Cyclohexanone reacts with hydroxylamine hydrochloride (NH2OH HCl) to give the oxime product, which upon reaction with sulfuric acid gives the 7-member cyclic amide called caprolactam as the major product. a. Draw both of these reactions. b. Draw mechanisms that account for the formation of the oxime and the cyclic amide. For full credit, you must use the curved arrow notation to show all bond making and bond breaking. You must also show all reactive intermediates.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter23: Addition To A Carbonyl
Section: Chapter Questions
Problem 24E
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Cyclohexanone reacts with hydroxylamine hydrochloride (NH2OH HCl) to give the oxime
product, which upon reaction with sulfuric acid gives the 7-member cyclic amide called
caprolactam as the major product.
a. Draw both of these reactions.
b. Draw mechanisms that account for the formation of the oxime and the cyclic amide. For full
credit, you must use the curved arrow notation to show all bond making and bond breaking.
You must also show all reactive intermediates.
Transcribed Image Text:Cyclohexanone reacts with hydroxylamine hydrochloride (NH2OH HCl) to give the oxime product, which upon reaction with sulfuric acid gives the 7-member cyclic amide called caprolactam as the major product. a. Draw both of these reactions. b. Draw mechanisms that account for the formation of the oxime and the cyclic amide. For full credit, you must use the curved arrow notation to show all bond making and bond breaking. You must also show all reactive intermediates.
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