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 formation of a benzyne intermediate. $1$. $KNH_2$ acts as a stron

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 formation of a benzyne intermediate. $1$. $KNH_2$ acts as a strong base and removes an ortho-hydrogen from $p$-chlorotoluene to form a benzyne intermediate. $2$. The nucleophilic attack by $NH_2^-$ can occur at either the carbon atom originally attached to the chlorine or the adjacent carbon. $3$. Due to the inductive effect of the methyl group,the attack results in a mixture of $p$-toluidine and $m$-toluidine. $4$. In this specific reaction,$m$-toluidine is often formed as a significant product due to the regioselectivity of the nucleophilic attack on the benzyne intermediate.

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

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