JEE Main Chemistry question
Examine the following two structures proposed for the anilinium ion and choose the correct statement: (I) the straightforward structure with attached to an unperturbed benzene ring; (II) an alternative canonical structure showing a positive charge delocalised onto the ring carbon with a neutral group.
Answer: (A)
Solution
In the anilinium ion, all three N–H bonds and the N–C(ring) bond use up nitrogen's entire valence (an octet with no remaining lone pair), so there is no lone pair left on nitrogen that could be pushed into the ring to generate true resonance (canonical) structures with the positive charge delocalised onto a ring
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