Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Jorriss on May 30, 2010, 10:47:19 PM
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Hey guys,
According to a solutions manual, the reaction of aniline with isopropyl chloride (with aluminum chloride) does not react, and I do not see why.
Aniline is an ortho-para activator, so I figured you'd get a mixture of those products.
Thoughts?
Thanks everyone
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Nevermind, I think I figured it out :)
I was only thinking in terms of the resonance. Aniline still has a pretty powerful inductive effect and Friedel-Crafts are not reactive with electron withdrawing groups attached.
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You're on the right track, but it actually isn't the induction that is the problem. Aniline is MUCH more strongly electron donating than withdrawing, so the inductive effect of a nitrogen is far outweighed by the nucleophilicity of the lone pair electrons.
What's the purpose of the AlCl3 in Friedel-Crafts reactions? How does it function in the course of the reaction and why would something like aniline be a problem?
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You're on the right track, but it actually isn't the induction that is the problem. Aniline is MUCH more strongly electron donating than withdrawing, so the inductive effect of a nitrogen is far outweighed by the nucleophilicity of the lone pair electrons.
What's the purpose of the AlCl3 in Friedel-Crafts reactions? How does it function in the course of the reaction and why would something like aniline be a problem?
So the nitrogen is acting as the lewis acid in this case?
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lol, I don't see how to edit my posts.
I meant, lewis base... Sorry for this, mostly, waste of a post =/...
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Yep! You deactivate your catalyst.
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Thanks guys :)