Question

In: Chemistry

Identify organic and aqueous solvent layers AND Isolate and ID organic compound Possible solids: fluorene, triphenylmethanol,...

Identify organic and aqueous solvent layers AND Isolate and ID organic compound

Possible solids: fluorene, triphenylmethanol, benzoic acid, salicylic acid, ethyl-4-aminobenzoate, para-aminoacetophenone

Possible organic solvents: diethyl ether, hexane, methylene chloride

Possible aqueous layer: water, 1M NaOH, or 1M HCl

What steps can be done to do this in the lab?

Solutions

Expert Solution

You can begin by adding a little volume of hexane, the only compound that will dissolve is fluorene (the least polar compound). To the residual compounds you can add diethyl ether and all should dissolve, then add a volume of 1M NaOH, the acid compounds will be deprotonated and will dissolve into the aqueous layer and can be extracted, this are benzoic acid and the salicylic acid; to separate them you need to add 1M NaOH to obtain a neutral pH, the compounds will protonate again, and you can add ether, salicylic acid should be slightly more soluble in water than the other acid due to the presence of -OH group, benzoic acid should remain the the organic phase,note that for a good separation you need to use another technique because both acids have similar polarity.

The remaining compounds (in the initial ether phase) can be extracted adding 1M HCl, the compounds with the -NH2 group will protonate and dissolve into the aqueous phase (ethyl-4-aminobenzoate and para-aminoacetophenone), triphenylmethanol should reamain the the ether phase. The extracted aqueous phase with ethyl-4-aminobenzoate and para-aminoacetophenone can be treated with 1M NaOH to get a neutral pH and then with a volume of ether, ethyl-4-aminobenzoate will be slightly more soluble in this organic phase because an ether is les spolar than an esther, but again,both have similar polarity and the separation will not be very effective, there's necessary an additional separation technique.


Related Solutions

describe the procedure for carrying out solvent extraction from an organic layer into an aqueous layer,...
describe the procedure for carrying out solvent extraction from an organic layer into an aqueous layer, where the aqueous layer is heavier than the organic layer. Then, describe the procedure for a solvent extraction from an aqueous layer into an organic layer, where the aqueous layer is heavier than the organic. please higlight main differencces between the two procedures.
Organic chemists use many types of chromatography to separate, isolate, or identify molecules based on physical...
Organic chemists use many types of chromatography to separate, isolate, or identify molecules based on physical properties. Gas chromatography separates molecules based on which physical properties?
Part A Combustion analysis of toluene, a common organic solvent, gives 8.79 mg of CO2 and 2.06 mg of H2O. If the compound...
Part A Combustion analysis of toluene, a common organic solvent, gives 8.79 mg of CO2 and 2.06 mg of H2O. If the compound contains only carbon and hydrogen, what is its empirical formula? Express your answer as a chemical formula. Part B Menthol, the substance we can smell in mentholated cough drops, is composed of C, H, and O. A 0.1307 −mg sample of menthol is combusted, producing 0.3678 mg of CO2 and 0.1507 mg of H2O. What is the empirical formula for menthol? Express your answer as a chemical formula. Part C If the compound has a molar...
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT