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

I apologize for the confusion. Let's break down the reasons why it would be difficult to sort out the factors of base size and alkene stability in the given scenario.

Firstly, methanol (CH3OH) can act as both a solvent and a base. It has the ability to undergo deprotonation to form methoxide ions (CH3O-). Methoxide ions are strong nucleophiles and can react with electrophiles, such as alkyl halides or carbonyl compounds.

On the other hand, potassium t-butoxide (KOC(CH3)3), also known as tert-butoxide, is a strong, bulky base. It is commonly used in elimination reactions, such as the E2 reaction, to generate alkenes.

Now, let's consider the reaction using methanol as the solvent and potassium t-butoxide as the base. Here's the mechanism:

1. The reaction begins with the deprotonation of methanol by t-butoxide:

CH3OH + t-BuO- --> CH3O- + t-BuOH

2. The resulting methoxide ion (CH3O-) can act as a strong nucleophile and attack an alkyl halide or carbonyl compound, leading to the formation of a new bond.

CH3O- + RX --> R-OCH3 + X- (R represents an alkyl group)

Now let's examine why it would be challenging to sort out the factors of base size and alkene stability in this scenario:

1. Base Size: Potassium t-butoxide is a bulky base due to the tert-butyl group (C(CH3)3) attached to the oxygen atom. This steric hindrance makes it less likely to undergo a straightforward nucleophilic attack on or deprotonation of alcohols, compared to a smaller base like hydroxide (OH-). Therefore, it would be difficult to differentiate the effect of base size on the reaction outcome.

2. Alkene Stability: The formation of alkenes strongly depends on the stability of the carbocation intermediate. In this case, the methoxide ion (CH3O-) can react with alkyl halides, leading to the formation of alkenes. However, the specific stability of the resulting alkene formed will depend on the nature and structure of the alkyl halide used. Without controlling the type of alkyl halide or equivalent reactants, it would be virtually impossible to compare and analyze the stability of the resulting alkenes.

To summarize, using methanol as a solvent and potassium t-butoxide as the base complicates the analysis of base size and alkene stability due to the ability of methanol to produce methoxide and the steric hindrance of t-butoxide.