simplecrayola Posted October 23, 2016 Share Posted October 23, 2016 (edited) 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 Link to comment Share on other sites More sharing options...
Fuzzwood Posted October 23, 2016 Share Posted October 23, 2016 HCl is a gas. I don't see either of these solids dissolve into it. Link to comment Share on other sites More sharing options...
simplecrayola Posted October 23, 2016 Author Share Posted October 23, 2016 (edited) 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 Link to comment Share on other sites More sharing options...
John Cuthber Posted October 23, 2016 Share Posted October 23, 2016 Ignore the HCl for a minute. Consider dissolving the two organic acids in water. Link to comment Share on other sites More sharing options...
simplecrayola Posted October 24, 2016 Author Share Posted October 24, 2016 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? Link to comment Share on other sites More sharing options...
John Cuthber Posted October 24, 2016 Share Posted October 24, 2016 "soluble" and "insoluble" are not yes/ no things. How soluble are they? Link to comment Share on other sites More sharing options...
simplecrayola Posted October 24, 2016 Author Share Posted October 24, 2016 "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. Link to comment Share on other sites More sharing options...
Elite Engineer Posted October 25, 2016 Share Posted October 25, 2016 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 Link to comment Share on other sites More sharing options...
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