I am thinking about a chemical reaction of 2-Bromo-2-methylbutane with tert-butyl alcohol and heat, assuming elimination products. I am thinking this reaction will be E1 because it is a tertiary halide and tert-butanol is a very weak base, and fairly polar and also protic. If it is a pure E1 reaction, would we see the same favoring of the Hoffman product that is seen with an E2 reaction with tert-butoxide?
I have heard that E1 reactions give Zaitsev products regardless of steric hindrance on the base, perhaps because the transition state to form the alkene is very late due to Hammond's postulate. But I don't know if this is always true. And perhaps in this case the mechanism is a concerted hybrid of E2 and E1, with an asynchronous transition state, because tert-butanol is not polar enough to allow for carbocation formation. If I just knew the experimental outcome I could backwards justify it.