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Protonation of an amide using strong acid occurs on oxygen rather than on nitrogen. Suggest a reason for this behavior, taking resonance into account.
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When a strong acid donates a proton to the amide, both the oxygen and nitrogen atoms are potential sites for protonation due to their lone pair of electrons. Show more…
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Protonation of an amide using strong acid occurs on oxygen rather than on nitrogen. Suggest a reason for this behavior, taking resonance into account. (TABLE CANNOT COPY)
In general, nitrogen atoms are more basic than oxygen atoms. However, when an amide is treated with a strong acid such as sulfuric acid, it is the oxygen atom, rather than the nitrogen atom, that is protonated. Protonation of the oxygen atom gives a cation that is not resonance stabilized but is stabilized by induction. In contrast, protonation of the nitrogen atom gives a cation that is resonance stabilized but not stabilized by induction.
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