UNIVERSITY OF SANTO TOMAS

FACULTY OF PHARMACY
ORGANIC CHEMISTRY LABORATORY

Organic Chemistry Laboratory – CH 200L (2012 – 2013) 2B-Ph Group 3 Experiment 7

CLASSIFICATION TESTS FOR HYDROCARBONS

Colleen C. Caragay, Rizzalaine P. Caringal*, Bett Shannen M. Carpio, Ancell Julienn C. Cruz, John Matthew
C. Cruz
Department of Pharmacy, Faculty of Pharmacy
University of Santo Tomas, Espana Street, Manila 1008

Date Submitted: Sept. 4, 2012

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Abstract

In the experiment, the organic compounds hexane, heptane, cyclohexane, cyclohexene, benzene and toluene
were subjected to physical tests to differentiate their intrinsic physical properties and chemical tests to determine their
chemical properties in terms of structure and behavior. The physical state was noted through the different color and odor
characteristics of each compound used. Miscibility was also tested by mixing a drop of each sample to 1 ml of
concentrated H2SO4. Flammability test was accomplished by placing 3-5 drops of each sample to a small evaporating dish
and lighting it with a match. Test for active unsaturation was completed by performing Baeyer’s and Bromine test. The test
for aromaticity of each compound was determined through Nitration. Lastly, the test for basic oxidation was performed
through the addition of 8 drops of 2% KMNO4 and 3 drops of 10% NaOH solution to 4 drops of each of the sample. All
the organic compounds are clear solutions with their own characteristic odor. Each compound was immiscible in
concentrated H2SO4 and flammable in the ignition test. All were not actively unsaturated except cyclohexene. Benzene
and toluene were found to be aromatic. All are not oxidized except cyclohexene.
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Introduction Another means of classification is dependent

The number of known organic compounds
totals into the millions. Of these compounds
are the simplest types called hydrocarbons.
Hydrocarbons are organic compounds
containing carbon and hydrogen atoms that are
covalently bonded to each other. Because of
the number and variety of hydrocarbons that
can exist, some means of classification is
necessary.
on the type of bonding that exists between
carbons. Hydrocarbons that contain only
carbon-to-carbon single bonds are called
alkanes which are also referred to as saturated
molecules. Hydrocarbons containing at least
one carbon-to-carbon double bond are called
alkenes, and compounds with at least one
carbon-to-carbon triple bond are called
alkynes. Both compounds are also referred to
as unsaturated molecules.

One means of classification depends on the

way in which carbon atoms are connected.
Aliphatic hydrocarbons are non-aromatic which
can be classified as acyclic and cyclic. Open- (Figure 1. Saturated Hydrocarbon of Alkane)
chained or acyclic hydrocarbons are
compounds consisting of carbons linked either
in a single or a branched chain. On the other
hand, closed –chained or cyclic hydrocarbons
are compounds that have carbon atoms linked
in a closed polygon or ring. (Figure 2. Unsaturated Hydrocarbon - Alkene)
Aromatic hydrocarbons are cyclic and planar. It
can be stabilized by resonance and it obeys
the Huckel’s rule (4n+2 = πe). Aromatic
hydrocarbons that contain alkyl side chains are
called arenes.

Six organic compounds was used in the

experiment, namely hexane, heptane,
(Figure 6. Cyclohexene)
cyclohexane, cyclohexene, benzene and
toluene. The first compound used was hexane.
Hexane is a hydrocarbon with the chemical
Benzene is an aromatic hydrocarbon
formula C6H14; that is, an alkane with
composed of 6 carbon atoms in a ring, with 1
six carbon atoms.
hydrogen atom attached to each carbon atom,
and with the molecular formula C6H6.

(Figure 3. Hexane) (Figure 7. Benzene)

On the other hand, n-Heptane is a straight-
chain alkane with the chemical formula
H3C(CH2)5CH3 or C7H16. The first two
compounds are both aliphatic and unsaturated
hydrocarbons.
Lastly, Toluene is also an aromatic
hydrocarbon which is a mono-
substituted benzene derivative, i.e., one in
which a single hydrogen atom from the
benzene molecule has been replaced by a
univalent group, in this case CH3.

