[unistudent]

1. What happens to an acetic acid molecule when it is dissolved in (a) ether and (b) 5% aqueous NaOH.

2. What happens to a triethylamine molecule when it is dissolved in (a) ether and (b) 5% aqeous HCl.

Here were my thoughts:
 For 1b) the acid would lose an H and the base would lose and OH to form water and thus the Na+ joined the negative acid molecule to form the other compund but I don't know what the effects would be on ether.
 For 2 I have  no idea because I thought that triethylamine is an acid so I don't know what its effects would be on ether of HCL.

I don't know if this helps but we used diethyl ether in our experiment testing other substances.

Thanks for any and all help.

[ardbeg]

triethylamine is a base.  does that help?

you are correct in 1b btw.

[Cancer Boy]

For dissolving in ether, forget the acidity and basicity of the molecules. Just bear in mine triethylamine and acetic acid are organic compounds and diethyl ether is an organic solvent

[orgopete]

For amines, you may find pKa values of the conjugate acids. The fact that the conjugate acid is being referred to may not always be appreciated.

If you look at the tables linked in Rich's web site, http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf (p 14-16), you will find some amines listed as ammonium salts, and other not. Triethylamine is listed with a pKa of 10.65. Obviously, this is the ammonium salt of triethylamine.

I think some textbooks list two pKa values for primary and secondary amines. Obviously if this is done for the amine itself, then they are referring to the conjugate acid. If anyone is confused by this, you are probably not alone.