained after (+)-glyceraldehyde underwent three successive Kiliani–Fischer synthesis. Identify the hexose from the following experimental information: oxidation with nitric acid forms an optically active aldaric acid; a Wohl degradation followed by oxidation with nitric acid forms an optically inactive aldaric acid; and a second Wohl degradation forms erythrose.

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