🤓 Based on our data, we think this question is relevant for Professor Kaur's class at TEMPLE.

Solution: The compound at right has (for obvious reasons) been given the trivial name squaric acid. Squaric acid is a diprotic acid, with both protons being more acidic than acetic acid. In the dianion obtained after the loss of both protons, all of the carbon–carbon bonds are the same length as well as all of the carbon–oxygen bonds. Provide a resonance explanation for these observations.

Problem

The compound at right has (for obvious reasons) been given the trivial name squaric acid. Squaric acid is a diprotic acid, with both protons being more acidic than acetic acid. In the dianion obtained after the loss of both protons, all of the carbon–carbon bonds are the same length as well as all of the carbon–oxygen bonds. Provide a resonance explanation for these observations.