Oxaloacetic acid (2-ketosuccinic acid) is a very important intermediate in metabolism. The compound is involved in the citric acid cycle for energy production within the cell. However, the compound is unstable and slowly decomposes spontaneously. Draw the decomposition products.

Carbon dioxide and acetoacetic acid

Explanation:

Oxaloacetic acid is a β-keto acid. It decarboxylates readily via a six-membered cyclic transition state.

The initial products are carbon dioxide and the enol of a ketone.

The enol is unstable and rapidly tautomerizes to the more stable keto form — acetoacetic acid.

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