Chapter 27, Problem 22P

(a) The two most acidic hydrogens of uracil have $\text{p}{K}_{\text{a}}\text{'s}$ of $9.5$ and $14.2$, respectively. Match these $\text{p}{K}_{\text{a}}\text{'s}$ with the hydrogens in the structural formula and provide structures for the stable resonance contributors of the monoanion and the dianion.

(b) The $\text{p}{K}_{\text{a}}$ of the conjugate acid of triethylamine is $10.4$. Is triethylamine a strong enough base to convert uracil to its monoanion? To its dianion.