Download The results of parts A

The results of parts A - C of this experiment are consistent with the concept of polar solutes being
soluble in polar solvents and nonpolar solutes being soluble in nonpolar solvents. Benzophenone, which
is largely nonpolar, but possesses a polar carbonyl group, was found to be partially soluble in methyl
alcohol and hexane but insoluble in water. Malonic acid, a polar molecule that is also able to ionize, was
found to be soluble in water and methyl alcohol but insoluble in hexane. Finally biphenyl, a very
nonpolar molecule, was found to be soluble in hexane but insoluble in water and methyl alcohol.
In part B it was found that 1-octanol was soluble in hexane but insoluble in water. 1-butanol was
partially soluble in hexane and water. Methyl alcohol was soluble in water and partially soluble in
hexane. This demonstrates that despite having a polar hydroxyl group that can form hydrogen bonds,
alcohols become less soluble in water (and more soluble in nonpolar solvents) as the alkyl portion of the
alcohol becomes larger.
In part C, the pairs of water/ethyl alcohol and hexane/methylene chloride, were found to be miscible,
while water/diethyl ether, water/methylene chloride and water/hexane were all found to be immiscible.
The final part of this experiment was to investigate the solubility of an organic acid (benzoic acid) and an
organic base (ethyl 4-aminobenzoate) at different pH values. Benzoic acid was found to be soluble in
water and 1.0 M NaOH, however upon addition of 6.0 M HCl to this solution, benzoic acid became
insoluble. Benzoic acid was also insoluble in 1.0 M HCl. Ethyl 4-aminobenzoate was found to be insoluble
in water and 1.0 M NaOH, but upon addition of 6.0 M NaOH to this solution, ethyl 4-aminobenzoate
became insoluble. Ethyl 4-amino benzoate was also soluble in 1.0 M HCl. The results of this experiment
demonstrate that both the acid and base become more soluble when they are ionized and less soluble
when they are not.