In our lab we tried to isolate the compounds of an equally proportioned mixture of benzoic acid: 2-naphthol: diphenyl sulfone. Benzoic acid was deprotonated by NaHCO3 and then reprotonated by HCl and 2-naphthol was deprotonated by NaOH and also reprotonated by HCl in order to extract them from the mixture.
Benzoic acid had a percent recovery of 34% and 2-naphthol had a percent recovery of 85%. Why could this be? (ex. could it be that benzoic acid is a stronger acid and therefore more dissociation occurs, losing mass?)