Question

Which is the stronger base among `"NaOEt"` (sodium acetate) and `"LDA"` (lithium diisopropylamide)?

Answer 1

In decreasing basicity

`"LDA" > "NaOEt" > "NaOAc"`

Explanation:

Sodium acetate is written as `"NaOAc"`, with chemical formula

https://upload.wikimedia.org/wikipedia/commons/4/45/Sodium-acetate-2D-skeletalpng

Not `"NaOEt"`, which is called sodium ethanoxide and has a chemical formula

https://upload.wikimedia.org/wikipedia/commons/4/4a/Sodium_ethoxidepng

`"NaOAc"` is not a strong base as the negative charge can be delocalized among the 2 oxygens.

To compare whether `"LDA"` or `"NaOEt"` is more basic, we can consider two reactions

1. Ethanol + LDA.

2. Sodium ethanoxide + diisopropylamine (conjugate acid of LDA)

The first reaction proceeds much further than the second one.

LDA can only be formed from treatment of diisopropylamine with n-butyllithium, which is much more basic than sodium ethanoxide.

From this, we conclude that LDA is more basic than sodium ethanoxide.

So the final result, in decreasing basicity

`"LDA" > "NaOEt" > "NaOAc"`

For stronger evidence, please refer to their `"p"K_"a"` values.