The nitration of aniline in a strong acidic medium results in the formation of m-nitroaniline because:
In spite of substituents, the nitro group always goes to only the m-position.
In electrophilic substitution reactions, the amino group is meta-directive.
In the absence of substituents, the nitro group always goes to only m-position.
In an acidic (strong) medium, aniline is present as an anilinium ion.
In a strongly acidic medium, the basic amino group () of aniline readily accepts a proton to form an anilinium ion (). While the free amino group is electron-donating and ortho/para-directing, the anilinium ion carries a positive charge on nitrogen, making it strongly electron-withdrawing via the effect. This deactivates the benzene ring and directs the incoming electrophile (nitro group) to the meta-position. Consequently, nitration of aniline in a strongly acidic medium yields a significant proportion of m-nitroaniline.
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