JEE Main Chemistry question
[IIT 1993] Choose the correct statement regarding the two canonical structures drawn for the anilinium ion — (I) with the positive charge localised on the protonated nitrogen (–N⁺H₃), and (II) an alternative drawn with the charge delocalised onto a ring carbon via an exocyclic C=N⁺ double bond:
Answer: (B)
Solution
Once the nitrogen's lone pair is used to bond the extra proton (forming –NH₃⁺), there is no lone pair left on nitrogen to donate into the ring by resonance; a structure (II) drawn with an exocyclic C=N⁺ double bond would
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