In the space below, show a detailed arrow-pushing mechanism for the reaction between the Grignard reagent and methyl benzoate.

Question

11-03-2024
Chemistry

High School

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In the space below, show a detailed arrow-pushing mechanism for the reaction between the Grignard reagent and methyl benzoate.

Answer :

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divya37 divya37 · Answer 1 · 2025-01-24T01:39:45-05:00

Final answer:

The Grignard reagent attacks the carbonyl carbon of the methyl benzoate, forming a tetrahedral intermediate. This intermediate then expels a methoxide ion, reforming the carbonyl and yielding an ion that extracts a proton from the Grignard reagent's alkyl group, generating an alcohol.

Explanation:

Arrow Pushing Mechanism for the Reaction

The Grignard reagent would first be prepared from an alkyl, aryl, or vinyl halide and magnesium in ether or tetrahydrofuran (THF). The resulting Grignard reagent, an organomagnesium compound, is a very strong nucleophile and will easily react with ketones, aldehydes, and esters, like methyl benzoate.

First, the Grignard reagent attacks the carbonyl carbon of the methyl benzoate, breaking the pi bond and forming a new carbon carbon bond. This will yield a tetrahedral intermediate. Then, one of the oxygen carbon bonds swings back down to expel the methoxide ion leaving group, reforming the pi bond. Lastly, the methoxide ion removes a proton from the newly added Grignard reagent alkyl group, generating an alcohol and completing the reaction.

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