[nonlinear]

What makes a strong base, such as LDA, or TBuO-, non-nucleophilic? I'm still a bit confused about nucleophilicity... I want to be able to recognize non-nucleophilic bases.

Thanks for your *delete me*

[Honclbrif]

Whats the main difference between these bases, and nucleophilic bases such as lithium dimethylamide, or methoxide?

[nonlinear]

I'm not sure... is it that they're so bulky that their nucleophilicity is decreased?

[matt85]

I'm not sure... is it that they're so bulky that their nucleophilicity is decreased?

That's correct. LDA has two bulky isopropyl groups (hence the "D" for di-isopropyl in the LDA acronym) and TBuO- has two bulky tert-butyl groups. Due to this steric hindrance, LDA and TBuO- are not very effective as attacking species (nucleophiles.) However, they are very strong bases, as they are highly-electronegative anionic species.

[azmanam]

this is correct, but tBuO- has only one t-butyl group, not two.

[matt85]

this is correct, but tBuO- has only one t-butyl group, not two.

You're right.

 My bad.