CLASSIFICATION TESTS FOR HYDROCARBONS

Dedan Angelo B. Samson, Bernadette Mae L. Segismundo, Jane Darylle G. Semilla,

Jason Anthony T. Supea, Francis Ernest R. Talusan and Aniko Carlo S. Tendenilla
Group 7 2B Medical Technology Organic Chemistry Laboratory
ABSTRACT
In the performed experiment, there were six hydrocarbons used namely, Hexane, Heptane, Cyclohexane,
Cyclohexene, Benzene and Toluene. They were described and identified according to their physical state at room
temperature, appearance, their color and also their odor. They were also classified according to their solubility in
concentrated H2SO4, flammability, active unsaturation, aromaticity and oxidation. Their physical state was a colorless
liquid form and they also varied in odor. In the solubility test, it was conducted in a 1 mL concentrated H2SO4 t
determine if it is miscible or immiscible. Flammability test or the ignition test was conducted by placing 3-5 drops of
sample in an evaporating dish and lighting it with a match. Formation of soot was also observed in ignition test. There
were two tests for the active unsaturation test, the Baeyers test and the Bromine test. In Baeyers Test, 2% KMnO 4
solution was added in the sample and decolorization was observed that gave positive result. In Bromine test, 10 drops
of 0.5% of Br2 in CCl4 reagent is added was added to the sample. Immediate decolorization was observed and gave
positive result. For the test of aromaticity, the process of Nitration is used. It was conducted to determine the
miscibility of the hydrocarbons by adding 8 drops nitrating mixture that composed of concentrated HNO 3 to a 5 drops
sample that formed a yellow oily layer or droplet and water bath was conducted. Lastly, the test of basic oxidation
was conducted to know if precipitate was formed when 4 drops of sample was added with 2% KMnO 4 solution, distilled
water and 10%NaH solution. All but cyclohexene exhibited immiscibility in concentrated H 2SO4 and in flammability test
but only hexane and heptane did not have soot. All except for cyclohexene were not actively unsaturated.
Cyclohexene, benzene and toluene were observed to be aromatic. All but cyclohexene were not oxidized.

INTRODUCTION
Hydrocarbons are the simplest organic compounds.
It can be classified as an aromatic hydrocarbons or
aliphatic
hydrocarbons.
Aromatic
hydrocarbon
contains alkyl side chains that are called arenes.
Hydrocarbons are considered to be aromatic when
they follow the Huckels Rule. And their structures
are stabilized by a resonance and are cyclic. The
aliphatic hydrocarbons, which are saturated, are
alkanes, and if found in a closed chain, it is termed
as a cycalkanes. If they are unsaturated, they can be
an alkene or cycloalkene, alkyne or cycloalkyne.
Carbons of saturated hydrocarbon are bonded by
singe covalent bonds and it creates the maximum
number of hydrogen in a compound due to the
absence of any substituent. Hydrogen usually
occupies all the available bonding positions in carbon
after bonding with each other. On the other hand,
unsaturated hydrocarbon contains triple or double
bond. The objectives of this experiment were to
identify and classify the different hydrocarbons. This
experiment also aims to identify the different physical
and chemical properties of hydrocarbon compounds.
The hydrocarbons were to be tested according to
their solubility, flammability, active unsaturation,
aromaticity, and basic oxidation. To elaborate, they
were categorized based on the results inferred;
whether miscible or immiscible, saturated or
unsaturated, actively unsaturated or not actively
unsaturated, aromatic or not aromatic, and oxidized
or not.

EXPERIMENTAL
A. Compounds tested (or Samples used)

Figure 1. Structure of Hexane

Hexane is an alkane with six carbon atoms and
has the chemical formula C6H14. Hexanes are
significant constituents of gasoline. They are
colorless liquids at room temperature and
odorless when pure, the boiling points are
between 50C and 70C. They are widely used
as cheap and relatively safe, largely unreactive,
and easily evaporated non-polar solvents.

Figure 2. Structure of Heptane

Heptane is a straight-chain alkane with the
chemical formula H3C(CH2)5CH 3 or C7H16. The
structure of heptane with angled bonds, with all
atoms is explicitly shown. Heptane (and its
many isomers) is widely applied in laboratories
as a totally non-polar solvent. As a liquid, it is
ideal for transport and storage.

Figure 3. Structure of Cyclohexane

Cyclohexane is a cycloalkane with the molecular formula
(CH2)6. Cyclohexane is a colorless, flammable liquid
with a distinctive detergent-like odor, reminiscent of
cleaning products (in which it is sometimes used).
Cyclohexane is mainly used for the industrial
production of adipic acid and caprolactam, which are
precursors to nylon.

