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Milan Woodson

What is the predominant enol tautomer of 1-phenylbutane-1,3-dione?

In 1-phenylbutane-1,3-dione (1), which enol tautomer will be predominant?

Tautomerism in 1-phenylbutane-1,3-dione

Both carbonyl groups possess α-hydrogens, so can undergo keto-enol tautomerism. In particular, the carbonyl group on the right can enolise in two ways since there are two unique sets of α-hydrogens.

The answer is supposed to be enol 2. Why can't it be either 3 or 4?

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