1. The problem statement, all variables and given/known data http://img114.imageshack.us/img114/3643/acidspicem4.th.jpg [Broken]http://g.imageshack.us/thpix.php [Broken] My book says that if I attach an electron-donating group to an acid, it would decrease the acidity of that acid because the electrons would cause the already negative ion to be more unstable. Well, -OH is an electron-donating group. I don't understand why when I attach an -OH group to acetic acid to make it into 2-hydroxyacetic acid, its acidity actually increases. It is suppose to decrease, according to the book. Does anybody know how to resolve this conflict? Also, if I compare phosphoric acid with carboxylic acid, the phosphoric acid is a lot stronger than carboxylic acid. I don't understand why. If I deprotonate 1 acid, the negative charge would form resonance with one other oxygen on both acids (phosphoric acid and carboxylic acid). I know phosphoric acid has 4 oxygens attached, but two of them would probably not be involved in resonance stabilization because they are too busy bonding to Phosphorus and Hydrogen. So, if both phosphoric acid and carboxylic acid can only form 2 resonance structures when 1 H is deprotonated, then why is phosphoric acid so much stronger than carboxylic acid? Thanks in advance.