Figure 4. Structure of Cyclohexene

Cyclohexene is a hydrocarbon with the formula C 6H10.
This cycloalkene is a colorless liquid with a sharp smell.
It is an intermediate in various industrial processes.
It is sweet in odor and is insoluble in water and
miscible with organic solvents.

Figure 5. Structure Benzene

Benzene is an organic compound with the molecular
formula C6H6. Its molecule is composed of 6 carbon
atoms joined in a ring, with 1 hydrogen atom
attached to each carbon atom. It is a colorless liquid
with an aromatic and gasoline-like odor. It is soluble
in alcohol, CHCl3, CCl4, diethyl ether, acetone and
acetic acid.

Figure 6. Structure of Toluene

Toluene, formerly known as toluol, is a colorless,
water-insoluble liquid with the typical smell of paint

thinners. It is a mono-substituted benzene. Its

molecular formula is C7H 8. It is an aromatic
hydrocarbon that is widely used as an industrial
feedstock and as a solvent and is sometimes
also used as an inhalant drug for its
intoxicating properties. Toluene is an important
organic solvent, but is also capable of
dissolving a number of notable inorganic
chemicals such as sulfur, iodine, bromine,
phosphorus, and other non-polar covalent
substances.

B. Procedure
Physical State, Color and Odor
The physical appearances of the samples
were observed at room temperature. The odor
of the samples was obtained with a wafting
motion of the hand over the mouth of the test
tube.
Solubility in concentrated H2SO4
A dry and calibrated dropper was used to add
a drop of the sample to 1mL of concentrated
H2SO4. Any color change and/or warming effect
were noted.
Ignition Test
3-5 drops of the sample were placed in a
small evaporating dish and lighted with a
match. Any flame produced was noted as well
as the flame color and soot produced, if any.
Test for Active Unsaturation
a) Baeyers Test
2 drops of 2% KMnO4 solution were
added to 5 drops of the sample in a dry
test tube. The test tube was shaken
vigorously to observe the rate and
extent at which the reagent is
decolorized. Any formation of brown
suspension was noted. It was compared
with water as a negative control.
Decolorization
of
the
reagent
is
considered immediate if it occurs within
1 minute.
b) Bromine Test
10 drops of 0.5% Br 2 in CCl4 reagent
was added to 5 drops of sample in a dry
test tube. The test tube was shaken
vigorously to observe the rate and
extent (color change) at which the
reagent is decolorized or when the
bromine color is discharged. It was
compared with water as a negative
control. If the reagent failed to
decolorize within 1 minute, the reaction
mixture must be exposed to sunlight.

Test for Aromaticity: Nitration

First, a nitrating mixture was prepared by gradually
adding 2mL of concentrated H2SO4 to a 2mL
concentrated HNO3 in an Erlenmeyer flask immersed
in an evaporating dish containing water. After cooling
the resulting mixture to room temperature, 8 drops
of this nitrating mixture will be added to 5 drops of
the sample in a dry test tube. The formation of
yellow oily layer or droplet was noted. If there is no
apparent reaction observed within 1 minute, the test
tube must be placed in a water bath (~50C) for 10
minutes.
Basic Oxidation
8 drops of 2% KMnO 4 solution and 3 drops of 10%
NaOH solution were added to 4 drops of sample in a
test tube. The test tub tubes were placed in a water
bath for 2 minutes. Any color change or formation of
brown precipitate was noted.

the solution followed by the formation of brown

precipitate. All of the samples produced
negative results in this test except for
cyclohexene. Cyclohexene contains a double
bond
which
reacts
with
potassium
permanganate (KMnO4) producing a diol and
MnO2. Most aromatic compounds do not react
in this test due to their stability.

Figure 7. Baeyers Test

(purple solution: saturated)

RESULTS AND DISCUSSION

The physical characteristics of the hydrocarbon
compounds in room temperature were noted. All of
the samples have colorless, liquid appearance and
each has its own odor that makes it distinguishable
from others.
In the test for the solubility in sulfuric acid (H 2SO4),
all of the samples were observed to have an oily
layer. This is due to hydrocarbons being non-polar
compounds
and
sulfuric
acids
being
polar
compounds. Thus, they are not attracted to each
other resulting to the immiscibility of hydrocarbons to
sulfuric acid except for cyclohexene because
The ignition test was performed to test the
luminosity
of
the
hydrocarbon
compounds.
Compounds with high carbon to hydrogen ratio
exhibits high luminosity. Aromatic hydrocarbons are
highly
luminous
compared
to
unsaturated
hydrocarbons and unsaturated hydrocarbons are
more luminous than saturated hydrocarbons. The
degree of luminosity can be assessed by the
presence of yellow flame and soot (unoxidized
carbon) due to incomplete combustion. In incomplete
combustion, there is more light than heat produced
indicated by a yellow flame (luminous), while in
complete combustion, there is more heat than light
produced indicated by a blue flame (non-luminous).
All of the organic compounds exhibited a luminous
fame and only hexane and heptane have no soot.
The Baeyers test and the Bromine test were
performed to assess the active unsaturation of
hydrocarbon compounds.
In Baeyers test, the active unsaturation of a
compound is indicated by a purple decolorization of

