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Identify the correct order of basic strength of the following substituted anilines?(a) p-Methylaniline > m-Methylaniline > p-Nitroaniline > m-Nitroaniline(b) p-Methylaniline > m-Methylaniline > m-Nitroaniline > p-Nitroaniline(c) p-Nitroaniline > m-Nitroaniline > p-Methylaniline > m-Methylaniline(d) p-Nitroaniline > m-Nitroaniline > m-Methylaniline > p-MethylanilineThe question was posed to me during an interview.This is a very interesting question from Amines Chemical Reactions in chapter Amines of Chemistry – Class 12

Answer»

Right choice is (b) p-Methylaniline > m-Methylaniline > m-Nitroaniline > p-Nitroaniline

The explanation is: The BASE WEAKENING effect of electron withdrawing group (NO2) and the base strengthening effect of electron DONATING group (CH3) is more prominent at para position than at meta position.



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