How would one design an organic separation of a sample containing 10 grams aniso

Question

How would one design an organic separation of a sample containing 10 grams anisole (methoxybenzene), 2.0 g benzoic acid and
0.2 g fluorenone with the goal of isolating anisole and benzoic acid? Regular ogranic chemistry glassware is available.

In addition the following materials are available as well: 2.5 M NaOH, heating mantles, variacs, 3.0 M HCl ,oven @100oC, anhydrous magnesium sulfate, explosion proof hot plates, t-butyl methyl ether (maximum of 25 mL/student), stirrer, hot plates, Ethanol, thermometers, Ice, Sand, vigreux column, filter paper, regular and fluted,pH paper

Explanation / Answer

* First dissolve all the three compounds in t-butylmethylether.

* Add 2.5 M NaOH, only benzoic acid reacts with NaOH forming sodium benzoate salt and enters into aqueous layer. By filtration this can be separated. The queous layer if treated with 3.0 M HCl the benzoic acid will be regenerated and it can be filtered off.

* Now in the mixture we have anisole and fluorenone. We have the heating apparatus with. So, simply go for haeting, all the anisole willbe liquified first becuase it melting point ( - 37 degree C) is too low than fluorinone (83.5 degree C). ANd it can be separated.

Even you can also boil off the anisole (154 degree C) from fluorenone (342 degree C)

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