In the reaction of p-chlorotoluene with KNH_2 | vedclass

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(B) The reaction of $p-$chlorotoluene with $KNH_2$ in liquid $NH_3$ proceeds via the benzyne mechanism.$1$. The strong base $NH_2^-$ abstracts an orth

Vedclass · Accepted Answer

$m-$Toluidine

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(B) The reaction of $p-$chlorotoluene with $KNH_2$ in liquid $NH_3$ proceeds via the benzyne mechanism.$1$. The strong base $NH_2^-$ abstracts an ortho-hydrogen from $p-$chlorotoluene to form a benzyne intermediate.$2$. The benzyne intermediate is $4-$methylbenzyne.$3$. The nucleophilic attack by $NH_2^-$ can occur at either the $meta$ or $para$ position relative to the methyl group.$4$. Attack at the $meta$ position leads to $m-$toluidine,while attack at the $para$ position leads to $p-$toluidine.$5$. Due to the inductive effect of the methyl group,the $meta$ position is more electrophilic,making $m-$toluidine the major product.

In the reaction of $p-$chlorotoluene with $KNH_2$ in liquid $NH_3,$ the major product is :

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