Experiment No.

SOLUBILITY BEHAVIOR OF ORGANIC COMPOUNDS

Meremilla, A.C., Muyot,M.L., Osita, E.J., Regacho, G.
College of Science
University of the Philippines Baguio
Abstract
Solubility is defined by the quantity of solute that can be dissolved in a solvent at a certain temperature
and is an important factor in identifying the composition of a solute and solvent in a solution. Thirteen
solutes, namely hexane, benzamide, acetone, ethyl alcohol, benzyl alcohol, aniline, toluene, sucrose,
benzaldehyde, benzoic acid and phenol, were tested for their solubility with six different solvents, distilled
water, ether, 5% NaHCO3, 5% NaOH, 5% HCl and Conc. H2SO4, and was classified either (+) soluble or
(-) insoluble. In the experiment that was conducted, only three solutes, acetone, ethyl alcohol and
sucrose, were soluble to water. It infers that the hydrogen bonds present in the solvent and the dipoledipole interaction in the polar solute molecules were supplanted by the hydrogen bonding between the
solutes and solvent. Therefore, the researchers concluded that the intermolecular forces of attraction
were responsible for the solubility of compounds in a solvent and thus, it can be used in identifying the
structure of a given compound. An organic compound's solubility in water, dilute acid or dilute base can
be used to identify, but not define, the functional groups present.

Introduction
Solubility of a substance is defined by the maximum quantity of solute that can be dissolved in a
solvent at a certain temperature. A mixture of a solute and solvent is called a solution. Soluble and
insoluble are the terms used for the solubility of a solid with a liquid. But when it comes to the solubility of
both liquid compounds, the terms used are miscible and immiscible. Substances that can be dissolved
100% are called soluble or miscible and those that cannot be dissolved 100% are called insoluble or
immiscible. There are some factors that affect the solubility of a substance, namely, forces between
particles, pressure, and temperature. Compounds that have similar properties are mostly soluble in each
other and compounds that have different properties are mostly insoluble in each other. The rule of like
dissolves like is being applied. One example is polar to polar compounds and non-polar to non-polar
compounds.
At the molecular level, solubility is controlled by the energy balance of intermolecular forces
between solute-solute, solvent-solvent and solute-solvent molecules. Based on the solubility of a solute,
the possible results are, if the solution has less solute than the maximum amount that it is able to
dissolve, it is a dilute solution; if the amount of solute is exactly the same amount as its solubility, it is
saturated, and if there is more solute than is able to be dissolved, the excess solutes separates from the
solution.
Knowing the solubility of compounds is important because the solvent choice can determine the
possible yield of the reaction. It can also be used in looking at the relationships between solubility
properties of an organic molecule and its structure. By knowing the structure of a molecule, its function
can be predicted, such as its solubility, acidity, or basicity, stability, reactivity, etc.
This experiment aims to know the solubility of the compounds, hexane, benzamide, acetone,
ethyl alcohol, benzyl alcohol, aniline, toluene, sucrose, benzaldehyde, benzoic acid, and phenol. It also
aims to classify each compound into water soluble, ether-soluble, strong acid, weak acid, base, neutral,
miscellaneous neutral, or inert. Determination of their intermolecular forces of attraction and the chemical
reactions involved are also included.

Results and Discussion

Solubility can be defined as the maximum amount of solute that can be dissolved in a fixed
amount of solvent at a specific temperature. The polarity of the molecules determines the forces of
attraction between the molecules in the liquid state. These intermolecular forces which exist between
molecules determine the functions of a compound: its acidity, basicity, stability and reactivity. These forces
of attraction depend on the structure and the functional groups present in a molecule.
The table below summarizes the results of the experiment:
Solutes

