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The Meisenheimer complex formed during SNAr substitution is a resonance-stabilized carbanion. Which Aromatic Hydrocarbons Chemistry Question

Question

The Meisenheimer complex formed during SNAr substitution is a resonance-stabilized carbanion. Which of the following groups must be present at the ortho or para positions to sufficiently lower the activation energy for its formation?

Answer: D

💡 Solution & Explanation

Strong EWGs accept and heavily delocalize the negative charge of the carbanion intermediate. A para $-NO_2$ group allows the negative charge to be pushed entirely out of the ring onto highly electronegative oxygen atoms.

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