Experiment 7: Solubility Classification

Festin, Aegina Joy M. WAD1, Group 7, Ma’am Noime Walican

Raquepo, Veronica V. February 8, 2014

I. ABSTRACT

Determining the solubility of an organic compound is very important key as it can provide useful
information regarding the composition of the compound. In this experiment, the solubility of each of the
thirteen samples – alanine, aniline, benzamide, benzoic acid, chlorobenzene, cyclohexane, ethylamine,
ethylacetate, hexane, α -naphtol, phenol, salicylic acid and sulfanilic acid – was evaluated using different
solvent systems. Seven solvent samples – water, 5% NaOH, 5% HCL, 5% NAHCO3, ether, concentrated
H2SO4 and 85% H3PO4, were used and the extent of dissolution of the samples were noted as +++ for
completely soluble, ++ for partially soluble, + for slightly soluble, and X for insoluble.

II. Keywords: miscibility, dissolution, solubility, solubility classification, solute, solvation, solvent

α -naphtol, phenol, salicylic acid and sulfanilic

III. INTRODUCTION acid).

The solubility of a substance pertains to the A comprehensive understanding of the

amount of a given substance that will dissolve in a
given solvent. If more than 0.1 g of that substance
dissolves in 100 mL solvent, that sample is
soluble, and if less than 0.1 g dissolves, it is
insoluble. The solute is the one to be dissolved
and the solvent is the base substance. Miscibility
is also encountered in this topic. A miscible
substance is soluble with no limits while
immiscible shares the same meaning with
insoluble.
Breaking and reintroducing attractive forces
between the solute and solvent particles is the
dissolving process also known as solvation.
Solubility in general follows the “like dissolves
like” rule wherein polar solutes dissolve in polar
solvents and nonpolar solutes dissolve in
nonpolar solvents.
There are many factors that affect the
solubility of a compound. The compound’s nature
or polarity hugely affects its solubility as well as
the temperature, molecular weight, acidity or
basicity of the compound, intermolecular forces of
attraction, structure of the compound, and
pressure.
The students must be able to identify at the
end of the experiment the solubility, and the
acidity and basicity of the different organic
compounds sampled (alanine, aniline,
benzamide, benzoic acid, chlorobenzene,
cyclohexane, ethylamine, ethylacetate, hexane,
solubility of compounds is particularly needed
when it comes to the determination of unknowns
in the laboratory. It is also fundamental not only in
many scientific disciplines but also in numerous
practical applications such as the use of
medicine, transport of pollutants, food science,
and the field of pharmaceutics.
IV. EXPERIMENTAL
5-mL test tubes were used as container
for the solutions.
The samples whose solubility will be
determined were alanine, aniline, benzamide,
benzoic acid, chlorobenzene, cyclohexane,
ethylamine, ethylacetate, hexane, α -naphtol,
phenol, salicylic acid and sulfanilic acid. The
solvent samples used were water, 5% NaOH, 5%
HCL, 5% NAHCO3, ether, concentrated H2SO4
and 85% H3PO4.
About 30 mg of each of the solid samples
were used and the solubility of each was
evaluated by adding 20 drops of the solvent.
As for the liquid samples, 2 drops of the
liquid sample were placed in respective test tubes
and 20 drops of the solvent were added.

