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Compare th relative acidic strengths of hydroxyl amine and am oxime.

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Both contain image group in their molecules and are expected to be weakly acidic. However, oxime is actually more acidic. Infact, hydroxyl amine after losing a proton forms a conjugate base in which negative charge is localised only on the oxygen atom.
image
However, in case of oxime, the negative charge gets delocalished by extending `pi` electron bonding.
image

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