Organic Chemistry Plus Mastering Chemistry with Pearson eText -- Access Card Package (9th Edition) (New in Organic Chemistry)

9th Edition

ISBN: 9780321971128

Author: Leroy G. Wade, Jan W. Simek

Publisher: PEARSON

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Textbook Question

Chapter 23.11, Problem 23.33P

The Wohl degradation, an alternative to the Ruff degradation, is nearly the reverse of the Kiliani—Fischer synthesis. The aldose carbonyl group is converted to the oxime, which is dehydrated by acetic anhydride to the nitrile (a cyanohydrin). Cyanohydrin formation is reversible, and a basic hydrolysis allows the cyanohydrin to lose HCN. Using the following sequence of reagents, give equations for the individual reactions in the Wohl degradation of D-arabinose to D-erythrose. Mechanisms are not required.

a. hydroxylamine hydrochloride
b. acetic anhydride
c. ⁻OH, H₂O

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Chapter 23.11, Problem 23.32P

Chapter 23.11, Problem 23.34P

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Chapter 23 Solutions

Organic Chemistry Plus Mastering Chemistry with Pearson eText -- Access Card Package (9th Edition) (New in Organic Chemistry)

Ch. 23.2 - Prob. 23.1P Ch. 23.3A - Prob. 23.2P Ch. 23.3A - Prob. 23.3P Ch. 23.3B - Draw and name the enantiomers of the sugars shown...Ch. 23.3B - Prob. 23.5P Ch. 23.3C - Prob. 23.6P Ch. 23.4 - Draw the Haworth projection for the cyclic...Ch. 23.4 - Prob. 23.8P Ch. 23.4 - Prob. 23.9P Ch. 23.4 - Prob. 23.10P

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Solution Summary: The author explains the Wohl degradation method, which is an alternative to Ruff degradation. D-arabinose first reacts with hydroxylamine in the presence of hydrochloride to form an oxime.

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Chapter 23 Solutions