Chapter 3, Problem 44P

As noted in Table 3.1, the $\text{p}{K}_{\text{a}}$ of acetone, ${\text{CH}}_{\text{3}}{\text{COCH}}_3$, is 19.2.

(a) Draw the bond-line formula of acetone and of any other contributing resonance form. (b) Predict and draw the structure of the conjugate base of acetone and of any other contributing resonance form.

(c) Write an equation for a reaction that could be used to synthesize ${\text{CH}}_{\text{3}}{\text{COCH}}_{\text{2}}\text{D}$.