[Anooshir]

Friedel-Crafts alkylation of an activated benzene molecule (1,4-dimethoxybenzene) occurs with a tertiary alcohol (t-butyl alcohol) in the presence of sulfuric acid as the Lewis acid catalyst to form 1,4-di-t-butyl-2,5-dimethoxybenzene.  The question is:  Suggest two other compounds that might be used in place of t-butyl alcohol to form 1,4-di-t-butyl-2,5-dimethoxybenzene.  I am having a lot of trouble with this question and am totally stumped; I would greatly appreciate any assistance in answering this question.  Thank you.

[AWK]

What about isobutene (2-methylpropene)?

[Dan]

You just need a source of the t butyl cation - so you could change the leaving group...

[Yggdrasil]

Basically the question wants you to know/realize that in F-C alkylations, the reaction between your Lewis acid and your alkyl donor produces a carbocation and that these carbocations will undergo intramolecular rearrangements before reacting with your aromatic molecule.  So, AWK's suggestion is a good one (although Dan's is much simpler).

[AWK]

Using isobutene and H2SO4, t-butyl hydrogen sulfate is obtained - hence the leaving group is HSO4- - this is a special case of Dan suggestion