A student must choose either water or dichloromethane (CH2Cl2) to dissolve a sample of salicylic acid, whose structure contains both a benzene ring and adjacent –OH and –COOH groups. Based on intermolecular interactions, in which solvent is salicylic acid expected to be more soluble, and why?
a) Water, because the –OH and –COOH groups can engage in extensive hydrogen bonding and possible acid–base interactions with the solvent.
b) Dichloromethane, because its chlorinated solvent molecules can form stronger hydrogen bonds than water.
c) Water, because the carboxylic acid group will ionize completely, making the molecule ionic and highly soluble in the polar solvent.
d) Dichloromethane, because the polar functional groups of salicylic acid are shielded by the solvent’s non-polar region.