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Topic: Why is the Nitration of Aniline so difficult?  (Read 2781 times)

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Offline carotis

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Why is the Nitration of Aniline so difficult?
« on: December 12, 2015, 10:20:17 AM »
hello there! Why is the nitration of Aniline impossible? The Amin group (NH2) can "push" one of its electrone pair into the pi-system,right? So, what happens precisly when trying to nitrate it??
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Offline kriggy

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Re: Why is the Nitration of Aniline so difficult?
« Reply #1 on: December 12, 2015, 10:31:28 AM »
It is so activated that it gets oxidized. Or that is what I have read. You can acetylate the amine and then nitrate
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Offline carotis

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Re: Why is the Nitration of Aniline so difficult?
« Reply #2 on: December 12, 2015, 11:46:04 AM »
well, I think to know the answer now:

Hence the nitration is a reaction under acid conditions, the Aniline would transform into an ammonium. A primary Amine would stand no chance ;) It was a question because of another forum where someone asked about it and I wondered myself, but I think I can go with the answer. :)
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