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Chapter 21: Q36P-d (page 1129)

Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.(d)γ-aminobutyricacid→pyrrolidine

Short Answer

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Synthetic transformation for γ-aminobutyric acid to pyrrolidine is show as,

Step by step solution

01

Step-by-Step SolutionStep 1: Use of LiAIH4 reagent

LiAIH4is a strong reducing agent for polar double bonds, as it easily thought of as a source of H− . It will reduce aldehydes, ketones,esters, carboxylic acid chloride, carboxylic acids and even carboxylate salts to alcohols.

LiAIH4is also reduce the amide and nitriles to amine, In above reaction amide is reduce to amine.

02

Synthesis of pyrrolidine from gamma-aminobutyric acid

In gamma-aminno butyric acid the nitrogen attack on the carbonyl carbon of acid and there is a formation of cyclic amide in the first step and there is removal of water molecule.

In the second step cyclic amide is react with the strong reducing reagent LiAIH4andH2O then there is a formation of amine i.e. pyrrolidine.

Formation of pyrrolidine

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