(Figure 4. Heptane)

Cyclohexane is a cyclic hydrocarbon with

the molecular formula C6H12.
(Figure 8. Toluene)

Different tests were performed to be able to

differentiate hydrocarbons in terms of intrinsic
physical properties and chemical properties in
terms of structure and behavior. Various tests
were also accomplished to be able to analyze
(Figure 5. Cyclohexane)
a hydrocarbon and determine if it is saturated,
actively unsaturated, aromatic or an arene.
Cyclohexene is also a cyclic hydrocarbon with
the formula C6H10. It is unsaturated because of
The first test was done to determine the drugs
its double bond. Meanwhile, Cyclohexane is a
miscibility in Concentrated H2SO4. Miscibility is
saturated compound.
the property of liquids to to mix in all
proportions, therefore forming a homogenous
solution. By contrast, substances are
considered immiscible if in any proportion, they
do not form a solution. In organic compounds,
The miscibility is determined by the weight
percentage of the hydrocarbon chain.
The second test performed was ignition test to
determine the flammability and the presence of
unsaturation or high carbon to hydrogen ratio of
each organic compound. Flammability is the
measure of the extent to which a material or a
substance will support combustion. The degree
of luminosity can be assessed by the presence
of yellow flame and
Aromatic compounds burn with sooty flame due to
the incomplete combustion which causes the
formation of an unburned carbon. In terms of degree of
luminosity, aromatic compound > unsaturated
hydrocarbon > saturated hydrocarbon.
Baeyer’s test and Bromine test was performed to
determine which compound is actively unsaturated.
Baeyer’s test is a test for unsaturation or double bonds.
Baeyer’s test uses a solution called the
Baeyer’s reagent, which is a solution of
alkaline potassium permanganate. A positive
result or a compound which is actively
unsaturated leads to a result of decolorization
of a purple solution and formation of a brown
precipitate. Along with Baeyer’s test is the
Bromine test which is also a test for double
bonds. The reagent used is 0.5% Br2 in CCl4. A
positive result in the test will lead to
decolorization of an orange solution. The
compound which immediately decolorized
would be the most actively unsaturated
compound.
To determine for the Aromaticity of a
compound, Nitration test was accomplished.
The samples were reacted with HNO3 and
H2SO4. A positive result would produce a yellow
globule/ yellow oily layer.
The last test performed was Basic Oxidation, a
test for alkylated aromatics or arenes. The
reagents used were 2% KMnO4 and 10%
NaOH. A positive result in the test leads to a
violet solution (MnO4) or brown precipitate
(MnO2).
METHODOLOGY
There were six different compounds used in
the experiment, namely hexane, heptane,
cyclohexane, cyclohexene, benzene and
toluene. Different tests were performed to
determine the type of hydrocarbon used in
each sample.
A.) Physical State, Color and Odor
The first step in the experiment was to
determine the physical characteristics of the
samples. The physical state and color were
soot.
noted and the odor was recorded by wafting
each sample to determine its smell.
The first test accomplished was the test for
solubility or miscibility of the compound in
concentrated H2SO4.
B.) Solubility in Concentrated H2SO4
CAUTION!
CONCENTRATED H2SO4 IS
CORROSIVE AND DEHYDRATING.
(It is exothermic with water and may
react with water violently.)
A dry and calibrated dropper was used
to add a drop of the sample cautiously added
to about 1 ml of conc. H2SO4. The color
change or any warming effect was noted
immediately.
C.) Ignition Test
For the ignition test, 3-5 drops of the
sample was placed in a small evaporating
dish and lighted with a match. The
flammability, color of flame produced and
formation of soot was observed during the
test.
D.)Test for Active Unsaturation
Two different tests were accomplished
to check for the Active Unsaturation of a
compound.
a.)Baeyer’s Test
 In the Baeyer’s test, 2 drops of
2% KMnO4 was added to 5 drops of
the sample in a dry test tube. The
tube was shaken vigorously and the
rate and extent at which the reagent
is decolorized was observed. The
formation of a brown suspension was
also noted. Water as the negative
control was compared.
The last test was for alkylated aromatics or
arenes which was the Basic Oxidation test. 8
drops of 2% KMnO4 solution and 3 drops of
10% NaOH solution was added to 4 drops of
the sample in a test tube. Each test tube was
warmed in a water bath for 2 minutes and
the color change and formation of a brown
precipitate was observed.

