[Kate]

Hello.

Can a tertiary ammonium salt and dichlomethane react?

I've seen that tertiary amines can indeed react with halogenated solvents, but no idea if when the amine is protonated and in "salt form" it can happen. Anybody got any experience with this?

Thanks.

[phth]

Certainly.  All thats required is Sn1 and Sn2 substitution by a base first creating a tert amine.  This only means that it will happen slower.

[Babcock_Hall]

An ammonium ion is not a nucleophile at all.  Maybe I am not understanding your question.

[Kate]

Certainly.  All thats required is Sn1 and Sn2 substitution by a base first creating a tert amine.  This only means that it will happen slower.

Thanks.

Got another question: should reactions with amines not be carried out in dichloromethane as a solvent then?

An ammonium ion is not a nucleophile at all.  Maybe I am not understanding your question.

Yes, I know. But i was thinking that maybe in solution, proton exchange between the ammonium ion and water or some base could deprotonate the ion and then reaction might occur with dichloromethane.

Actually, do you know the extent, if any, to which a tertiary ammonium ion might undergo proton exchange with water? (amines are more basic than water, but still...). Also, do you have any experience of reactions with amines using dichloromethane as a solvent? Can cross-products appear?

I'm talking about this because what I'm doing in lab is somehow coming up wrong.