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Question

Which one is more acidic?

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Solution

This structures are refers to the image.
In case of acetamide , the most acidic hydrogen of acetamide is NH2. The conjugate base formed by removed of this hydrogen is more stable because nitrogen has larger electronegativity than carbon . On the other hand +I effect of methyl group in acetic acid decrease the acidity of acetic acid. It pushed the electrons to the carbonyl carbon. And electronegativity of electron is less than oxygen.
But the amide could be changed to a carbonylic acid (acedic acid), which is more acidic because Oxygen is more electronegative than Nitrogen.

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