How to pronounce“alkoxides”in English

However, with weaker bases, like alkoxides, the pKa of the base and the enolate are close.

They’re very electronegative, relatively small, and not very polarizable – think fluorides, alkoxides, organolithiums, and Grignard reagents.

And really strong nucleophiles are often charged, so thiolates, hydroxide, and alkoxides are all examples of strong bullies… or nucleophiles… that use SN2 mechanisms.

So if we deprotonate an alcohol, we make an alkoxide, the negatively charged conjugate base, which is an excellent nucleophile.