Org Chem Solubility! Help!

[simplecrayola]

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 October 23, 2016 by simplecrayola

[Fuzzwood]

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

[simplecrayola]

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 October 23, 2016 by simplecrayola

[John Cuthber]

Ignore the HCl for a minute.

Consider dissolving the two organic acids in water.

[simplecrayola]

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?

[John Cuthber]

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

How soluble are they?

[simplecrayola]

"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.

[Elite Engineer]

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