Solubility of Aniline and Acetanilide in aqueous HCl?

In summary, the solubility of aniline in aqueous HCl is around 6.5 grams per 100 milliliters of water at room temperature. This is significantly lower than the solubility of acetanilide in aqueous HCl, which is around 40 grams per 100 milliliters of water at room temperature. The solubility of both compounds is affected by factors such as temperature, pH, and acid concentration. Aniline is more soluble in aqueous HCl due to its ability to react with the acid and form a more soluble salt. The molecular structures of aniline and acetanilide, specifically the presence of functional groups, also play a role in their solubility in aque
  • #1
nimbuscloud
4
0
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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  • #2
nimbuscloud said:
Is that answer along the right track?

Seems like. Just explain what happens in the acid solution.
 
  • #3
Thanks! I think I figured it out.
 

Related to Solubility of Aniline and Acetanilide in aqueous HCl?

1. What is the solubility of aniline in aqueous HCl?

The solubility of aniline in aqueous HCl is around 6.5 grams per 100 milliliters of water at room temperature.

2. How does the solubility of aniline compare to that of acetanilide in aqueous HCl?

The solubility of acetanilide in aqueous HCl is significantly higher than that of aniline, with a solubility of around 40 grams per 100 milliliters of water at room temperature.

3. What factors affect the solubility of aniline and acetanilide in aqueous HCl?

The solubility of both aniline and acetanilide in aqueous HCl is affected by temperature, pH, and the concentration of the acid. Higher temperatures and lower pH levels tend to increase solubility, while higher concentrations of the acid can decrease solubility.

4. Why is aniline more soluble in aqueous HCl than in pure water?

Aniline is a weak base, meaning it can react with acids to form salts. In aqueous HCl, aniline reacts with the acid to form aniline hydrochloride, which is more soluble in water than aniline itself.

5. How does the solubility of aniline and acetanilide in aqueous HCl relate to their molecular structures?

The molecular structure of a compound can have a significant impact on its solubility. In the case of aniline and acetanilide, the presence of functional groups such as an amine and an amide, respectively, can affect the interactions with the aqueous HCl solution and thus affect their solubility.

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