Water

Ether
+
+
n/a
n/a
n/a

5%
NaOH
n/a
n/a
n/a
+
+
-

5%
NaHCO3
n/a
n/a
n/a
+
n/a

5%
HCl
n/a
n/a
n/a
n/a
n/a
+

Concentrated
H2SO4
n/a
n/a
n/a
n/a
n/a
n/a

Classification
of solute
S1
S1
S2
A1
A2
B

Acetone
Ethyl alcohol
Sucrose
Benzoic acid
Phenol
Aniline

+
+
+
-

Benzaldehyd
e
Benzy
alcohol
Hexane
Toluene

n/a

n/a

++

n/a

n/a

++

n/a
n/a

n/a
n/a

I
I

Table 1: Summary of the results obtained after the experiment

Water Soluble Compounds

As obtained in the first step, water-soluble compounds include Acetone, Ethyl alcohol, and
Sucrose. Other compounds did not form homogenous solution with water hence they are not considered
to be soluble in water. Below are the compounds acetone, ethyl alcohol, and sucrose showing the
functional groups present in their structure:

Figure 1. Chemical structure of Acetone

Figure 2. Chemical structure of Ethyl alcohol

Figure 3.Chemical Structure of Sucrose

The main functional group in acetone or propanone is ketone with the structure RC(=O)R'. These
compounds contain a carbon-oxygen double bond known as a carbonyl group. On the other hand, ethyl

alcohol or ethanol is an alcohol in which the hydroxyl functional group (OH) is bound to a saturated
carbon atom. Sucrose contains both hydroxyl and ether groups in its structure. An ether contains an
oxygen atom bonded to two alkyl or aryl group and is of the general formula ROR'.
Compounds containing carbonyl or hydroxyl groups are considered polar due to the presence of
an electronegative atom in their structure, meaning they have a slightly positive side and a slightly
negative side. As a rule of thumb, like dissolves like. Water is a polar molecule thus it can dissolve polar
compounds. These compounds simply dissolve in water rather than reacting with it. A special type of
dipole-dipole force known as Hydrogen bonding exists between the solutes used and the water solvent.
One of the slightly positive hydrogen atoms in the water molecule is sufficiently attracted to one of the
partially negative-charged Oxygen atom of the solute. However, unlike in alcohols, ketones dont have
any hydrogen atoms attached directly to the oxygen, and so they do not form hydrogen bond with each
other.
Moreover not all groups with carbonyl or hydroxyl groups are soluble in water. Take for example,
benzoic acid and benzyl alcohol. Compounds must be of low molar mass and it should contain no more
than four to five carbon atoms, unless it is polyfunctional. For monofunctional organic compounds, the
borderline for water solubility is five Carbon atoms. This means that compounds having five Carbon
atoms may or may not be soluble in water and compounds that exceed five Carbon atoms is insoluble in
water.

Ether Soluble Compounds

For the ether solubility test, only compounds acetone and ethyl alcohol yield a positive result.
Sucrose did not dissolve in diethyl ether thus it is an extremely polar compound.
Ethers are polar solvent but not as polar as other functional groups, this is the reason why it
cannot dissolve salts of organic acids, amine hydrochlorides, amino acids and polyfunctional compounds
that consist hydrophilic functional groups.
Sucrose, being made up of two simple sugar molecules namely, Glucose and Fructose, and the
presence of carbonyl groups on its structure, becomes an extremely polar compound, thus, making it
insoluble with a slightly polar solvent. Without water as a solvent, the sugar molecules cannot be broken
because of their tight hydrogen bond.
Organic Acid Compounds
5% NaOH was added to water-insoluble compounds to test which of these are acidic. Any
substance that was soluble in strong base, such as 5% NaOH is considered an acid, either be strong or
weak organic acid because it converts into water-soluble sodium salts. When this solvent was added,
only compounds Benzoic acid and Phenol were dissolved.
Reaction of Benzoic acid with sodium hydroxide yields produce water and sodium benzoate, which is an
ionic compound:

Figure 4. Chemical reaction for the addition of Benzoic acid to Sodium Hydroxide yielding Sodium benzoate and water

The acidic portion of benzoic acid is the carboxyl group. Carboxylic acids exist primarily in their ionic,
conjugate base form when subjected in an adequate basic environment
Phenol reacts with sodium hydroxide solution to give a colourless solution containing sodium phenoxide:

Figure 5. Chemical reaction of Phenol with Sodium hydroxide yielding Sodium phenoxide and water.

