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How many more resonating structures does aniline have than anilinium ion?(a) 2(b) 3(c) 4(d) 5I had been asked this question in examination.The question is from Amines Chemical Reactions in portion Amines of Chemistry – Class 12

Answer»

Right CHOICE is (b) 3

To explain I would say: Aniline has five resonating structures, out of which three of them have a positive charge on nitrogen. This RESULTS in unavailability of ELECTRON pair for protonation. When aniline accepts a proton, it FORMS anilinium ion which has only two resonating structures and is less stable and more basic than aniline.



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