1-Chloro-2-(trifluoromethyl)benzene is treated with NaNH2 in liquid NH3. The aryne formed has its triple bond between C-1 and C-6 with the CF3 group on C-2, next to the triple bond. The amide adds so that the developing carbanion is next to the electron-withdrawing group (inductive stabilisation). The major amine is

2,6-bis(trifluoromethyl)aniline

JEE Advanced levelSingle correct optionDifficulty 3 of 3o3199

1-Chloro-2-(trifluoromethyl)benzene is treated with $NaNH X_{2}$ in liquid $NH X_{3}$ . The aryne formed has its triple bond between C-1 and C-6 with the $CF X_{3}$ group on C-2, next to the triple bond. The amide adds so that the developing carbanion is next to the electron-withdrawing group (inductive stabilisation). The major amine is

Elimination uses the only ortho hydrogen (C-6) and gives the aryne between C-1 and C-6. If

NH X_{2} X^{-}

adds to C-1, the carbanion forms on C-6, far from

CF X_{3}

. If it adds to C-6, the carbanion forms on C-1 next to the strongly

- I

group

CF X_{3}

and is more stable. So

NH X_{2}

ends up on C-6, which is meta to

CF X_{3}

, and the product is 3-(trifluoromethyl)aniline.