Dissociation of HCl in Ethanol: Factors Affecting Ability

[dorebase2006]

In a textbook, HCl is said to remain as molecules in liquid ethanol. However, I still wonder whether HCl dissociates in ethanol to give H⁺ and Cl^- ions.
I think that as ethanol contains an OH group which is polar, ethanol molecules are capable of breaking the bond H-Cl in a manner similar to how polar water molecules do.
Are there any other factors that affect the ability to dissociate of a molecule in a liquid? If so, please provide me with some examples. Thank you in advance.

 

[Borek]

This is an equilibrium process. In water HCl is dissociated (almost) completely, in ethanol it is dissociated only partially. Unfortunately I don't have reliable data on dissociation constant in ethanol at hand (in water it is often listed as 10⁷).

 

[Galap]

To see whether something dissociates to a large extent, we must see whether the initial state or the dissociated state is more stable. In the case of water, HCl and H2O ends up being less stable than chloride and hydronium. However in the case of ethanol, a protonated alcohol has a VERY low pKa, which means that the equilibrium lies to the side of HCl.