Complete the curved arrow mechanism for the reaction of 4-methylpentanenitrile and lialh4, followed by the addition of acid to give the major product

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wendy12091 wendy12091

01-04-2022
Chemistry

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Complete the curved arrow mechanism for the reaction of 4-methylpentanenitrile and lialh4, followed by the addition of acid to give the major product

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adioabiola adioabiola · Answer 1 · 2022-04-11T02:25:46-04:00

The curved arrow mechanism for the reaction as described is as represented in the attached image.

Nitrile reduction by LiAlH4

Nitriles, upon reaction with LiAlH4 can be converted to 1° amines.

Opon occurrence of this reaction, the hydride nucleophile attacks the electrophilic carbon in the nitrile to form an imine anion. Once stabilized by a Lewis acid-base complexation the imine salt can accept a second hydride to form a dianion.

On this note, the nitrile reduction of 4-methyl pentanenitrile and lialh4, followed by the addition of acid to give the major product is as represented in the attached image.

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Nitrile reduction by LiAlH4

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