While amides are much less basic than amines, they are much stronger acids. Amides have pKa values...

Question

While amides are much less basic than amines, they are much stronger acids. Amides have pK_a values in the range

14–16, whereas for amines, pK_a= 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, pK_a = 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?

David · Accepted Answer

AH A + H
Ka =
A H
AH
=
A H
AH
pKa = -logKa -log
So pKa more means dissociation equilibria is on the left  while pKa 
less means dissociation equilibria is on the right
So if A- is extra stabilized the equlibrium will be right side and pKa 
will be less.

While amides are much less basic than amines, they are much stronger acids. Amides have p K a values in the range 14–16, whereas for amines, p K a = 33–35. (a) What factor accounts for the much...

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