b.) Bromine Test RESULTS / DISCUSSION

Besides the Baeyer’s test,

Bromine test was also performed. 10
drops of 0.5% Br2 in CCl4 was placed
with 5 drops of the sample in a dry
test tube. Similar to the Baeyer’s test,
the test tube was shaken vigorously
and the rate and extent by which the
reagent is decolorized was observed.
Water, as a negative control was also
compared. If the reaction failed to
decolorize within 1 minute, the
mixture was exposed to the sunlight.

E.) Test for Aromaticity: Nitration

The next test performed was the test

for Aromaticity through Nitration.

CAUTION!
CONCENTRATED H2SO4 IS
CORROSIVE AND DEHYDRATING.
2 ml CONCENTRATED
of conc. HNO3 HNO was3 IS
placed in an
Erlenmeyer flask. AND
CORROSIVE The flask was immersed in
OXIDIZING
an evaporating dish containing water and
was gradually added with 2 ml of conc.
H2SO4. The resulting mixture was cooled to
room temperature. The solution served as
the nitrating mixture. Then, 8 drops of the
nitrating mixture was added to 5 drops of
the sample in a dry test tube and was
shaken to ensure complete mixing. The
formation of a yellow oily layer or droplet
was noted. The mixture was then diluted
with 20 drops of water. The test tube was
placed in a water bath for 10 minutes if
there is no apparent reaction observed
within a minute.

