Given a mixture of caffeine and benzoic acid, what would happen if they were added to a separatory funnel with DCM and 1M HCl? Which compound goes into which layer and why?
a) Caffeine in organic layer, benzoic acid in aqueous layer; protonation of benzoic acid
b) Caffeine in aqueous layer, benzoic acid in organic layer; deprotonation of caffeine
c) Both compounds in organic layer; neutralization of both
d) Both compounds in aqueous layer; protonation of caffeine