Solubility of Aniline and Acetanilide in aqueous HCl?

AI Thread Summary
Aniline is soluble in aqueous hydrochloric acid due to its nitrogen atom having a lone pair that can readily accept a proton, forming 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. The discussion emphasizes the role of protonation in solubility, with aniline's structure favoring this reaction. Understanding the interaction of these compounds with acid is crucial for explaining their differing solubility. The conclusion highlights the importance of molecular structure in determining solubility in acidic solutions.
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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