[perivar]

Hello,

What final product would you expect in treating t - butylbenzene with an excess of 2 - chloro - 2 - methylpropane in the precens of a Aluminium chloride catalyst? At the first stages the substitution would give a para or ortho substitut, but as the reaction goes on, does all the hydrogens get substituted?

[Babcock_Hall]

I might be missing something, but are you sure you have the correct reagents?

[discodermolide]

I'm not sure I would expect any product from this.

[perivar]

I'm not sure I would expect any product from this.

Sorry, it should have been 2 - chloro - 2 - methylpropane

[discodermolide]

Alkyl groups are ortho and para directing. The ortho position may well be sterically crowded due to the t-Butyl group. So you are left with para.

[NotExactly]

You'd get 1,4 di-tButyl benzene.  I think you'd get the same product even if you used 1-chloro-2-methyl propane due to carbocation rearrangement. 

[orgopete]

If you have an excess, a third t-butyl group also adds. This product rearranges due to steric hindrance. I believe the final product is the 1,3,5-tri-t-butylbenzene. Perhaps someone could report whether this is correct and the yield.