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Chapter 15: Q76P (page 735)

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.

Short Answer

Expert verified

The reaction of methylamine with propionyl chloride creates a proton that protonates the unreacted amine. This leads to the destruction of amine鈥檚 nucleophilicity. If two equivalents ofCH3NH2 are used, one equivalent remains unprotonated.

Step by step solution

01

Step-by-step-solutionStep 1: Reactions of acid chlorides

Acid chloride combines with alcohol to generate esters. It reacts with water to form carboxylic acid and amines to form amides. For these reactions, the incoming nucleophile is a stronger base than the halide ion that departs.

02

Reaction of methylamine with propionyl chloride

The reaction of methylamine with propionyl chloride creates a proton that protonates the unreacted amine. This leads to the destruction of amine鈥檚 nucleophilicity. If two equivalents of CH3NH2are used, one equivalent remains unprotonated. This reacts as a nucleophile with propionyl chloride to form N-methylproponamide as the product. The reaction can be given as:

Reaction of methylamine with propionyl chloride

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