Compound X was soluble in water and ether, and its aqueous solution turned litmus blue. It reacted with sodium to give a gas. The compound reacted with benzenesulfonyl chloride and base to give an insoluble product, which was unchanged with acidification. It reacted with nitrous acid to give a yellow solid. Compound A could be

Compound X was soluble in water and ether, and its aqueous solution turned litmus blue. It reacted with sodium to give a gas. The compound reacted with benzenesulfonyl chloride and base to give an insoluble product, which was unchanged with acidification. It reacted with nitrous acid to give a yellow solid. Compound A could be

Macroscale and Microscale Organic Experiments

7th Edition

ISBN:9781305577190

Author:Kenneth L. Williamson, Katherine M. Masters

Publisher:Kenneth L. Williamson, Katherine M. Masters

Chapter43: Amines

Section: Chapter Questions

Problem 7Q

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Compound A was oxidized with periodic acid to give B, which after acid hydrolysis gave C. Bromine oxidation of C gave D. Suggest structural formulas, including stereochemistry, for compounds B, C, and D.
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