Question

Because alcohol protons are reasonably acidic and easily undergo exchange, it is important that the base be matched to the appropriate solvent. Explain why it would be virtually impossible to sort out the factors the size of the base or the stability of the alkenes formed if a reaction were carried out using methanol as the solvent and potassium t-butoxide as the base. In your answer draw a mechanism using methanol and tert-butoxide to illustrate your answer.
I don't understand how to do the mechanism at all. but wouldn't the reasoning have to do with methanol being able to produce methoxide

Answer 1

Potassium tert-butoxide is used to make alkenes by an elimination reaction that does not follow Zaitsev's rule. The compound dissociates into its ionic form, potassium ion and t-butoxide ion. The t-butoxide ion reacts with a haloalkane. Methanol is fairly acidic and it will also dissociate into hydronium and methoxide ions. The methoxide ion will react with the haloalkene and produce a Zaitsev alkene making it difficult to perform the analysis.