Organic Chemistry Laboratory Manual 1

EXPERIMENT 1. SOLUBILITY OF ORGANIC COMPOUNDS

The solubility of an organic compound is dependent on its molecular structure. The

schematic diagram shown below gives a detailed procedure on how organic compounds can be
differentiated based on their behavior in different solvents (Scheme 1). Solubility information
gathered from this prescribed method can be used to classify an unknown organic compound
according to its main functional group.

organic compound
organic compound
+HO 2

soluble insoluble

+ diethyl ether + 5.0% NaOH

soluble insoluble insoluble soluble

S1 S2 + 5.0% HCl + 5.0% NaHCO3

water-soluble compounds
insoluble soluble

A2 A1
acidic compounds

insoluble soluble

B
basic compounds

w/ N or S

M + conc. H2SO4
miscellaneous neutral compounds
insoluble soluble

I N
inert compounds neutral compounds

Scheme 1. Solubility Classes of Organic Compounds

Solubility in water and diethyl ether

In general, if the ratio of the polar groups to the number of carbon atoms is less than or
equal to 1:5, the compound is soluble in water. Otherwise, the compound is usually insoluble or
sparingly soluble in water.

Organic Chemistry Group ● Institute of Chemistry ● University of the Philippines Diliman

Organic Chemistry Laboratory Manual 2

Branching of the alkyl group causes a decrease in the intermolecular forces of attraction
between the molecules and thus an increase in its solubility in water. Water-soluble compounds
can be further differentiated using a less polar solvent such as diethyl ether. Compounds that
are highly polar are soluble in water but insoluble in diethyl ether.

Solubility in Acids and Bases

Compounds that are soluble in 5.0% sodium hydroxide (NaOH) are acidic. This solubility
in 5.0% NaOH involves an acid-base neutralization reaction.

Sodium bicarbonate (NaHCO3), a weaker base than NaOH, can be used to determine
whether a compound is a strong or weak acid. Weak acids do not react significantly with a weak
base. Thus, compounds that are soluble in 5.0% NaOH but are not soluble in 5.0% NaHCO3 are
weak acids.

Compounds that are soluble in 5.0% hydrochloric acid (HCl) are basic compounds. The
dissolution process is mainly due to the acid-base neutralization reaction, which produces
soluble organic salts.

Solubility in Concentrated Sulfuric Acid (H2SO4)

Compounds that are insoluble in 5.0% HCl and contain nitrogen or sulfur atom are
classified as “miscellaneous neutral”. Compounds that are insoluble in 5.0% HCl but are soluble
in concentrated H2SO4 are neutral compounds. Almost all compounds containing oxygen,
nitrogen, or sulfur are easily protonated by concentrated H2SO4.

Compounds that are insoluble in both 5.0% HCl and concentrated H2SO4 are considered
inert.

In this experiment, the solubility class of different organic compounds will be determined
using the different solvent systems discussed above.

MATERIALS AND APPARATUS

Test Compounds:

acetone
aniline hexane
benzaldehyde phenol
benzamide sucrose
benzoic acid

Solvents:

distilled water 5.0% NaHCO3

diethyl ether (CH3OCH3) 5.0% HCl
5.0% NaOH concentrated H2SO4

Organic Chemistry Group ● Institute of Chemistry ● University of the Philippines Diliman

Organic Chemistry Laboratory Manual 3

Other Materials:

micro test tubes

Pasteur pipette
spatula

PROCEDURE

Use the diagram in Scheme 1 to determine the solubility class of the test compounds.

Place 5 drops of the solvent in a micro test tube. Add a pinch of the solid or 2 drops of
the liquid test compound. Shake the mixture vigorously. Use a fresh sample of the test
compound for every solvent.

A compound that is soluble in water is soluble in other aqueous solutions. For a solid
compound to be considered water-soluble it must be dissolved completely in water. In other
solvents, if the amount of solid decreases, a positive result is considered.

For a liquid test compound, the formation of a homogeneous solution is a positive result.
This means that the test compound is miscible with the particular solvent. If uncertain about
presence of layers, add one or two more drops of the liquid test compound.

WASTE DISPOSAL

1. Dilute all aqueous solutions and pour into the sink with running water. Dispose
undissolved solids in the container marked “SOLID WASTE”.

2. For heterogeneous solution, separate the two layers using a separatory funnel. Pour the
aqueous layer into the sink with running water. The organic layer should be poured into
the assigned organic waste jar.

REFERENCE

Fieser, L.F.; Williamson, K.L. Organic Experiments, 7th ed. D.C. Heath: Massachusetts, 1992; pp
573-575.

Organic Chemistry Group ● Institute of Chemistry ● University of the Philippines Diliman