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Which is the most stable tautomer out of these compounds?

Which is the most stable tautomer out of these compounds?

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Grade:11

1 Answers

Yusuf Hasan
16 Points
5 years ago
From what I could understand, I think that you are trying to ask where the equilibrium of the keto-enol tautomerism is going to shift. If we look at spontaneity, the second compound will undergo three successive enolizations to form 1,3,5 trihydroxybenzene, while the first compound will
immediately undergo a single enolization from the methyl substituted end to form an enol to minimize dipolar repulsions from the carbonyl oxygens. Assuming thermodynamic control, I would say that more of the aromatic compound would be formed, so the first option would be my answer. 

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