Amides such as acetamide ( ) are much weaker bases than amines, such as ethylamine (CH3C...

Amides such as acetamide ( ) are much weaker bases than amines, such as ethylamine (CH₃CH₂NH₂).

(a) Use resonance forms to show why the nonbonding electrons on the nitrogen atom of the amide are very

weakly basic.

(b) Strong acid is required to protonate the amide. Predict where acetamide will undergo protonation, and use resonance forms to show why the site you have chosen is more basic. (Hint: To compare basicities, compare the stabilities of the conjugate acids.)