Are alkoxide ions better bases than hydroxide ions?

[Padfoot]

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There's a question that says a stronger base is sometimes needed for the second alkylation of an acetoacidic ester, and the passage shows NaOEt as the first base and NaOH as the second. But I thought that an alkoxide ion should be more basic because its carbon atoms donate more electron density toward the oxygen, making it more basic.

 

[Cawolf]

One could look up the pka of water to be around 15.7 and of ethanol to be around 16.

Since lower pka corresponds to weaker conjugate base, I would've agreed with you and said ethoxide is a slightly stronger base than hydroxide.

I was slightly perplexed by what your passage said so I did a little more reading.

It appears that all alkoxides are stronger bases than hydroxide, with the exception of methoxide - which is slightly weaker.

So I think you are correct and the passage seems off - though in general they are almost equivalent in strength.