Question
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.
This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Amines. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.
More Amines Questions
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