ACTIVITY # 8 chemical principle underlying three major
techniques you will study in the organic
SOLUBILITY OF ORGANIC
COMPOUND
ABSTRACT
The method or process of separating
different mixtures of liquids based on their
differences in volatility using evaporation-
condensation process are known
distillation. Distillation is done with the use
of specific set-up, using the
distillation apparatus. Through this process,
the identities of the components in the
solution can be determined through the
obtained boiling points. In this experiment,
we determined on how to acquire basic
skills of conducting simple and fractional
distillation, separate components of the
liquid mixture and compare the efficiency of
separation of each method.
At the end of our experiment, we
found out that methanol has a very low
boiling point the reason why it condensed
first and mostly left in the boiling flask.
I. INTRODUCTION
The solubility of a solute
dissolved substance) in a solvent (the
dissolving medium) is the most important
chemistry laboratory: crystallization,
extraction, and chromatography. In this
experiment on solubility you will gain an
understanding of the structural features of a
substance that determine its solubility in
various solvents. This understanding will
help you predict solubility behavior and
understand the techniques that are based on
as
this property.
proper Five common reagents are used for
solubility tests: (1) water, (2) 5% NaOH, (3)
5% NaHCO3, (4) 5% HCl, and (5)
concentrated (96%) H2SO4. Except in the
case of water, solubility experiments probe
the acid-base properties of organic
compounds. If a compound is an acid, you
can obtain a relative measure of its acid
strength by testing it against the weak base
sodium bicarbonate and the stronger base
sodium hydroxide. Naturally, any organic
compound that is soluble in water is also
likely to be soluble in 0.6 M NaHCO3, 1.5M
HCl, and 2.5 M NaOH solutions because
these solutions are composed largely of
water.
(a II. OBJECTIVES
1. To explore the relative solubility of
organic compounds in a particular solvent.
2. To understand the relative solubility
of organic compounds in various solvents.
3. To determine the functional group of
an unknown organic compound.
III. METHODOLOGY & SET-UP
solid) to determine whether the
compound is very soluble or slightly
soluble. Record your observations
and determinations of solubility in
the data table.
I – Insoluble, SS – Slightly

Materials: Soluble, VS – Very Soluble

Properly dispose the solution.
(5) 10-mL Test Tubes
Dispose all aqueous solution in the
(1) Hot Plate
Aqueous Waste Container. Leftover
(2) 250-mL Beaker
organic compounds should be
(1) Unknown Organic Compound
disposed on either halogenated or
(1) Test Tube Rack non-halogenated Organic Waste
Procedure: container.

A. General Procedure
B. Solubility of Alcohols

Place approximately 1mL of the test

solvent into a small test tube. Add 3 1. Take 1mL of distilled water and add

drops of the liquid (or a few crystals 3 drops of Methanol. Note the

of the solid) test substance to the results.

solvent. Stir by gently tapping the 2. Repeat the experiment using other

test tube with your finger. Determine alcohols: Ethanol, Propanol, 1-

if the small amount of compound Butyanol, and Tert. Butyl Alcohol

dissolves immediately (if not you 3. In another test tube, add 1mL of

may need to stir more, wait a few Hexane and add 3 drops of

minutes or use a very gentle Methanol. Note the results.

