JEE Main · ChemistryHard
Which of the following haloarenes is most reactive towards nucleophilic aromatic substitution with sodium methoxide in methanol?
- A.
- B.
- C.
- D.
Show correct answer & step-by-step solution
Correct answer: D —
Solution
- Nucleophilic aromatic substitution proceeds via the formation of a negatively charged Meisenheimer complex.
- The stability of this intermediate is enhanced by electron-withdrawing groups at the ortho and para positions.
- 1-chloro-2,4,6-trinitrobenzene has three nitro groups at the ortho and para positions relative to the chlorine atom.
- This provides the maximum stabilization for the transition state among the given options.
- Hence the answer is (D).
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