HCI RC=N + R'OH `NHR' the Ritter reaction

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter8: Addition Via Carbocation
Section: Chapter Questions
Problem 36CTQ
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The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, does not work with primary alcohols.

a. Propose a mechanism for the Ritter reaction.

b. Why does the Ritter reaction not work with primary alcohols?

c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?

HCI
RC=N + R'OH
`NHR'
the Ritter reaction
Transcribed Image Text:HCI RC=N + R'OH `NHR' the Ritter reaction
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