So I recently wrote one of the AAMC exams and got a 2/3 of a passage of organic chem wrong.
My main issue was about solubility of organic compounds in dilute acid or dilute base. What makes an organic compound dilute in either and not in water?
Any help would be great. Thanks
Organic acids and bases only become soluble in water when you can ionize them, either by deprotonating or protonating. Water is polar and likes to solvate charges, whether + or -.
The stronger organic acids, like carboxylic acids and picric acid (phenol with 3 nitro groups), are reactive to pretty much every base, so NaHCO3 and NaOH will do the trick and make them negatively charged. Once an organic molecule has any sort of discrete charge, it will become very water soluble.
Weaker acids like ammonium (NH4+), phenols, and thiols need a stronger base to deprotonate them, but the idea is the same. NaHCO3 probably won't work well but NaOH will.
Organic bases usually involve amines. To get them to be water soluble, you have to make them + charged by giving them another proton. Lots of aqueous acids can do this, like HCl, H2SO4, HBr, etc.