Figure 8. Baeyers Test

(dissolution of purple solution resulting to
brown precipitate: unsaturated)
In Bromine test, the active unsaturation of a
compound is indicated by a decolorization of
the solution. The only compound that gave a
positive result for this test is cyclohexene
producing a colorless solution. Cyclohexene
reacted with Br2 producing trans-dibromoalkane
through electrophilic
addition.
All other
compounds, mostly aromatic, needed to be
exposed to UV light in order to undergo
decolorization. However, decolorization with
exposure to UV light does not classify them
under actively unsaturated compounds. Alkanes
contain only sigma bonds and cannot add to Br
so the reddish brown color of Br dilutes to
yellow or orange solution under the sunlight.
Aromatic carbons, on the other hand, are
extremely stable and will not react without a
catalyst. Only cyclohexene passing both
Baeyers and Bromine tests is considered
actively unsaturated.

Figure 9. Bromine Test

(yellow solution: no reaction/saturated)

Figure 10. Bromine Test

(reddish brown color of Bromine disappears resulting
to colorless solution: with reaction/unsaturated)
The test for the aromaticity of the compounds was
performed through nitration. The aromaticity of the
compound is indicated by a yellow oily layer.
Benzene and toluene are the only compounds which
gave positive results in this test. Other than nitration,
the aromaticity of compounds can be assessed by
their cyclic and planar chemical structures and if they
follow Huckels rule which applies to both benzene
and toluene.
The last test which is basic oxidation was performed
in order test the oxidation of the hydrocarbons. A
positive result is indicated by producing a violet
solution or a brown precipitate. All the compounds
were not oxidized except cyclohexene. The double
bond in cyclohexene is susceptible to oxidations
forming 1,2-diols and MnO2 (brown precipitate) in
this test.

Table 1. Results of the Classification Tests of Hydrocarbons

Compounds Studied
Hexane

Heptane

Cyclohexane

Cyclohexene

Benzene

Toluene

Liquid

Liquid

Liquid

Liquid

Liquid

Liquid

Clear
Colorless
Slight gasoline
odor
Formation of
oily layer

Clear
Colorless
Petroleum
odor
Formation of
oily layer

Clear
Colorless
Petroleum
odor
Formation of
oily layer

Clear
Colorless
Gas-like odor
Formation of
orange oily
layer

Clear
Colorless
Gas-like
odor
Formation
of clear oily
layer

Clear
Colorless
Rugby-like
odor
Formation
of clear oily
layer

Inference

Immiscible

Immiscible

Immiscible

Miscible

Immiscible

Immiscible

C. Ignition
Test

Flammable, no
soot

Flammable, no
soot

Flammable,
with soot

Flammable,
with soot

Flammable,
with soot

Flammable,
with soot

Inference

Luminous
flame
No
decolorization

Luminous
flame
No decolorization

Luminous
flame
No
decolorization

Luminous
flame
No
decolorization

Luminous
flame
No
decolorization

Slowly
decolorized
(orange to
colorless)
Not actively
unsaturated
Clear oily layer

Slowly
decolorized
(orange to
colorless)
Not actively
unsaturated
Clear oily layer

Slowly
decolorized
(orange to
colorless)
Not actively
unsaturated
Clear oily
layer

Luminous
flame
Immediate
decolorization, brown
precipitate
Immediate
decolarized
(orange to
colorless)
Actively
unsaturated
Yellow oily
layer

No
decolorization

No
decolorization

Not actively
unsaturated
Yellow oily
layer

Not actively
unsaturated
Yellow oily
layer

Inference

Not aromatic

Not aromatic

Not aromatic

F. Basic
oxidation

No
decolorization

No
decolorization

Inference

Not oxidized

Not oxidized

No
decolorization
Not oxidized

Condensed
Structural
Formula

A. Physical
State at RT
Appearance
Color
Odor
B. Solubility
in
concentrated
H2SO4

D. Baeyers
Test
Bromine Test

Inference
E. Test for
aromaticity:
Nitration

Aromatic
Violet t
brown
Oxidized

Aromatic

Aromatic

No
decolorization
Not oxidized

Immediate
decolorization
Not oxidized

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