I have a mixture containing the following three compounds: 0.20g o-toluic acid,

Question

I have a mixture containing the following three compounds: 0.20g o-toluic acid, 0.25g fluorene, 0.05g of 1,4-dibromobenzene. I'm required to separate (any) two of of the three. Please could some one help me with how I'd separate two of the three above named compounds.

JUST FOR CLARIFICATION - I only have the chemicals listed below to isolate two of the above mentioned compounds and we can only use crystallization and extraction to do so,
Chemicals available for extractions: CH2CL2, 1M NaOH, 1M HCL and sodium sulfate for drying
Chemicals available for crystallization: ethyl ether, 95% ethanol, methanol, isopropyl alcohol, acetone, hexane, toluene and methylene chloride.
Thanks in advance!
Chemistry I have a mixture containing the following three compounds: 0.20g o-toluic acid, 0.25g fluorene, 0.05g of 1,4-dibromobenzene. I'm required to separate (any) two of of the three. Please could some one help me with how I'd separate two of the three above named compounds.

JUST FOR CLARIFICATION - I only have the chemicals listed below to isolate two of the above mentioned compounds and we can only use crystallization and extraction to do so,
Chemicals available for extractions: CH2CL2, 1M NaOH, 1M HCL and sodium sulfate for drying
Chemicals available for crystallization: ethyl ether, 95% ethanol, methanol, isopropyl alcohol, acetone, hexane, toluene and methylene chloride.
Thanks in advance!
I have a mixture containing the following three compounds: 0.20g o-toluic acid, 0.25g fluorene, 0.05g of 1,4-dibromobenzene. I'm required to separate (any) two of of the three. Please could some one help me with how I'd separate two of the three above named compounds.

JUST FOR CLARIFICATION - I only have the chemicals listed below to isolate two of the above mentioned compounds and we can only use crystallization and extraction to do so,
Chemicals available for extractions: CH2CL2, 1M NaOH, 1M HCL and sodium sulfate for drying
Chemicals available for crystallization: ethyl ether, 95% ethanol, methanol, isopropyl alcohol, acetone, hexane, toluene and methylene chloride.
Thanks in advance!
Chemistry

Explanation / Answer

Polarity wise fluorene will be the least polar and o-toluic acid is the highest. Hence, you can separate these two polarity differing compounds by using TLC or column chromatography. Choose proper solvent system (may be ethanol+hexane) for the separation purpose.

In column chromatography, first use very less polar solventsystem (you may use only hexane also) for separating out fluorene and then use a higher polar solvent system to separate out o-toluic acid present in the mixture. (Make sure you check TLC for separation of the spots of the compounds before going for column chromatography).

For extraction purpose, depending upon the compound to separate. If the compound to be extracted is plar then it will remian in the aqoueus layer else it will go to the organic layer. Before going for crystalization, use NaSO4 for removing water from the solution of compound in organic solvents. Further, for crystallization use the solvent in which your compound is not dissolved so as to ensure no loss of compound; the purpose of the solvent in crystallization is only to dissolve the impurities and separate them out.

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