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Org Chem Solubility! Help!

simplecrayola
in Homework Help

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I'm trying to come up with an explanation as to why benzoic acid is insoluble in 5% HCl solution while salicylic acid is soluble in HCl. From what I've read, HCl test is used to check for the presence of basic groups. So I was thinking benzoic acid is insoluble because of the COOH group present. However, salicylic acid also has a COOH group. Is the OH group in the salicylic acid enough to make it act as a base in its reaction with HCl?

Edited by simplecrayola

HCl is a gas. I don't see either of these solids dissolve into it.

  • Author

HCl is a gas. I don't see either of these solids dissolve into it.

Sorry if it was unclear. I meant in 5% HCl solution.

Edited by simplecrayola

  • Author

I've tried. Both were insoluble in water. This is due to the benzene rings being bulky making it more nonpolar. Am I right? Or have I missed something?

  • Author

"soluble" and "insoluble" are not yes/ no things.

How soluble are they?

Benzoic acid is almost insoluble while salicylic acid is sparingly soluble in certain temperatures.

 

P. S. I'm sorry if I'm not taking the hint very quickly.

It's more to do with the solvent than the HCl in the water. Salycilic acid is soluble in water (2.48g/L @ STP). Benzoic acid is also soluble in water (3.44 g/L @ STP

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