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Chapter 21: Q36P-c (page 1129)

Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.(c)pyrrolidine→N-acetylpyrrolidine

Short Answer

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Synthetic transformation for pyrrolidine to N-acetylpyrrolidine is show as,

Step by step solution

01

Step-by-Step SolutionStep 1: Use of acetyl chloride

Acetic anhydride would work as well as acetyl chloride, a base such as pyridine or sodium bicarbonate or triethylamine is usually added to consume the HCl.

02

Synthesis of N-acetylpyrrolidine from pyrrolidine

When pyrrolidine react with acetyl chloride then there is a formation of N-acetylpyrrolidine as a final product.

In this reaction in the first step base is used to abstract the acidic proton from nitrogen atom and formation of negative charge on the nitrogen atom, In second step negative charge on the nitrogen atom attack the carbonyl carbon of acetyl chloride and there is formation of N-acetylpyrrolidine and hydrochloric acids as a by product.

Formation of N-acetylpyrrolidine

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