Classification Tests for Hydrocarbons

Jasareno, K.L.S., Juguilon, I.M.M., Limsi, K.E.H., Llanita, A.J.I., Lopez, S.S.C., and
Macaranas, J.D.P.
2B-PH, Group No. 5, Department of Pharmacy, Faculty of Pharmacy, University of Santo
Tomas, Espaa Boulevard, 1015 Manila, Philippines
Abstract
In this experiment the group used 5 sample organic compounds, Hexane, Heptane,
Cyclohexane, Cyclohexene, Benzene and Toluene. These compounds were observed in terms of
intrinsic physical properties and chemical properties in terms of structure and behavior. The
compounds were subjected to the several tests available to classify hydrocarbons. The main
objective of this experiment was for the group to be familiar with the different properties and
reaction mechanisms that characterize the different classifications of hydrocarbons.
Introduction
Hydrocarbons are one of the basic
organic compounds there is.[6] A
hydrocarbon, as its name implies, consists of
only covalent hydrogen-carbon bonds.
These organic compounds are mainly
classified as aliphatic or aromatic. Aliphatic
hydrocarbons are classified according to its
carbon chain skeleton, acyclic (openchained) or cyclic (closed-chained). Also,
according to the bonds present, saturated
hydrocarbons which only have single
covalent bonds or unsaturated hydrocarbon
which have at least a double or triple
covalent bond in its structure. Aromatic
hydrocarbons are mainly composed of
benzenes (Fig. I.5.), those that contain alkyl
side chains are called arenes.[] In the
experiment, six different organic compounds
were used namely, hexane, heptane,
cyclohexane, cyclohexene, benzene and
toluene. For every classification of the given
samples of hydrocarbons, there is a
corresponding test that would help identify
it. The importance
of classifying
hydrocarbons is that it enables researchers to
identify the certain characteristic that would

either be beneficial or harmful towards its

intended use.[6]
The intended learning outcomes of
this experiment are to analyze and classify
hydrocarbons, differentiate hydrocarbons in
terms of their intrinsic physical properties
and chemical properties based on their
structure and behavior.[1]
Methodolgy
For this experiment, the group used
the following organic compounds: hexane,
heptane, cyclohexane, cyclohexene, benzene
and toluene to differentiate each with the aid
of several tests.
A. Physical State, Color and Solubility
First, the physical state, color and
odor of the samples were taken note of.
B. Solubility in conc. H2SO4
1 mL of concentrated H2SO4 was
placed in 6 different test tubes, then one
drop of each sample was added to the test
tubes. Any color, odor and formation of
precipitates or layers were then taken note of
after mixing.[1]

C. Ignition Test
3-5 drops of each liquid sample was
placed in a small evaporating dish, for the
solid samples a pinch amount was used, the
samples were then lit with a match.
Flammability, formation of soot and flame
color was noted for each sample afterwards.
[1]
D. Test for Active Unsaturation
a. Baeyers Test
5 drops of the sample was placed
in a dry test tube. 2 drops of KMnO4
was added to the solution. The test
tube was shaken vigorously and the
rate and extent of decorization was
observed. The formation of a brown
precipitate was taken note of and the
sample was compared with water as
the negative control. Decolorization
under a minute was recorded as
immediate.[1]
b. Bromine Test
10 drops of 0.5% Br2 in CCl4
reagent was added to 5 drops of the
sample in a dry test tube. The test
tube was shaken vigorously and the
rate of color change was observed.
Water was used as a negative control
to compare. Samples that did not
decolorize within a minute were
exposed to sunlight. Results were
taken note of.[1]
E. Test for Aromaticity: Nitration
For the formation of the nitrating
mixture, 2 mL of concentrated HNO3 was
placed in an Erlenmeyer flask and was
immersed in an evaporating dish that
contained water. 2 mL of concentrated

