Identify the major intermediate involved in the following transformation:

Step-by-step solution

The transformation of bromobenzene to aniline using a strong base like KNH ₂ in liquid NH ₃ proceeds via an elimination-addition mechanism. Since there are no strong electron-withdrawing groups on the benzene ring, the reaction does not follow the usual addition-elimination ( S_NAr ) pathway. Instead, the strong base NH ₂^- abstracts an acidic ortho-proton from bromobenzene, leading to the elimination of the bromide ion. This elimination step generates a highly reactive neutral intermediate known as benzyne, which