Question

Although we normally think of acetic acid as an acid, it can also act as a weak base. Treated with a strong acid, it can became protonated. The conjugate acid of acetic acid is shown below. Derive a resonance structure for this ion which, taken with the given structure, would show that the two - OH groups are equivalent, the two C-O bonds are equivalent, and the positive charge is shared equally by the two oxygens. The skeleton for the second resonance structure is provided below. Add the bond(s), charge(s), and unshared pairs of electrons. For both resonance structures below, draw the curved arrows to show the flow of electrons that transforms them into each other.