In Chapter $3,$ we will explore the factors that render compounds acidic or basic. Tropolone $(1)$ is a compound that is both fairly acidic and fairly basic $($J$.$ Org. Chem. $1997,62,3200-3207).$ It is acidic because it is capable of losing a proton $(H^{+})$to form a relatively stable anion $(2),$ while it is basic because of its ability to receive a proton to form cation $3$:

Draw all significant resonance structures of anion $2$ and of cation $3$ and explain why each of these ions is stabilized.