Question

What is t-butyllithium?

Answer 1

A polar organometallic molecule with significant carbanionic character.

Explanation:

`Bu^(t)Li` contains may be depicted with a formal charge on the carbon centre, i.e. `[{(H_3C)_3C^(-)}Li^(+)]_n`. There is some degree of association to give oligomers, however, this lithium reagent is much less associated than n-butyl-lithium.

Practically, `Bu^(t)Li` is a lot more reactive than `Bu^(n)Li`, and is treated with a lot more respect. Given that the reagent is commercially supplied as an hexanes solution, some due care is warranted, not only in doing the reaction, but also in cleaning up your glassware afterwards.