JEE Main Chemistry question

ChemistryOrganic Chemistry - Some Basic Principles and TechniquesJEE Main

[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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Question ID VK-140201