While heavily restricted in aqueous systems, alkyl halides tend to be highly miscible and soluble in — Haloalkanes and Haloarenes Chemistry Question
Question
While heavily restricted in aqueous systems, alkyl halides tend to be highly miscible and soluble in common non-polar or weakly polar organic solvents like benzene, ether, and chloroform. What is the fundamental thermodynamic reason verifying this high organic solubility?
💡 Solution & Explanation
Solubility obeys the thermodynamic principle of "like dissolves like." Alkyl halides are held together by moderate dipole-dipole and van der Waals forces, much like typical organic solvents. When an alkyl halide dissolves in an organic solvent, the energy required to break the solute-solute and solvent-solvent interactions is almost perfectly compensated by the formation of new, structurally similar solute-solvent interactions. Because the enthalpy of mixing ($\Delta H_{mix}$) is very close to zero, the process is enthusiastically driven forward by the highly favorable increase in the entropy of mixing ($\Delta S_{mix} > 0$).