p-Chloroanisole is treated with NaNH_2 in liquid ammonia. The major product A is

JEE Main Chemistry question

-Chloroanisole is treated with in liquid ammonia. The major product is

(A)-methoxyaniline ( meta to )
(B)-methoxyaniline ( para to )Correct
(C)-methoxyaniline ( ortho to )
(D)Unreacted -chloroanisole

Answer: (B)

Solution

generates a benzyne intermediate by removing a proton ortho to the chlorine (say C2, equivalent to C6 by the molecule's own symmetry) and expelling chloride, giving a triple bond across C1–C2, where C1 (the original ipso carbon) is para (3 ring bonds) to the at C4 and C2 is meta (2 ring bonds) to it.

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Question ID VK-148096