The hydrolysis of an amide often requires harsh conditions, high temperatures, or a special enzyme. Identify which of the following statements does NOT provide a reason for this lack of reactivity.
A) The pka of NH₄⁺ is ∼10 and the pka of H₂O is ∼16.
B) The nitrogen of the amide can donate electrons to make a resonance structure that stabilizes the partial positive charge on the carbon.
C) −NH₂ is not as stable of a leaving group as OH, since it is less electronegative.
D) There is significant 'double-bond' character between the carbon and nitrogen in an amide.