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.

d. Adding 5% HCl solution to the crude reaction mixture will protonate aniline increasing its solubility in the aqueous solution.

Explanation:

On this case, we have to check the structures of each compound (figure 1). For naphthalene we dont have any functional groups therefore, the addition of HCl or NaOH it will not affect naphthalene so we can discard "B" and"C".

When we add HCl solution we will have the production the presence of this hydronium ion will protonate the acid, so we can discard a.

Finally, for d when we add the hydronium ion will react with aniline (a base) and will produce an ammonium ion. This ammonium ion have a positive charge, therefore the polarity will increase and the molecule would be more soluble on water (figure 2).

I hope it helps!

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i think the answer is terrae but not 100 percent sure. ▓▬▬ §