This is the mixture I am given: 50% fluorenone, 40% benzoic acid, 10% 1,4-dibrom

Question

This is the mixture I am given: 50% fluorenone, 40% benzoic acid, 10% 1,4-dibromobenzene The goal is to isolate and purify the major components (50% and 40% components). The following reagents will be available: 1M NaOH, 6M NaOH, 1M HCl, 6M HCl, 1M NaHCO3, saturated sodium chloride, methyl t-butyl ether, ethanol, methanol, isopropyl alcohol, acetone, hexane, toluene, methylene chloride, and anhydrous sodium sulfate. Please outline how you would separate, isolate and purify the mixture above with the given reagents ---------------------- 700 points! i'll give 5 stars for effort

Explanation / Answer

Let's recall that like dissolves like and we will use this principle to separate these three compounds. first we will take the mixture in toluene only 1,4-dibromobenzen will go into hexane; fluorenone and benzoic acid being polar compound will not dissolve into hexane and thus can be filtered and the solid (containing fluorenone and benzoic acid) is washed by toluene to remove trace of 1,4-dibromobenzene. ------------ The solid mixture of fluorenone and benzoic acid is washed with acetone (fluorenone is also a ketone) and therefore will go with acetone and only benzoic acid will remain over filter paper. the filtrate is concentrated on rotavapor to get pure fluorenone-------- Now take the solid remaining on filter paper and put it into aqueous 1M NaOH and filter the solution to remove impurity if any. Now acidify (till you reach neutral solution check with pH paper) the basic solution of benzoic acid (contains sodium benzoate) with 1M HCl to get the percipitate of benzoic acid.

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