In this reaction, the hydrogen ion has been removed by the strongly basic hydroxide ion in the sodium
hydroxide solution.
Ion-dipole forces exist in these compounds. Ion-dipole forces were generated between polar
water molecules and a sodium ion. The oxygen atom in the water molecule has a slight negative charge
and is attracted to the positive sodium ion. These intermolecular ion-dipole forces are stronger than dipole
interactions because the charge of any ion is much greater than the charge of a dipole. Ion-dipole
bonding is also stronger than hydrogen bonding.
Strong Organic Acid Compounds

Further addition of a weak base such as 5% NaHCO 3 determines whether the acid is strong or
weak. If the solute is soluble in a weak base such as the said solvent, then it is a strong organic acid.
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.
Benzoic acid is the only solute that was observed to be soluble in both 5% NaOH and 5% NaHCO3.
Thus, carboxylic acids are strong organic acids.

++ H 2 C O3
N a
C6 H 5 COOH + NaHC O3 C 6 H 5 CO O
Balanced chemical equation of the addition of NaHCO3 to Benzoic acid

Weak Organic Acid Compounds

Weak acids, unlike the strong acids, do not react with weak bases like sodium bicarbonate
but is soluble in strong base. In the experiment, phenol, a compound that has an OH attached to a
benzene ring is the weak acid.
Phenol is a large organic molecule with a little non polar group. It produces resonance stabilized
conjugate bases on its benzene ring. These conjugated electrons in the benzene ring pull electrons away
from the OH group. The electron pair of O-H bond is withdrawn more towards O and H+ ion can be easily
released in aqueous solution. Sodium Bicarbonate is a weak base so it easily accepts protons from a
stronger acid such but it is not strong enough to pull the proton of the phenol thus it does not create a
reaction with the phenol group.
Compounds which are insoluble in 5% NaOH but are soluble in 5% HCl are known as basic
compounds. In this experiment, aniline, or phenylamine is the only compound identified as a base (B). A
base, defined by Lewis, is any substance that can donate a pair of nonbonding electrons (an electron pair
donor)
Aniline is classified under the functional group of amines, which are identified as bases due to the
lone pair of electrons in the nitrogen accepting hydrogen. Aniline, an aromatic amine, is slightly, but not
completely soluble in water because it can form hydrogen bonds. Its incapability to get completely

dissolved in water is because of the compounds benzene rings which break off these hydrogen bonds,
and because the water molecules involved here interrupt the van der Waals attractions between the
aniline molecules. (Clark, 2004)

Figure 3.Chemical Structure of Aniline

Aniline, a weak base an, is not as strong as a base as other amines. This is due to nitrogen being
delocalised with the lone pair of electrons, thereby causing it to have a less intense capacity to combine
with the hydrogen atoms. Reacting with 5% HCl, a strong acid, aniline dissolves completely and forms a
salt solution known as phenylammonium chloride.
C6H5NH2(aq) + HCl -> C6H5NH3+(aq) ClC6H5NH2(aq) + H+(aq) C6H5NH3+(aq)

Benzamide has been identified as a miscellaneous neutral compound (M) because it had been
insoluble in water and NaOH, and its solubility in HCl was unidentifiable. Miscellaneous neutral
compounds contain nitrogen or sulfur atoms and undergo hydrolysis and reduction when heated.

