MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / Nucleophilic aromatic substitution and benzyne
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3207

Which of the following react with sodium methoxide in methanol at by SNAr to replace the halogen with methoxy?

  1. A2-chloro-1,3,5-trinitrobenzene
  2. B1-chloro-2,4-dinitrobenzene
  3. C1-chloro-3,5-dinitrobenzene
  4. D1-chloro-4-methylbenzene

Answer: A, B

Fast SNAr at room temperature needs at least two nitro groups ortho or para to the halogen. These are present in 1-chloro-2,4-dinitrobenzene and 2-chloro-1,3,5-trinitrobenzene. In 1-chloro-3,5-dinitrobenzene both nitro groups are meta to Cl and cannot stabilise the Meisenheimer complex by resonance. 4-Chlorotoluene has no activating group.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on Nucleophilic aromatic substitution and benzyne
Previous questionNext question

More questions on Nucleophilic aromatic substitution and benzyne