F.) Basic Oxidation

 Compound Studies

Hexane Heptane Cyclohexane Cyclohexene Benzene Toluene

Condensed Structural Formula

A. Physical state at RT Liquid Liquid Liquid Liquid Liquid Liquid

Color Colorless Colorless Colorless Colorless Colorless Colorles
s

Strong Strong Strong odor Strong Strong odor Strong

odor odor odor odor
Odor
B. Solubility in concentrated Immiscible Immiscible Immiscible Miscible Immiscible Immisci
H2SO4 ble
Inference Not weak Not weak Not weak Weak base Weak base Not
base base base weak
base
C. Ignition Test Flammabl Flammabl Flammable Non Flammable Flamma
e e flammable ble
Inference Luminous Luminous Luminous Non Luminous Luminou
flame flame flame luminous flame s flame
flame
D. Baeyer’s Test No No No Immediate No No
decoloriza decoloriza decolorizatio decolorizati decolorizatio decolori
tion tion n on n zation
Bromine Test Slow Slow No Slow Slow Immedia
decoloriza decoloriza decolorizatio decolorizati decolorizatio te
tion tion n on n decolori
zation
Inference Saturated Saturated Not actively Not Not actively Not
saturated actively saturated actively
saturated saturate
d
E. Test for aromacity Immiscible Immiscible Immiscible, Immiscible, Immiscible, Immisci
nitration , oily layer , oily layer oily layer oily layer oily layer, ble, oily
slightly layer,
yellow slight
yellow
Inference Not Not Not aromatic Not Not aromatic Aromati
aromatic aromatic aromatic c
F. Basic Oxidation No No No No No Fast
decoloriza decoloriza decolorizatio decolorizati decolorizatio decolori
tion tion n on n zation
The physical characteristics of each sample
were noted. All the organic compounds used
are clear, colorless liquid. Each compound
has their own characteristic odor that makes
them distinguishable from the others.
The solubility or miscibility of the compounds
in H2SO4 indicates whether the sample is a
very weak base (can be protonated) or a
neutral compound (cannot be protonated).
The dissolution of compounds in H2SO4 may
also produce large amounts of heat and/or a
change in the color of the solution,
precipitation or any combination of these.
*H2SO4
-soluble (very weak base)
Esters, Ketones, Alkenes, Aldehydes Alcohols
*H2SO4
-insoluble (neutral compound)
Alkanes, Aryl halides, Alkyl halides,
most aromatic hydrocarbons
The ignition test was performed to indicate the
presence of unsaturation or high carbon to
hydrogen ratio. Generally, high carbon to hydrogen
ratio equals high luminosity and the more the flame
produces black smoke or soot. The degree of
luminosity can be assessed by the presence of
yellow flame and soot. Aromatic compounds burn
with sooty flame due to the incomplete combustion
which causes the formation of an unburned carbon.
Aromatic compound is greater than unsaturated
hydrocarbon, and unsaturated hydrocarbon is
greater than saturated hydrocarbon in terms of
degree of luminosity. Complete combustion is
indicated by a blue flame (non-luminous) and there
is more heat than light; hence the carbon is
completely oxidized. On the other hand, incomplete
combustion is indicated by a yellow flame
(luminous) and there is much light than heat;
hence the carbon is not completely oxidized.
Complete combustion
CxHy + O2 CO2 + H2O
Incomplete combustion
CxHy + O2 CO2 + CO + C(soot) + H2O
The test for Active Unsaturation was accomplished
in two ways: Baeyer’s test and Bromine test. Both
determine the presence of double bond in each
organic compound.
In the Baeyer’s test, the reagent used was 2%
KMnO4 solution. The positive result that must be
obtained in the test is the decolorization of a purple
solution followed by formation of a brown
precipitate. All but cyclohexene gave a negative
result to the test. It indicates that cyclohexene is
positive for the active unsaturation test and that it
contains double bond in its chemical structure. In
the reaction, Mn7+ is reduced to Mn4+ which means
that alkene is oxidized to a diol in the process of
redox reaction. Alkenes react with potassium
permanganate (KMnO4) to give a diol and MnO2.
Aromatic compounds do not react in this test
because of their stability.
Cyclohexene + KMnO4 1,2-cyclohexanediol + MnO2
(purple) (colourless) (brown)
The reagent used in Bromine test was 0.5% Br2 in
CCl4. A positive result is obtained by
decolorization of an orange solution. In this
case, cyclohexene decolorized immediately
and became a clear solution while the other
compounds still needed exposure to UV light
in order to decolorize. From there, the test
readily gave a positive result to cyclohexane
which makes it actively unsaturated in the
two different tests performed. The alkenes
react with Br2 to form a trans-
dibromoalkane. The reaction involves
electrophilic addition. Aromatic compounds
do not react because of their stability;
however, they will react slowly upon using
FeBr3 or through the action of UV light.
The test for Aromaticity was performed
through Nitration. The reagents used were
HNO3 and H2SO4. A positive result in the test
is obtained when a yellow oily layer is
formed. Benzene and toluene gave a positive
result and therefore the two compounds are
considered aromatic. Other than that, the
two compounds are also cyclic and planar in
their chemical structure and they obey
Huckel’s rule that is why they are considered
aromatic compounds. The H2SO4 acts as a
catalyst and facilitates the formation of
nitronium ion (NO2+), an electrophile.
Onehydrogen in the benzene ring is
substituted by the nitronium ion that is why
the reaction involves electrophilic
substitution.
HNO3 + H2SO4 NO2+ + 2H2SO4- + H3O+
Benzene + NO2+ nitrobenzene
The last test performed was Basic Oxidation,
a test for alkylated aromatics or arenes. The
reagents used were 2% KMnO4 and 10%
NaOH. A positive result in the test will
produce a violet solution (MnO4) or brown
precipitate (MnO2). NaOH provides a basic
environment. The alkyl group of the aromatic
compound is oxidized to a carboxylic acid,
therefore involves a redox reaction. Mn7+ is
reduced to Mn6+/4+ depending on the extent
of the reaction.
Methylbenzene + KMnO4 benzoic acid + MnO4
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Introduction to General, Organic and
Biochemistry. USA: Brooks/ Cole
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Eighth Edition. Singapore: McGraw-Hill
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Tests for Hydrocarbons.
http://www.scribd.com/doc/25377353
/Classification-Tests-for-Hydrocarbons
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Laboratory Manual
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http://www.scribd.com/doc/24691082
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