Suppose you have crude reaction mixture containing napthalene, benzoic acid, and aniline dissolved in an organic solvent, and you wish to extract the different molecules by altering the solubility of each component in solution. Which of the following statements would be true? a. Adding 5% HCl solution to the crude reaction mixture will deprotonate benzoic acid increasing its solubility in the aqueous solution.
b. Adding 5% NaOH solution to the crude reaction mixture will protonate napthalene making it more soluble in the aqueous solution.
c. Adding 5% HCl solution to the crude reaction mixture will protonate napthalene making it more soluble in the aqueous solution.
d. Adding 5% HCl solution to the crude reaction mixture will protonate aniline increasing its solubility in the aqueous solution.