Figure 4.Chemical Structure of Benzamide

Benzamide, C6H5CONH2, is an amide derived from benzoic acid. It is slightly soluble in water and
hydrolyzes to form carboxylic acid and an amine under the presence of a strong acid. In this case, the
strong acid used was HCl and its reaction with benzamide (and NaOH) yielded sodium benzoate and
ammonia.
C6H5CONH2 + HCl + NaOH -> NaCHO + NH3
Benzyl alcohol and benzaldehyde have been identified as neutral compounds (N) because they
had been insoluble in water, NaOH, and HCl, but soluble in concentrated H 2SO4. Neutral compounds are
unsaturated and contain oxygen. Examples of functional groups under this include alcohols, aldehydes,
anhydrides, esters, ethers, and ketones (McMurry, 2008). Concentrated H 2SO4 is highly polar and is
capable of protonating all organic compounds containing oxygen and/or nitrogen, which then exist as
ionic salts. Compounds reacting with H 2SO4 exhibit properties of chemical change, such as heat
production, evolution of gas, or color change.
Benzyl alcohol is a primary alcohol w/ an arene group. It is very polar and cannot dissolve in
water, like all alcohols which are "protic" solvents (with a hydrogen atom attached to an oxygen atom.)

Alcohols undergoes what is known as a dehydration reaction, in where the elimination of water molecule
replaced by a pi bond between carbon atoms, forming alkenes when heated with strong acids.

Figure 5.Chemical Structure of Benzyl Alcohol

Primary and secondary alcohols can be oxidized to aldehydes and ketones. Benzyl alcohols
reaction with sulfuric acid (sulfonation) is shown below:
C6H5CH2OH(aq) + 2H2SO4(aq) C6H5CH2OSO3H(s) + HSO4-(aq) + H3O+(aq)
Benzaldehyde is a simple, clear aldehyde formed by partial oxidation of benzyl alcohol and
readily oxidized to benzoic acid (chemicalland21.com/specialtychem/perchem/benzaldehyde.htm).

Figure 6.Chemical Structure of Benzaldehyde

Its reaction with sulfuric acid is shown as:
C6H5COH(aq) + 2H2SO4(aq) C6H5COSO3H(S) + HSO4-(aq) + H3O+(aq)
Lastly, those compounds insoluble in all the solvents used in the experiment were identified as
inert compounds (I). Hexane and toluene are inert compounds, defined as saturated carbons and are
compounds which are not chemically reactive because they dont have double or triple bonds and have
no leaving groups. Classified under this are haloalkanes or alkyl halides, aryl halides, deactivated
aromatic compounds, and diaryl ethers.
Hexane, C6H14, is an alkane (hydrocarbon) while toluene, C 7H8, is identified as an aromatic
hydrocarbon compound.

Figure 7.Chemical Structure of Hexane

Figure 8.Chemical Structure of Toluene

London dispersion forces are the only forces that can be applied to saturated hydrocarbons
because of their weak polarity. They are generally insoluble in water because of the incapacity to break its
hydrogen bonds.
Hexane is non-polar while sulfuric acid and water are polar; therefore, there is no reaction
formed. Meanwhile, sulfuric acid adds to toluene through electrophilic aromatic substitution.
(www.mendelset.com/articles/689/properties_hydrocarbons)

Summary and Conclusion

Solubility is the quantity of solute that can be dissolved in a solvent at a certain temperature. Its
solubility is important in knowing the composition of the solute and solvent to be used. There were
thirteen solutes, namely hexane, benzamide, acetone, ethyl alcohol, benzyl alcohol, aniline, toluene,
sucrose, benzaldehyde, benzoic acid and phenol, that was tested for their solubility with six different
solvents, distilled water, ether, 5% NaHCO3, 5% NaOH, 5% HCl and Conc. H2SO4, and was classified
either (+) soluble or (-) insoluble. After the experiment, the different solutes were grouped according to
their results. Sucrose was a water soluble compound while acetone and ethyl alcohol were ether and
water soluble compounds. Aniline was a basic compound while benzoic acid and phenol were both acidic
compounds but benzoic acid is a stronger acid and phenol is insoluble to NaHCO 3. Benzamide was
classified as miscellaneous neutral compound. Lastly, hexane and toluene were inert compounds while
benzyl alcohol and benzaldehyde were neutral compounds.

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Zimmerman, I. (2003). Elements of Organic Chemistry. New York, NY: Macimlla Publishing Co.,Inc.

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Solubility
of
Organic
Compounds.(n.d.).
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from
http://www.chem.ucalgary.ca/courses/351/laboratory/351expt_01_solubility.pdf on 06 February 2016.

DATA SHEET