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Author Topic: Aniline + Isopropyl Chloride  (Read 3097 times)

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Jorriss

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Aniline + Isopropyl Chloride
« on: May 30, 2010, 04:47:19 PM »

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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Jorriss

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Re: Aniline + Isopropyl Chloride
« Reply #1 on: May 30, 2010, 05:26:18 PM »

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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Doc Oc

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Re: Aniline + Isopropyl Chloride
« Reply #2 on: May 30, 2010, 05:54:02 PM »

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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Jorriss

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Re: Aniline + Isopropyl Chloride
« Reply #3 on: May 30, 2010, 07:50:11 PM »

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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Jorriss

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Re: Aniline + Isopropyl Chloride
« Reply #4 on: May 30, 2010, 09:30:34 PM »

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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nj_bartel

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Re: Aniline + Isopropyl Chloride
« Reply #5 on: May 30, 2010, 09:49:07 PM »

Yep!  You deactivate your catalyst.
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Jorriss

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Re: Aniline + Isopropyl Chloride
« Reply #6 on: May 31, 2010, 05:09:09 AM »

Thanks guys :)
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