While amides are much less basic than amines, they are much stronger acids. Amides have pKa values in the range 14-16, whereas for amines, pKa = 33-35.
(a) What factor accounts for the much greater acidity of amides?
(b) Imides, that is, compounds with the structure

are even stronger acids than amides.
For imides, pKa = 9-10, and as a consequence, water-insoluble imides dissolve in aqueous NaOH by forming soluble sodium salts. What extra factor accounts for the greater acidity of imides?

Transcribed Image Text:

N. R', Z-I