[gingi85]

Predict the products of the reaction of 3-bromo-2,3,4-trimethylpentane with hydroxide ion.

Clearly, this cannot react through SN2, b/c the carbon is tertiary. However, it seems reasonable that both an SN1 and E2 reaction are possible to produce 2,3,4-methyl-3-pentanol and 2,3,4-methyl-2-pentene, respectively. The latter product could also be produced through a competing E1 reaction. Can all these mechanisms be taking place simultaneously?

Thank you.

[Yggdrasil]

All three are taking place at the same time, but not at the same rate.  Because carbocation formation is a fairly slow process, the concerted E2 reaction will proceed at a faster rate than the E1 and SN1 reactions, so your major product will be the elimination product.