[gavindor]

nBuli + H2O, and whether nBuli is a bronsted base?

This reaction-

n-BuLi + H2O → nBuH + LiOH

I understand is

C4H9Li + H2O --> C4H10 + LiOH

And I understand that n-Buli(C4H9Li)  is in a solvent but is not forming solvated ions. It's a molecule, it's covalent.

What i'm wondering is whether or not it's a bronsted base.
 
The conjugate pairs don't quite work..

C4H9Li/C4H10   <-- The Li has gone..

H2O/LiOH <-- An Li has been gained.

And we can't cancel the Li out as a spectator ion, because it's part of the n-Buli(C4H9Li) molecule, it's not a spectator ion.

Thanks

[Babcock_Hall]

https://en.wikipedia.org/wiki/N-Butyllithium#:~:text=In%20the%20case%20of%20n,%5BCH2R%5D4.

I don't have specific thoughts regarding your question; I do, however, have a general comment.  Although we write nBuLi as if it were a simple, covalent compound, it aggregates in solution.

[Hunter2]

Butyllithium is a strong base pka 50 stronger as hydroxide pka 15.7.
The reaction with water is an exchange reaction of Li to H.


https://www.uwindsor.ca/people/jgreen/sites/uwindsor.ca.people.jgreen/files/pka_bases.pdf

[gavindor]

Butyllithium is a strong base pka 50 stronger as hydroxide pka 15.7.
The reaction with water is an exchange reaction of Li to H.


https://www.uwindsor.ca/people/jgreen/sites/uwindsor.ca.people.jgreen/files/pka_bases.pdf

Thanks.

From what I understand,  in an exchange reaction, https://open.oregonstate.education/aandp/chapter/2-3-chemical-reactions/ both symthesis and decomposition occur e.g. A+BC→AB+C.

But isn't that the case with any acid base reaction?  e.g. if a proton leaves the acid and goes to a base, then that's an exchange reaction?

Or did you just mean that it's a chemical reaction involving a proton exchange?

I'm wondering whether  you would call n-BuLi + H2O → nBuH + LiOH a bronsted lowry reaction?  Or not, because one can't identify conjugate pairs?

And i'm wondering where you would call it a neutralisation reaction, given that while some neutralisation took place, NaOH is still a strong base. so the product is far from neutralised?

[Hunter2]

But isn't that the case with any acid base reaction?  e.g. if a proton leaves the acid and goes to a base, then that's an exchange reaction?

Or did you just mean that it's a chemical reaction involving a proton exchange?

I would say the second one.

I'm wondering whether  you would call n-BuLi + H2O → nBuH + LiOH a bronsted lowry reaction?  Or not, because one can't identify conjugate pairs?

Can not identify  conjugate pairs.

And i'm wondering where you would call it a neutralisation reaction, given that while some neutralisation took place, NaOH is still a strong base. so the product is far from neutralised?

Neutralisation guides to the middle of pH scale, means  in aqueous solution pH 7. Here only a stronger base exchanged to a weaker one.

[gavindor]

Neutralisation guides to the middle of pH scale, means  in aqueous solution pH 7. Here only a stronger base exchanged to a weaker one

Thanks, that makes sense

I'm wondering whether  you would call n-BuLi + H2O → nBuH + LiOH a bronsted lowry reaction?  Or not, because one can't identify conjugate pairs?

Can not identify  conjugate pairs.

Thanks, I know for sure that we can't identify conjugate pairs.

But to clarify, would you say  n-BuLi + H2O → nBuH + LiOH is thus not a bronsted lowry reaction?

[Hunter2]

I would say so.