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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Jorriss on May 30, 2010, 10:47:19 PM

Title: Aniline + Isopropyl Chloride
Post by: Jorriss on May 30, 2010, 10:47:19 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

Title: Re: Aniline + Isopropyl Chloride
Post by: Jorriss on May 30, 2010, 11:26:18 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.

Title: Re: Aniline + Isopropyl Chloride
Post by: Doc Oc on May 30, 2010, 11:54:02 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?

Title: Re: Aniline + Isopropyl Chloride
Post by: Jorriss on May 31, 2010, 01:50:11 AM

Quote from: J-bone on May 30, 2010, 11:54:02 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?

So the nitrogen is acting as the lewis acid in this case?

Title: Re: Aniline + Isopropyl Chloride
Post by: Jorriss on May 31, 2010, 03:30:34 AM

lol, I don't see how to edit my posts.

I meant, lewis base... Sorry for this, mostly, waste of a post =/...

Title: Re: Aniline + Isopropyl Chloride
Post by: nj_bartel on May 31, 2010, 03:49:07 AM

Yep!  You deactivate your catalyst.

Title: Re: Aniline + Isopropyl Chloride
Post by: Jorriss on May 31, 2010, 11:09:09 AM

Thanks guys :)