High School

Treatment of a nitrile group with a Grignard reagent followed by hydrolysis results in what product?

Answer :

When a nitrile group (also known as a cyano group) is treated with a Grignard's reagent followed by hydrolysis, it undergoes a chemical transformation known as hydrolysis of nitriles. This reaction produces a carboxylic acid.

Grignard's reagents are organomagnesium compounds that react with nitriles to form a metal cyanide intermediate. The general reaction can be represented as:

R-CN + RMgX → R-C≡N:MgX

(Nitrile) (Grignard's reagent) (Metal cyanide intermediate)

The metal cyanide intermediate formed is unstable and reacts further with water (hydrolysis) to yield a carboxylic acid:

R-C≡N:MgX + H₂O → R-COOH + MgXOH

(Metal cyanide intermediate) (Carboxylic acid) (Magnesium hydroxide)

In this reaction, the carbon-nitrogen triple bond (C≡N) of the nitrile group is transformed into a carboxylic acid group (COOH) through the addition of water.

The Grignard's reagent acts as a nucleophile, attacking the nitrile carbon and forming the intermediate. Hydrolysis of the intermediate with water then replaces the metal atom (Mg) with a hydrogen atom, resulting in the formation of the carboxylic acid.

Overall, the treatment of a nitrile group with a Grignard's reagent followed by hydrolysis leads to the conversion of the nitrile into a carboxylic acid.

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