Compare the two protons H₁ and H₂ shown in the following compound and identify which proton is more acidic.

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Removing H₁ (α to the carbonyl) gives an enolate : structure

Removing H₂ gives an ordinary carbanion : structure

The enolate is resonance-stabilised, with most of the negative charge on the electronegative oxygen. The other anion is localised on carbon with no resonance. The α proton H₁ is much more acidic.

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