An unknown compound is treated with peroxyacetic acid in dilute sulfuric acid. The product of reaction 1 is reacted with excess PBr3 , then excess NaNH2 (reaction 3). The product of reaction 3 is treated with lithium, then n-butylbromide (reaction 4). In reaction 5 the product of reaction 4 is reacted with ozone, then NaHSO3. This final reaction produced 2 acids, propanoic acid and pentanoic acid. What was the original unknown compouond?

An unknown compound is treated with peroxyacetic acid in dilute sulfuric acid. The product of reaction 1 is reacted with excess PBr3 , then excess NaNH2 (reaction 3). The product of reaction 3 is treated with lithium, then n-butylbromide (reaction 4). In reaction 5 the product of reaction 4 is reacted with ozone, then NaHSO3. This final reaction produced 2 acids, propanoic acid and pentanoic acid. What was the original unknown compouond?

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.50P

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