Write the mechanism of the reaction of methyl benzoate to form methyl 2-nitrobenzoate.

The question is partially incorrect, because nitration of methyl benzoate results in generation of methyl 3-nitrobenzoate, and not methyl 2-benzoate.

This a because of the present of ester group, which deactivated benzene ring at ortho and para position. Due to this, the electrophile (NO2+) attackes on meta position.

The detailed mechanism is attached below.

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sebassandin sebassandin · Answer 2 · 2019-12-30T16:34:48+01:00

Answer:

See the attached picture.

Explanation:

Hello,

Nitration of alkyl benzenes is carried out adding both nitric and sulfuric acid to the organic reactant in order to promote the inclusion of the nitro group into the ring. Nonetheless, due to the steric hindrance such inclusion is not at the second carbon but at the third one. The addition of nitric acid promotes the attaching of the nitro group and the sulfuric acid shifts the equilibrium towards the nitration is it ionizes the nitric acid to nitronium ion NO₂⁺. The mechanism is shown on the attached picture.

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