heating)/ If the small amount does 4. Repeat the experiment using other

not dissolve, the compound is alcohols: Ethanol, Propanol, 1-

insoluble in that solvent. If the Butyanol, and Tert. Butyl Alcohol

sample does dissolve, add several

more drops of liquid (or crystals of
 C. Solubility of Various Organic 2. Repeat the experiment using other
Compounds in Different Solvents solvents: 2.5 M NaOH, 0.6M NaHCO3,
1.5 M HCl, Concentrated H2SO4.
I. Solubility of Glacial Acetic Acid
IV. Solubility of Ethyl Acetate
1. Perform the water test first on all
compounds. If the compound is soluble 1. Take 1mL of distilled water and add a
in water, test the aqueous solution with 3 drops of Ethyl Acetate. Note the
red and blue litmus paper. Use the results.
stirring rod to place 1 drop of the
2. Repeat the experiment using other
solution to the litmus paper. Do not solvents: 2.5 M NaOH, 0.6M NaHCO3,
perform the litmus paper test on 1.5 M HCl, Concentrated H2SO4.
compounds that are not soluble in water.
V. Solubility of Hexane
2. Take 1mL of distilled water and add 3
1. Take 1mL of distilled water and add 3
drops of Glacial Acetic Acid. Note the
drops of Hexane. Note the results.
results.
2. Repeat the experiment using other
3. Repeat the experiment using other
solvents: 2.5 M NaOH, 0.6M NaHCO3,
solvents: 2.5 M NaOH, 0.6M NaHCO3,
1.5 M HCl, Concentrated H2SO4.
1.5 M HCl, Concentrated H2SO4.
VI. Solubility of Benzaldehyde
II. Solubility of Benzoic Acid
1. Take 1mL of distilled water and add 3
1. Take 1mL of distilled water and add a
drops of Benzaldehyde. Note the results.
pinch of Benzoic Acid. Note the results.
2. Repeat the experiment using other
2. Repeat the experiment using other
solvents: 2.5 M NaOH, 0.6M NaHCO3,
solvents: 2.5 M NaOH, 0.6M NaHCO3,
1.5 M HCl, Concentrated H2SO4.
1.5 M HCl, Concentrated H2SO4.
D. Determination of the functional
III. Solubility of Phenol
class of an unknown organic
1. Take 1mL of distilled water and add 3
compound
drops of Phenol. Note the results.
 1. Take 1mL of distilled water and add 3
drops of an unknown compound. Note
the results.
2. Repeat the experiment using other
solvents: 2.5 M NaOH, 0.6M NaHCO3,
1.5 M HCl, Concentrated H2SO4.
3. Identify the functional class of your
unknown.
IV. DATA RESULTS
V. DISCUSSION
At the molecular level, solubility is
controlled by the energy balance of
intermolecular forces between solute –
solute, solvent – solvent and solute – solvent
molecules. Intermolecular forces come in
different strengths ranging from very weak
induced dipole – induced dipole interactions
to much stronger dipole – dipole forces
(including important special case, hydrogen

