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Answer :
The reaction between nitriles and Grignard or organolithium reagents forms a new C-C bond (Option B) and yields a ketone (Option D). The reaction proceeds through an imine anion intermediate which is hydrolyzed to form the final ketone product.
Conversion of Nitriles to Ketones
The reaction between a nitrile and a Grignard or organolithium reagent, followed by aqueous workup, can be understood through several key points:
- This reaction results in the formation of a new C-C bond (Option B).
- The product of this reaction is a ketone (Option D).
Initially, the Grignard reagent attacks the electrophilic carbon in the nitrile to form an imine anion. This intermediate imine is then hydrolyzed during the aqueous workup to form a ketone. The reaction does not involve an amid tautomer intermediate, and it does not produce an amine.
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This reaction results in the formation of a new C-C bond and The product of this reaction is an amine with a longer carbon chain. The correct options are B) and C).
When a nitrile reacts with a Grignard or organolithium reagent followed by an aqueous workup, it undergoes a nucleophilic addition reaction. The carbon of the nitrile acts as an electrophile, and the carbon of the organometallic reagent acts as a nucleophile. The reaction leads to the formation of a new carbon-carbon (C-C) bond. The resulting product is an amine with a longer carbon chain than the original nitrile. The addition of the organometallic reagent introduces alkyl or aryl groups to the nitrogen atom, extending the carbon chain.
Hence options B and C are correct.
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