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Chem 31.1 Solubility Classification Page 1 of 4
 V. Results
S SOLVENT SYSTEM C
A L
H2O Ether 5% 5% 5% Conc. 85%
M A the solubility in 5% sodium hydroxide solution of
P
NaOH NaHCO3 HCl H2SO4 H3PO4
S a water insoluble unknown is a strong indication
L of an acidic functional group. 3) Deductions
E S
about molecular size and composition can also
1 +++ X ++ ++ +++ X + S2
sometimes be made. For example, in many
2 X +++ X X ++ +++ ++ B homologous series of monofunctional
3 X X + + ++ +++ +++ N compounds, the members with fewer than about
4 X +++ +++ +++ X ++ X A1 five carbon atoms are water soluble, whereas
5 X +++ X X X ++ X I the higher homologs are insoluble. In these
6
tests, compounds that dissolve to the extent of
X +++ X X X +++ +++ I
about 30mg per 1 mL of the solvent are
7 ++ +++ X X X X X SB considered soluble. Some textbooks consider 33
8 X +++ X X X ++ X SN mg of solute per 1 mL of solvent as the standard.
9 X +++ ++ X X ++ ++ I Since most organic molecules have both a
10 X +++ ++ X X ++ X AW polar and a nonpolar entity, it can be deduced
that its solubility would depend on the balance
11 X +++ +++ ++ X ++ X AW between the two parts. As the percentage of the
12 + +++ +++ +++ + ++ X A1 hydrocarbon portion increases while the polar
13 + + +++ +++ + X ++ A2 part remains unchanged, the solubility in polar
Table 1. Experimental results of the solubility tests (1 – solvent decreases while that in nonpolar solvent
alanine, 2 – aniline, 3 – benzamide, 4 – benzoic acid, 5 – increases.
chlorobenzene, 6 – cyclohexane, 7 – ethylamine, 8 –
ethylacetate, 9 – hexane, 10 – α-naphtol, 11-phenol, 12- The solubility behavior of a compound can be
salicylic acid, 13 – sulfanilic acid) used to place it into one of the solubility classes,
namely S1, S2, SA, SB, A1, A2, B, MN, N and I.
The results based on the extent of dissolution Different solvents are used to identify an unknown
of each sample in different solvent systems were compound; the most common are listed below
tabulated using the following notations: +++ = with their corresponding effects on compounds.
completely soluble; ++ = partially soluble; + =
slightly soluble; and X = soluble. The solubility 1. Water
classes are detailed in Table 2 in the Appendix,
including the symbols used in Table 1. This is a polar solvent which dissolves polar
compounds. Several structural features of the
VI. Discussion unknown can be deduced if it is water-soluble. It
must be of low molar mass and will usually
The solubility of a substance is a measure of contain no more than four to five carbon atoms,
the equilibrium between the substance in its solid unless it is polyfunctional. It must contain a polar
state and the substance, or its ions, in solution. It group that will form a hydrogen bond with water,
can also be defined as the maximum amount of such as the hydroxy group of an alcohol or a
solute that can be dissolved in a fixed amount of carboxylic acid, the amino functionality of an
solvent at a specific temperature. amine, or the carbonyl group of aldehydes or
There are three kinds of information that can ketones. Esters, amides, and nitriles dissolve to a
often be obtained about an unknown substance lesser extent, and acid chlorides or anhydrides
by a study of its solubilities in water, 5% sodium react with water rather than simply dissolving in it.
hydroxide solution, 5% sodium bicarbonate On the other hand, alkanes, alkenes, alkynes,
solution, 5% hydrochloric acid solution, cold and alkyl halides are water-insoluble.
concentrated sulfuric acid and 85% H3PO4. 1) The The borderline for water solubility of
presence of a functional group can be detected. monofunctional organic compounds is most
For instance, because hydrocarbons are insoluble commonly at or near the member of the
in water, the mere fact that an unknown is homologous series containing five carbon atoms.
partially soluble in water indicates that a polar Thus, butanoic acid is soluble, pentanoic acid is
functional group is present. 2) Solubility in certain borderline, and hexanoic acid is insoluble in
solvents gives more specific information about the water.
functional groups. For example, benzoic acid is
insoluble in a polar solvent, water, but is 2. Diethyl Ether
converted by 5% sodium hydroxide solution to a
salt, sodium benzoate, which is readily water Diethyl ether is a nonpolar solvent that is
soluble. In this case, then, used to determine whether the water-soluble
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Chem 31.1 Solubility Classification Page 2 of 4
substance is extremely polar. If it is, then it cannot
be dissolved in ether. Examples are salts of
organic acids, amine hydrochlorides, amino acids
and polyfunctional compounds with hydrophilic
functional groups. If it is soluble, then it is said to
be organic because the hydrocarbon portion
interacts with ether, however small. The acidity of
those that are ether soluble is tested using litmus
paper. Compounds that turn blue litmus into red
are acidic and are most likely carboxylic acids;
those that turn red litmus paper into blue are
amines; and those that are neutral are usually
alcohols.
3. 5% Sodium Hydroxide
Compounds dissolve in aqueous base
solutions because they form sodium salts that are
soluble in aqueous medium. However, the salts of
some high molecular weight compounds are not
soluble and will precipitate out.
Both phenols and carboxylic acids produce
resonance stabilized conjugate bases. In phenols,
substitution of an electron withdrawing group
(nitro or cyano) at the ortho and para positions of
the ring increases the acidity. Phenols with two or
three nitro groups at the ortho and para positions
are strong acids that will dissolve in both strong
and weak bases.
Carboxylic acids, which are strong acids, and
phenols, which are weak acids, dissolve in
sodium hydroxide because they are converted
into their water-soluble sodium salts.
4. 5% Sodium Bicarbonate
6. Concentrated H2SO4
Concentrated sulfuric acid protonates all
organic compounds that contain oxygen and/or
nitrogen, as well as alkenes and a few aromatic
hydrocarbons. These protonated organic
compounds exist as ionic salts in sulfuric acid.
Because sulfuric acid is a highly polar liquid, it
dissolves the protonated compounds. The
dissolution of compounds in H2SO4 may also
produce large amounts of heat and/or a change in
the color of the solution. For example, an alkene
adds the elements of sulfuric acid to form an alkyl
hydrogen sulfate that is soluble in the acid, and an
oxygen-containing compound becomes protonated
in concentrated acid to form a soluble oxonium
salt. Substances that exhibit this solubility
behavior are termed “neutral” compounds.
Compounds which are insoluble in sulfuric
acid are extremely weak bases. It is the extreme
acidity of concentrated sulfuric acid along with its
powerful ionizing ability that allows these
compounds to be soluble in sulfuric acid. Thus
sulfuric acid is able to protonate alcohols, ketones
aldehydes,ester an unsaturated hydrocarbons.
The resulting ions produced are soluble in the
medium.

