MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / Nucleophilic aromatic substitution and benzyne
NEET levelSingle correct optionDifficulty 1 of 3o3166

Which of the following aryl chlorides reacts fastest with sodium methoxide in methanol on moderate heating, by the addition-elimination (SNAr) pathway?

  1. A1-chloro-4-methoxybenzene
  2. Bchlorobenzene
  3. C1-chloro-4-nitrobenzene
  4. D1-chloro-4-methylbenzene

Answer: C

SNAr needs a strongly electron-withdrawing group ortho or para to the leaving group so that the negative charge of the intermediate can be delocalised. Only the nitro compound has such a group. The methyl and methoxy groups donate electrons and chlorobenzene has no activation. The nitro compound reacts fastest.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on Nucleophilic aromatic substitution and benzyne

More questions on Nucleophilic aromatic substitution and benzyne