CHEM 31.

1: ORGANIC CHEMISTRY LABORATORY

EXPERIMENT No. 1: Solubility as a Physical Property

Materials Needed:
 250 ml Erlenmeyer flask
 12 Test tubes (6 small, 6 large)
 Bunsen burner or hot water bath set up (hot plate and beaker)
 Test tube tongs
 Stir rod
CAUTION: Organic solvents are flammable and generally toxic. Stay away from an open flame when
working with them, and avoid inhaling their vapors.
Procedure
A. Preliminary Observations of the Dissolution Process
Drop a small crystal of potassium permanganate into about 50 mL of water contained in a
250-mL Erlenmeyer flask that is placed on a white background. Observe what happens.
B. Solubility in Organic Solvent at Room Temperature
Before doing this part, record the descriptions of the pure organic compounds.
Place 2.0 mL of petroleum ether in a small, clean, dry test tube. Add the organic compound
(about 60 mg), and mix by thorough agitation. Examine the mixture carefully and record its
description.
Using the above procedure, test the solubility of each of the following organic compounds.
Set A: acetic acid, benzoic acid, sodium benzoate
Set B: cyclohexanol, dextrose, cellulose (cotton fiber)
C. Solubility in Water at Room Temperature
Adapt the procedure given in the preceding section using water in place of the organic
solvent. Test the same set of compounds for their solubility in water at room temperature. Save the
test tube containing benzoic acid-water mixture for part D).
D. Effect of Temperature on Solubility
Carefully without any spillage, pour the contents of the test tube containing the benzoic
acid-water mixture into a large test tube. Use 1.5 mL extra water to rinse out any solids adhering to
the walls of the small test tube into the larger one. The resulting mixture now contains a larger
portion of water. Is it enough to dissolve all the benzoic acid? If not, heat the test tube over a small
flame or in a water bath. Observe what happens to the mixture. When all the solids have
disappeared, remove the test tube from the heat and allow it to cool slowly. Observe what happens.
E. Effect of pH on Solubility
Using the procedure in part B, determine the solubility of the following compounds in the
following solvents: water, 10% HCl, 10% NaOH, and 10% NaHCO3.
Set C: aniline, diethylamine, naphthalene
 Set D: benzoic acid, phenol, toluene
F. Salting Out and its Effects
Add 10 drops of 1-butanol to 4 mL water in a large, clean test tube, and mix thoroughly. If
any butanol remains undissolved, add a few drops of water and agitate the mixture until finally a
true solution is observed. Record its appearance. Now, add a spatula (0.5 g) of sodium chloride
and agitate the contents of the test tube until the solids are completely dissolved. Is there any
difference between this mixture and the original solution? If no difference is observed, add more
sodium chloride and shake as before. Allow the mixture to stand for a while and repeat the
examination. Record the appearance of the new mixture.