In a isolation of organic compounds phenanthrene, methyl4-aminobenzoate and 1,4-dibromobenzene was dissolved in diethylether. HCl was used to separate the aqueous and organic layer. Theaqueous layer contains methyl 4-aminobenzote +H⁺+Cl^-. 6M NaOH was added to the aqueous layer, methyl4-aminobenzote + water and NaCl was yield after the NaOH addition.This was followed by the addition of dichloromethane. After thisaddition you have two layers: one layer contains methyl4-aminobenzoate + water +dichloromethane, the other layer containswater and NaCl.

(1)Can you explain and draw the reaction that takes place whenHCl is added? Why was it necessary to add HCl?

(2)Can you explain and draw the reaction that happens when NaOHis added? why was it necessary to add NaOH?

(3) in a flask you had two layers one contained methyl4-aminobenzoate, water and dichloromethane and the other layercontained water and NaCl. How can you identify the aqueous layerfrom the organic layer. Which layer is on top and which layer is onthe bottom and why?

(4) when doing a crystallization a student is given a flask withphenanthrene, 1,4-dibromobenzene and diethyl ether. The solvent ofchoice for the crystallization is ethyal alcohol. Can you draw thereaction that takes place when ethyl alcohol is added to the flaskcontaining: phenanthrene, 1,4-dibromobenzene and diethyl ether? Whywas ethyl alcohol the solvent of choice? Do you think there is abetter solvent of choice?