Solubility of Aniline and Acetanilide in aqueous HCl?

nimbuscloud

Hi Everyone!
Hopefully someone can help me out with this question....Why is aniline soluble in aqueous hydrochloric acid, but acetanilide is not?

Is it because aniline has a lone pair on the nitrogen that is more available to react? The lone pairs in acetanilide are too tied up with resonance? Is that answer along the right track? Any help with this would be appreciated!
Thank you!

Borek

Seems like. Just explain what happens in the acid solution.

nimbuscloud

Thanks! I think I figured it out.