Question #44167

Consider the hydration equilibria of propan-2-one (Acetone) and 1,1,1,3,3,3-hexafluoropropan-2-one (HFA) in aqueous solution at 298 K. Generally, ketone hydration is disfavored due to steric hindrance (B-strain) in the $sp^3$ hybridized gem-diol. Consequently, the standard Gibbs free energy of hydration for acetone is $+17.1 \text{ kJ mol}^{-1}$. However, for HFA, the massive inductive withdrawal (-I) of the fluorine atoms and the relief of $sp^2$ dipole repulsion completely overcome the steric B-strain, yielding a standard Gibbs free energy of hydration of $-34.2 \text{ kJ mol}^{-1}$. What is the ratio of their hydration equilibrium constants, $\frac{K_{HFA}}{K_{Acetone}}$, at 298 K? (Given: $2.303 RT = 5.7 \text{ kJ mol}^{-1}$ at 298 K)