Chapter 2, Problem 2.22P

The $\text{C}-\text{H}$ bond in acetone, ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}=\text{O}$, has a $\text{p}{K}_{\text{a}}$ of $19.2$. Draw two

resonance structures for its conjugate base. Then, explain why acetone is much more acidic than propane, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}\left(\text{p}{K}_{\text{a}}=50\right)$.