When pure *o*-bromoanisole is meticulously treated with strong dissolved in liquid , what is the pre — Haloalkanes and Haloarenes Chemistry Question
Question
When pure *o*-bromoanisole is meticulously treated with strong $NaNH_2$ dissolved in liquid $NH_3$, what is the predominantly isolated major organic product formed exclusively via the benzyne mechanism?
💡 Solution & Explanation
The reaction perfectly proceeds via a highly strained substituted benzyne intermediate. The incoming $NH_2^-$ nucleophile attacks the triple bond to form the most thermodynamically stable carbanion. Because the $-OCH_3$ group strongly exhibits a stabilizing $-I$ effect, the intermediate carbanion positioned closer to the methoxy group is favored, reliably yielding the meta-substituted product (*m*-anisidine).