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Why is an amide more acidic than amine?...

Why is an amide more acidic than amine?

Text Solution

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The amide has the following resonating structures:

Due to the delocalisation of lone pair of electrons on N over C=O group, amino group acquires a positive charge which makes N—H bond weak. Moreover, the anion formed after removal of a proton is also stabilized by resonance as:

However, no such stabilization is possible in amines.
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