[hobobot]

I went to a party full of chem majors the other day and a sophomore asked me a question I couldn't remember how to do. (mostly because it's been a year since my last chem class)
anyway let's pretend we have 4-methylphenol and I want to add two tert-butyls ortho to the OH group.
Will FC work? Or is t-butyl too big?
Someone said something about mixing an acid with t-butanol but I wasn't sure what that was all about.

[Honclbrif]

Looks like it could be possible, but the yield would probably suck due to the crowding. Having a phenol OH in there probably wouldn't be the best conditions either.

But on to the other question: what's the mechanism of FC alkylation? What happens when you mix a strong acid with tBuOH? There's another way to generate the same reactive species without using any leaving groups at all.

[hobobot]

you mean make the cation by dehydrating TbutOH?...ahh I get it now. Wasn't thinking about how it's a tertiary carbon. that would totally work. Thank you!