[Agent-X]

Is there anyway to tell if an ionic compound will be soluble or insoluble in an organic solvent?
I have a table that discusses the solubility of ionic compounds in water, but would the solubility of ionic compounds in an organic solvent be more complex?

[Momer]

Always remember the rule of thumb " Like dissolves like" and don't get confused with the any compound do you have.

Any ionic compound is soluble just in polar or relatively polar solvent, but it couldn't be dissolved in organic solvent because the forces holding the ionic compound molecules to each other (ion-dipole bonds) couldn't be replaced by the Van der Walls interaction which holds up the organic solvent molecules.

But sometimes you could find an ionic compound with a high molecular weight, it could have some solubility in some organic solvent because the large part of the molecule ( as I suggested: has high molecular weight) would dissolve in the organic solvent.

I hope I help you in something..

[Agent-X]

So, the solubility of an ionic compound in an organic solvent depends on the polarity of the solvent. Furthermore, it relates to whether or not the organic solvent can be acidic or basic.

Correct?

How can I tell if the ionic compound will stay ionized or if it will attach to the organic solvent?
Would I need pure knowledge of reaction mechanisms?

[MrTeo]

Any ionic compound is soluble just in polar or relatively polar solvent, but it couldn't be dissolved in organic solvent because the forces holding the ionic compound molecules to each other (ion-dipole bonds) couldn't be replaced by the Van der Walls interaction which holds up the organic solvent molecules.

I'm not very familiar with organic chemistry but I think that if we consider an organic polar solvent it could easily dissolve ionic compounds (I was thinking about CH₃OH) so maybe if you say that "Any ionic compund [...] couldn't be dissolved in organic solvent" you need to specify "organic non-polar solvent". Obviously I could be wrong... just wanted to clarify this statement 

Moreover considering that energies in crystals and in general electromagnetic forces between this sort of compunds are much more stronger than intermolecular van der Waals forces I don't think the 2nd option could really work... neither if we consider the fact that a non-polar solvent has a high molecular weight (which causes these forms of attraction to be stronger because of its higher polarizability).

I think that the key is polarity as you stated with the "like dissolves like" rule or even the presence of ionic bonds in the organic molecule (which would be much more effective) even if i can't recall any ionic organic solvents right now.

So, the solubility of an ionic compound in an organic solvent depends on the polarity of the solvent. Furthermore, it relates to whether or not the organic solvent can be acidic or basic.

Correct?

How can I tell if the ionic compound will stay ionized or if it will attach to the organic solvent?
Would I need pure knowledge of reaction mechanisms?

First of all are you talking about acids and bases of Lewis?

Then I don't think you really need to know the mechanism of a solvatation to decide whether it's possible or not... To make a more precise analysis of the phenomenon I think you would obviously need experimental data and consider temperature, pressure and so on but if you see that the organic solvent it's polar you can say that it will solvate the ionic compound.