JEE Main Chemistry question

Replacement of the Cl of chlorobenzene by –OH requires drastic conditions, but the Cl of 2,4-dinitrochlorobenzene is readily replaced (by nucleophilic aromatic substitution), because

(A)–NO₂ makes the ring electron-rich at the *ortho* and *para* positions
(B)–NO₂ withdraws electron density at the *meta* position
(C)–NO₂ donates electron density at the *meta* position
(D)–NO₂ withdraws electron density (by resonance) at the *ortho* and *para* positions, directly stabilising the Meisenheimer intermediate at the ipso carbon bearing ClCorrect

Answer: (D)

Solution

In 2,4-dinitrochlorobenzene the two nitro groups sit *ortho* and *para* to the chlorine, exactly the positions from which they can withdraw electron density by resonance from the

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Question ID VK-140337