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 3o3208

Which statements about the Meisenheimer complex formed from 1-fluoro-4-nitrobenzene and methoxide are correct?

  1. AThe negative charge is delocalised onto the oxygen atoms of the nitro group
  2. BWith 1-fluoro-3-nitrobenzene the negative charge cannot be placed on the carbon bearing the nitro group, so the corresponding complex is much less stabilised
  3. CFluoride is lost in the same step in which methoxide adds
  4. DThe ring carbon bearing fluorine is hybridised and also bears

Answer: A, B, D

The attacked carbon becomes and the charge is spread over the ortho and para positions and onto the nitro oxygens. For a meta nitro group the charge lies at positions ortho and para to the attacked carbon, none of which is the carbon carrying , so no nitro stabilisation occurs. Addition and loss of fluoride are separate steps, with a distinct intermediate.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on Nucleophilic aromatic substitution and benzyne

More questions on Nucleophilic aromatic substitution and benzyne