If propionyl chloride is added to one equivalent of methylamine, only a 50% yield of N-methylpropanamide is obtained. If, however, the acyl chloride is added to two equivalents of methylamine, the yield of N-methylpropanamide is almost 100%. Explain these observations.

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
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.29P
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If propionyl chloride is added to one equivalent of methylamine, only a 50% yield of N-methylpropanamide is obtained. If, however, the acyl chloride is added to two equivalents of methylamine, the yield of N-methylpropanamide is almost 100%. Explain these observations.

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