Legend: bonding). However, there is a simple, very

useful and practical empirical rule that is
I – Insoluble
quite reliable. That simple rule is “like
SS – Slightly Soluble dissolves like” and it is based on the polarity
of the systems (i.e.: polar molecules
VS - Very Soluble
dissolves in polar solvents and non-polar
A. Solubility of Alcohol molecule in non-polar solvents). This is why
ALCOHOLS WATER HEXANE ionic compounds (take salt for an example)
Methanol VS I or sugar dissolves in water but do not
Ethanol VS SS
Propanol VS VS dissolve to any great extent in most organic
1-Butanol SS SS solvents. It also applies to the separation of
tert-Butyl I SS
Alcohol oil and water. The polarity of organic
molecules is determined by the presence of
polar bonds due to electronegative forms in
B. Solubility of Various Organic
polar functional groups such as amines and
Compound
alcohols.
ANSWER ATTACHED ON THE LAST
The solubility of a substance is a
PAGE
measure of the equilibrium between the
C. Functional Class of Unknown: substance in its solid state and substance, or
Alkanes (Hexane) its ions in solution. It can also be defined as
 the maximum amount of solute that can be containing several polar groups. The
dissolved in a fixed amount of solvent at a presence of an acidic –CO2H or –NH2
specific temperature. group in water – soluble compound can be
detected by low or high pH.
Since the polarity of an organic
molecule is related to the presence of polar Compounds that are insoluble in
bonds that are found within functional water can be soluble in aqueous
groups, the solubility characteristic of environment if they form ionic species when
organic compounds can provide treated with an acid or base. This is because
experimental evidence for the presence or the ionic form is much more polar.
absence of several important organic
The solubility of carboxylic acids
functional groups.
(pKa = 3 to 5) and phenols (pKa = 9 to 10)
SOLVENTS SOME SOLUBILITY / in aqueous hydroxide is due to formation of
COMPLETE
the polar (ionic) carboxylate or phenoxide
MISCIBILITY
Water alcohols, amines, acids, groups since they are much stronger acids
esters, ketones, aldehydes than water (pKa = 15) and therefore the acid
5% NaOH carboxylic acids and
phenols – base equilibrium lies far to the right,
5% NaHCO3 carboxylic acids which is the more polar side.
5% HCl Amines
Concentrated most organic molecules The solubility of amines in dilute
H2SO4
aqueous acid similarly reflects the fact that
they are stronger bases than water, and are
Most organic molecules are
converted by reaction with proton to the
relatively non-polar and usually soluble in
polar ammonium ions.
organic solvents but not in polar solvents
like water. However, some organic Unknown Substance (Compound)
molecules are more polar and therefore There are three kinds of information
soluble in water. This denotes a rather high that can be obtained in identifying an
ratio of polar groups to non – polar unknown compound by the study of its
hydrocarbon chain (i.e.: a low molecular solubility in water, 5% NaOH solution, 5%
weight compound containing an –OH, - NaHCO3 solution, 5% HCl solution, and
NH2, or -CO2H group or a larger molecule concentrated H2SO4:
• The presence of functional group can
be detected. For an instance, since
hydrocarbons are soluble in water, the mere
fact that an unknown is partially soluble in
water indicates that a polar functional group
is present.
• Solubility in certain solvents gives
more specific information about the
functional groups. For example, benzoic
acid is insoluble in a polar solvent, water,
but is converted into 5% NaOH solution to
salt, sodium benzoate which is readily water
soluble then the solubility in 5% NaOH
solution of a water insoluble unknown is a
strong indication of an acidic functional
group.
• Deductions about molecular size and
composition can be made sometimes. For
example, in many homologous series of
monofunctional compounds, the members
with fewer than about 5 carbon atoms are
water soluble, wheras the higher homologs
are insoluble.
Since most organic molecules have both a
polar and non – polar entity, it can be
deduced that its solubility would depend on
the balance between two parts. As the
percentage of the hydrocarbon portion
increases while the polar solvent decreases
while that in non – polar solvent increases.
Water
This is a polar solvent which
dissolves polar compounds. Several
structural features of the unknown can be
deduced if it is water – soluble. It must be of
low molar mass and will usually contain no
more than four to five carbon atoms, unless
it is polyfunctional. It must contain a polar
group that will form a hydrogen bond with
water like the hydroxyl group of alcohol or
carboxylic acid, the amino functionality of
an amine or the carbonyl group of aldehydes
or ketones. Ester, amides and nitriles
dissolve to a lesser extent and acid chlorides
or anhydrides react with water rather than
simply dissolving in it. On the other hand,
alkenes, alkenes, alkynes and alkyl halides
are water – soluble.
5% NaOH
Compounds dissolve in aqueous base
solutions because they for sodium salts that
are soluble in aqueous medium. However,
the salts of some high molecular weight
compounds are not soluble and will just
precipitate.
Both phenols and carboxylic acids
produce resonance stabilized conjugate
bases. In phenols, substitution of an electron
withdrawing group at the ortho and para
positions od the ring increases the acidity.
Phenols with 2 or 3 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 to
their water – soluble acids and phenols
which are weak acids dissolve in NaOH
because they are converted into their water –
soluble sodium salts.
5% NaCO3
When a compound is insoluble in
water but soluble in NaOH, it is either a
weak or a strong acid. Testing its unknown
solubility ins NaCO3 which is less basic
than NaOH will differentiate strong acids
from weak acids. As Strong acids can easily
be deprotonated and can attack even a weak
base such as NaCO3 so they are soluble in
solvent. Weak acids do not react with weak
bases.
5% HCl
If the compound is soluble in HCl
but insoluble in water, an amine should be
considered immediately. Aliphatic amines
(RNH2) are basic compounds which readily
dissolves in an acid because they from
hydrochloride salts that are soluble in
aqueous medium.
Concentrated H2SO4
Concentrated H2SO4 protonates all
organic compounds that contains oxygen
and/or nitrogen, as well as alkenes and few
aromatic hydrocarbons. They exist as isonic
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 acid,
and an oxygen – containing compound
becomes protonated in concentrated acid to
from soluble oxonium salt.
Compounds which are insoluble in
sulfuric acid are extremely weak base. It is
the extreme acidity of concentrated sulfuric
acid along with its powerful ionizing ability
that allows these compounds to be soluble in
slfuric acid. Thus is able to protonate
alcohols, ketones, aldehydes, esters, and
unsaturated hydrocarbons. The resulting
ions produced are soluble in the medium.
VI. CONCLUSION
In this activity, we have concluded that
distillation is a great method in separating
mixtures of liquids by using evaporation-
condense technique. We found out that
while simple distillation separated the
majority of the two compounds near the
beginning and the end of the distilling
process, fractional distillation produced
much more pure fractions.
Lastly, we conclude that fractional
distillation is more efficient to used in this
experiment because it separate the mixture
and produced pure collection of
distillated compound.
are completely miscible. They dissolve in
water in any amount. Starting with the four-
carbon butanol the solubility of alcohols is
starting to decrease.
2. Construct a solubility flow scheme for
the results in part B.
the ANSWER ATTACHED ON THE LAST
PAGE

VII. ANSWERS TO QUESTIONS

1. Arrange the alcohols in increasing

solubility in water. Explain the trend. This is to certify that the following
members of the group participated in the
Methanol – Ethanol – Propanol – 1-butanol – preparation of this report.
tert-butyl alcohol

Each alcohol consists of a carbon

chain (always nonpolar) and a OH group
Rochelle Joyce O. Bersamin
(which is polar). For ethanol for example the
chemical formula looks like this: C2H5OH.
Ethanol has a 2 carbon chain and an OH
group. As water is polar it attracts OH
Christine Grace B. Infante
group. Carbon chain on the other hand as
non-polar is repelled. Solubility of alcohols
is therefore determined by the stronger of
the two forces.
Khyscia Judenly R. Lagarto
Because of the strength of the
attraction of the OH group, first three
alcohols (methanol, ethanol and propanol)