Question

The major product (F) in the following reaction is

• A. o-Anisidine
• B. m-Anisidine
• C. p-Anisidine
• D. p-Chloro aniline

Hint:

Using a simple frame or just bolding for the box Key Points: Reaction of aryl halides lacking strong EWGs with NaNH$_2$/liq NH$_3$ proceeds via benzyne mechanism (Elimination-Addition). Benzyne formation involves deprotonation ortho to the leaving group, followed by elimination of the leaving group. Nucleophilic addition to the benzyne is regioselective, often guided by the inductive effects of substituents. Electron-withdrawing groups (like -OCH$_3$ via -I effect) direct the incoming nucleophile meta to themselves to best stabilize the intermediate carbanion. The product is m-anisidine.