JEE Main Chemistry question

1-Fluoro-4-nitrobenzene is treated with dimethylamine in DMF under heating to give a product : [IIT JEE 2003]

p-F-- A

(A) (nitro group already reduced)
(B) (-dimethyl-4-nitroaniline)Correct
(C)2-Fluoro-5-nitro--dimethylaniline
(D) (fluorine retained, nitro displaced)

Answer: (B)

Solution

The strongly electron-withdrawing para-nitro group activates the C–F carbon toward nucleophilic aromatic substitution () via a resonance-stabilised Meisenheimer intermediate, and fluorine (despite being a poor leaving group in ) is an excellent leaving group in because of its high

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Question ID VK-150247