A Level Chemistry - Solubility of Amines vs Amides

Hey, I wanted to know what the ans to that q was and why^

You see, I thought Amides would be more water soluble because it can form H bonds with water at 3 different sites, N, H and O of the C= O group whereas Amines can only have 2 sites to form H Bonds with Water (The N and H respectively). So is it possible therfore that Amides are more water soluble than amines simply because they can form more H bonds with water?

However, in terms of bacisity, amides are weaker bases than amines due to the Lonepairs of Electrons of nitrogen in Amide being less available (because of the electron withdrawing power of the Oxygen in the carbonyl group), hence they (Lp on N) become somehwat delocalised and the nitrogen is more stable (less willing to give up it's LP).
Would this effect therefore impact the LP availability of the N in an amide and thus affect it's H bonding ability in water? Hence deeming it less water soluble than amines?

But then can this explain why Amides have even higher boiling points than carboxylic acids and amines?

I know it's quite chunky, and thanks for pulling through this far!

RevLad

Quite a few different aspects here

Amides are typically less soluble than similar amines. They are perfectly fine at accepting H-bonds (usually through C=O: rather than N: due to the delocalisation you've mentioned). Numbers of H-bond donors is going to vary - Tert. amides don't have any N-H's to be H-bond donors.

So another factors is the basicity: amines are going to be much more ionised than amides are in water and this aids their solubility in a polar solvent.

In terms of boiling points it depends on the type of amide again a primary amide will form more H-bonds than a carboxylic acid as an amide will have 2 N-H donors and 2 C=O: acceptors compared to 1 O-H donor and 2 C=O: acceptors.