[Jorriss]

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

[Jorriss]

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.

[Doc Oc]

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?

[Jorriss]

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?

[Jorriss]

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

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

[nj_bartel]

Yep!  You deactivate your catalyst.

[Jorriss]

Thanks guys