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.

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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.

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What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Ranking Acidity concept. You can view video lessons to learn Ranking Acidity. Or if you need more Ranking Acidity practice, you can also practice Ranking Acidity practice problems.

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

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Solomons 10th Edition. You can also practice Organic Chemistry - Solomons 10th Edition practice problems.