Solubility of Aniline and Acetanilide in aqueous HCl?

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SUMMARY

Aniline is soluble in aqueous hydrochloric acid due to the availability of its nitrogen lone pair, which can readily react with HCl to form an anilinium ion. In contrast, acetanilide is not soluble because its nitrogen lone pair is involved in resonance with the acetyl group, making it less available for protonation. This fundamental difference in electronic structure and reactivity explains the solubility disparity between these two compounds in acidic conditions.

PREREQUISITES
  • Understanding of acid-base chemistry
  • Familiarity with resonance structures
  • Knowledge of organic functional groups
  • Basic principles of solubility
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  • Research the mechanism of protonation in amines
  • Study the effects of resonance on reactivity in organic compounds
  • Explore solubility rules for organic compounds in different solvents
  • Investigate the properties of anilinium ions in aqueous solutions
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Chemistry students, organic chemists, and anyone interested in the solubility behavior of amines and their derivatives in acidic environments.

nimbuscloud
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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!
 
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nimbuscloud said:
Is that answer along the right track?

Seems like. Just explain what happens in the acid solution.
 
Thanks! I think I figured it out.
 

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