Question

You are given a mixture of three compounds: phenanthrene (0.25 g), 1,4-dibromobenzene (0.05 g) and 4-aminoacetophenone (0.20 g). The mixture can be dissolved in either diethyl ether or methylene chloride. Write a brief separation scheme that will isolate these compounds using extraction and recrystalization techniques (you only need to separate two out of the three).

Reagents available: 1M NaOH, 6M NaOH, 1M HCl, 6M HCl, 1M NaHCO3, saturated sodium chloride, diethyl ether, 95% ethanol, methanol, isopropyl alcohol, acetone, hexane, toluene, methylene chloride, and granular anyhydrous sodium sulfate.