Chapter 16, Problem 8QP

Oxalic acid $\left({\text{H}}_{\text{2}}{\text{C}}_{\text{2}}{\text{O}}_{\text{4}}\right)$ has the following structure:

An oxalic acid solution contains the following species in varying concentrations: ${\text{H}}_{\text{2}}{\text{C}}_{\text{2}}{\text{O}}_{\text{4}}$ ${\text{HC}}_2{\text{O}}_4^{-},{\text{C}}_2{\text{O}}_4^{2-},{\text{ and H}}_3{\text{O}}^{+}$. (a) Draw Lewis structures of ${\text{HC}}_2{\text{O}}_4^{-},{\text{ and C}}_2{\text{O}}_4^{2-}$ and. (b) Which of the four species can act only as acids, which can act only as bases, and which can act as both acids and bases?