m-Bromoanisole reacts with NaNH_2 in liquid N | vedclass

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Question

(A) The reaction of $m$-bromoanisole with $NaNH_2$ in liquid $NH_3$ proceeds via the benzyne mechanism. The methoxy group $(-OCH_3)$ is an electron-do

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$m$-methoxyaniline

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(A) The reaction of $m$-bromoanisole with $NaNH_2$ in liquid $NH_3$ proceeds via the benzyne mechanism. The methoxy group $(-OCH_3)$ is an electron-donating group by resonance,but it is also electron-withdrawing by the inductive effect. In the benzyne intermediate formed,the nucleophilic attack of $NH_2^-$ occurs at the position that leads to the most stable carbanion. The inductive effect of the $-OCH_3$ group makes the ortho position more acidic and the resulting carbanion at the meta position is more stable due to the proximity of the electron-withdrawing oxygen atom. Consequently,the reaction yields a mixture of $m$-methoxyaniline and $p$-methoxyaniline,with $m$-methoxyaniline being the major product due to the electronic effects of the methoxy group.

$m$-Bromoanisole reacts with $NaNH_2$ in liquid $NH_3$ to give mainly:

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