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 gives the alkoxide : structure

Removing H₂ gives the amide anion : structure

Factor (1) atom is checked before resonance : oxygen versus nitrogen, same period, oxygen is more electronegative and holds the negative charge better. Even though the nitrogen anion is resonance-stabilised, the alkoxide wins on the atom factor, so the O-H proton H₁ is more acidic.

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