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Author: Subject: Do aryl amines react with alkyl halides?
FireLion3
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[*] posted on 7-9-2015 at 01:37
Do aryl amines react with alkyl halides?


Aryl Amines have never been much interest to me, and I wasn't able to find information about this online. Do aryl amines such as aniline, or more activated ones even, react with alkyl halides? I don't know much about aryl amines, but I know aryl halides for instance are super unreactive, for the most part, so I wasn't sure if aryl amines were similar.
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byko3y
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[*] posted on 7-9-2015 at 02:21


Aryl amines are different, they react with alkyl halides.
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UC235
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[*] posted on 7-9-2015 at 12:14


With alkyl halides, the reactive part (the electrophile) is actually the carbon the halogen is attached to, not the halogen itself. In an aryl halide, the carbon is part of an aromatic system and sterically inaccessible. Compare an amine, where the reactive part (the nucleophile) is the nitrogen atom. Aniline is just an amine with a benzene ring stuck to it (which as it turns out does change the properties somewhat, but not nearly as much as for an aryl halide versus an alkyl halide). A better analogue for the comparison would be pyridine, where the reactive bit is embedded in the aromatic ring.
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