When a compound is insoluble in water but

soluble in NaOH, it is either a weak or a strong
acid. Testing its [unknown’s] solubility in sodium
bicarbonate (pKa=10.3), which is less basic than
sodium hydroxide (pKa=13.8) will differentiate
strong acids from weak acids. Strong acids can
easily be deprotonated and can attack even a
weak base such as sodium bicarbonate, so they
are soluble in this solvent. Weak acids, unlike the
strong ones, do not react with weak bases. Ionizing power of conc. H2SO4
5. 5 % HCl

If the compound is soluble in HCl but

7. 85% Phosporic Acid
insoluble in water, an amine should be considered
immediately. Aliphatic amines (RNH2, R2NH, Phosphoric acid, on the other hand is not
R3N) are basic compounds which readily dissolve nearly as strong an ionizing solvent as is sulfuric
in acid because they form hydrochloride salts that acid. It is capable of ionizing most of the oxygen
are soluble in aqueous medium. containing compounds such as

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Chem 31.1 Solubility Classification Page 3 of 4
alcohols,aldehydes, and esters, but is not able to
ionize unsaturated hydrocarbons such as
alkenes,alkynes or aromatics. Thus these
compounds will be insoluble in this medium.

VII. Conclusion and Recommendations

The solubility behavior of a compound is
affected by the nature of solvent. This very idea is
used to identify the structure of an unknown
compound among other tests. The solubility of an
organic compound in water, dilute acid, or dilute
base can provide useful, but not definitive,
information about the presence or absence of
certain functional groups. In reality, however, the
assignment of an unknown to a formal solubility
class may be arbitrary because a large number of
compounds exhibit borderline behavior. Table 2. Organic compounds comprising the solubility classes

It is often possible to predict the solubility

class of a particular compound solely by IX. References:
reference to its structural formula, there are many
cases where this would result in an incorrect Chemistry Online. (n.d.). Solubility. Retrieved
prediction. March 9, 2013 from
Upon shaking, when two colorless liquid
http://webapps.utsc.utoronto.ca/chemistryo
phases lie one above the other, it is often possible nline/solubility.php
to overlook the boundary between them and thus
to see only one phase. This mistake can generally Clayden J. (2001). Organic Chemistry. Oxford
be avoided by shaking the test tube vigorously University Press
when a liquid unknown seems to have dissolved
in the solvent. If two phases are present, the Gilbert, J. (2011).Experimental Organic
solution will become cloudy. Chemistry: A Miniscale and Microscale Approach.
Boston, MA: Cengage Learning
VIII. Appendix

Lehman, J. (2008) Operational Organic

Chemistry: A Problem-Solving Approach to the
Laboratory Course. Prentice Hall

Shriner, R. (2004). The Systematic Identification

of Organic Compounds. Canada: John Wiley &
Sons.

I hereby certify that I have given

substantial contribution to this report.

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Figure 1. Classification of organic compounds by solubility Festin, Aegina Joy M.

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Raquepo, Veronica V.

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Chem 31.1 Solubility Classification Page 4 of 4