The reaction of 1-chloro-2,4-dinitrobenzene with aqueous to form 2,4-dinitrophenol proceeds via a Me — Aromatic Hydrocarbons Chemistry Question
Question
The reaction of 1-chloro-2,4-dinitrobenzene with aqueous $NaOH$ to form 2,4-dinitrophenol proceeds via a Meisenheimer complex. Which of the following statements about this specific reaction are true?
💡 Solution & Explanation
The $S_NAr$ addition-elimination mechanism is bimolecular (second-order kinetics). In the slow, rate-determining addition step, the nucleophile attacks, changing the target carbon's hybridization from $sp^2$ to $sp^3$. This temporarily disrupts the cyclic aromaticity of the ring (making B false). The $-M$ effect of the ortho/para nitro groups provides vital resonance stabilization to the resulting intermediate carbanion.