1. During an extraction experiment, a student lost track of which layer was the organic layer. How could the student figure that out?
2. A mixture of compounds below is dissolved in diethyl ether and transferred to a separatory funnel. Excess 10% HCl is added and the contents of the funnel are mixed.
pentanoic acid naphthalene isobutylamine
a. When the layers separate, what compound(s) are found in the top layer? Briefly, explain your answer.
b. When the layers separate, what compound(s) are found in the bottom layer? Clearly explain your answer (write chemical equations).
c. What will be happen if you switch HCl for 5% NaHCO₃? Clearly explain your answer (write chemical equations).