Question

Explain the following: Ethanamide (CH₃CONH₂) is a weaker base than ethanamine (CH₃CH₂NH₂).

Answer 1

lone pair of electrons on nitrogen interacts with oxygen atom due to resonance as shown below:



Hence, the lone pair of electrons on nitrogen is less available for donation, which makes it less basic. While such mechanisms are not present in CH3CH2NH2.