Chapter 14, Problem 6RAT

Alkaloids salts are not very soluble in the organic solvent diethyl ether. What might happen to

the free-base form of caffeine (an alkaloid) dissolved in diethyl ether if gaseous hydrogen chloride, $\text{HCl}$, were bubbled into the solution?

(a) A second layer of water would form.

(b) Nothing; the $\text{HCl}$ gas would merely bubble out of solution.

(c) The diethyl ether-insoluble caffeine salt would form as a white pecipitate.

(d) The acid-base reaction would release heat, which would cause the diethyl ether to start evaporating.