[invain]

If I had a nucleophile, say the conjugate base of benzene, and a molecule with a bromide, and a primary alcohol. Would the nucleophile attack the carbon bound to the bromide, or the proton on the alcohol?

If it's hard to follow I can try to make a picture. Basically I want to add Isobutanol to benzene using a bromide leaving group. (2-bromo-2-methyl-propanol). Possible? I don't know if the alcohol would act like an acid or would the bromide leave first.

[sjb]

If I had a nucleophile, say the conjugate base of benzene, and a molecule with a bromide, and a primary alcohol. Would the nucleophile attack the carbon bound to the bromide, or the proton on the alcohol?

If it's hard to follow I can try to make a picture. Basically I want to add Isobutanol to benzene using a bromide leaving group. (2-bromo-2-methyl-propanol). Possible? I don't know if the alcohol would act like an acid or would the bromide leave first.

Perhaps look into pKa or similar. My feeling is that the benzene anion will act as a base rather than a nucleophile, and if you mix these all you'll get is benzene, and  2-bromo-2-methylpropoxide.

[Honclbrif]

Usually if you are considering a carbon nucleophile, its basic character will dominate over its nucleophilic character if it has a chance to grab an acidic proton. In general, proton transfer is a very fast process. Is there some sort of group you could add to the alcohol oxygen in place of the proton which would be able to withstand the nucleophile, but could be easily removed when you are done with the reaction?

[invain]

Thank you for the replies.

Another questions: Both reactants are soluble in water; If I used aqueous solution, wouldn't I need to buffer the pH pretty high so the benzene anion isn't protonated? If so, would I still need to worry about a protecting group on the alcohol, since it should be deprotonated as well?

[Honclbrif]

Thank you for the replies.

Another questions: Both reactants are soluble in water; If I used aqueous solution, wouldn't I need to buffer the pH pretty high so the benzene anion isn't protonated? If so, would I still need to worry about a protecting group on the alcohol, since it should be deprotonated as well?

You're going to have to brush up on pKa.

[jake.n]

I agree with the sentiment that a phenyllithium or similar benzene nucleophile will grab a proton before displacing the bromide of your electrophile.  You could possibly use 2 equivalents of base (deprotonating both species) or look into palladium cross-coupling for this type of reaction.

And yes, look at your acid/base chemistry to answer your question about using an aqueous solvent.