H2SO4 was gradually added. The resulting

mixture was cooled at room temperature.
8 drops of the nitrating mixture was
added to 5 drops of the sample and was
shaken to ensure complete mixing. The
formation of a yellow oily layer or globule
was noted and the solution was diluted with
20 drops of water. Solutions that did not
react within a minute were placed in a water
bath for 10 minutes and diluted with 20
drops of water. The results were taken note
of after.[1]
F. Basic Oxidation
4 drops of the sample in a dry test
tube was added with a drop of 2% KMnO4
solution, 7 drops of distilled water and 3
drops of 10% NaOH solution. Each test tube
was warmed in a water bath for 2 minutes.
Any color change was observed.[1]
Results and Discussion
A. Physical State, Color and Solubility
Based on the observations, all six
samples were clear, colorless liquids at room
temperature that had strong, gasoline-like
odors. Hexane, heptane and cyclohexane
were
saturated
hydrocarbons
while
cyclohexene was an aliphatic unsaturated
hydrocarbon. Benzene and toluene were
aromatic hydrocarbons.

C. Ignition Test

B. Solubility in conc. H2SO4

Sulfuric acid reacts with both
alkenes and aromatic hydrocarbons,
although in different ways. Sulfuric acid
adds to cyclohexene via an acid catalyzed
addition. Sulfuric acid adds to toluene via
electrophilic aromatic substitution.[3] On
the other hand, alkanes are immiscible and
do not produce a reaction since all the bonds
are filled and there would be no room for the

sulfuric acid to attach or react to it.

Based on the results from the
experiment, only cyclohexene was miscible
with sulfuric acid. Both benzene and toluene
failed to yield results and just formed layers
which the group interpreted as miscible. The
lack of reaction may have been caused by
the contamination of the reagents, lack of
standing time or human error during the
procedure.

Generally, most hydrocarbons burn

over a flame- the hydrocarbons react with
oxygen to produce carbon dioxide and
water.[3] The number of carbon atoms in a
hydrocarbon only affected the sootiness
(production of CO2) of the flame. The
degree of luminosity remained the same but
compounds were produced at different
energies.
The results gathered showed that all
six samples were flammable. The first three,
hexane, heptane and cyclohexane produced
yellow flames without any soot. While the
following three, cyclohexene, benzene and
toluene produced yellow-orange flames with
soot.

The bromine test was another test

conducted to identify the actively
unsaturated hydrocarbons. Bromine, the
reagent used in the test, was an orangebrown aqueous solution that can only be
decolorized by alkenes. Bromine, when
added to alkanes and benzenes, would not
react since alkanes only react to bromine
under free radical conditions and benzenes
need a strong Lewis acid catalyst.[3]

D. Test for Active Unsaturation

a. Baeyers Test
Baeyers test was conducted to test
for the presence of active unsaturation. The
reagent used was KMnO4. Potassium
permanganate
reacts
with
anything
unsaturated. KMnO4 reacts with alkenes to
form vicinal diols. KMnO4 will also react
with alkyl benzenes, such as toluene, to
form benzoic acids. It does not react with
alkanes.[3] The compound that had a
positive reaction showed decolorization,
cyclohexene.

In the results gathered, it was

observed that only cyclohexene was able to
decolorize the reagent and produce a brown
precipitate. This indicated that among the
six samples only cyclohexane is an actively
unsaturated hydrocarbon.

E. Test for Aromaticity: Nitration

b. Bromine Test

Nitration is a chemical reaction in

which a nitro group is added to a
hydrocarbon compound replacing a
hydrogen. In nitration, sulfuric acid and
nitric acid, together served as the nitrating
mixture, was reacted with the samples. The
aromatic hydrocarbons react with warm
sulfuric acid to form a sulfonic acid which
will then dissolve and then precipitate when
the nitro group is precipitated.[3]

In the results, the yellow globules

indicated that the hydrocarbon was
aromatic which was observed for benzene
and toluene while the others that did not
produce any results were identified as
aliphatic.[4]

and it was assumed that they did not

undergo oxidation.[5]

In conclusion, it was observed that

the saturated hydrocarbons were hexane,
heptane and cyclohexane. The only actively
unsaturated hydrocarbon was cyclohexene
and that benzene and toluene are both
aromatic but only toluene may be classified
as an arene.

Sources
[1] (Bathan, et al., 2014, Laboratory Manual
in Organic Chemistry, pp. 81-84)
F. Basic Oxidation
In basic oxidation, a strong oxidizing
agent, KMnO4, was used. Its reaction to the
sample determined the presence of
oxidation.[6] A color change was the
indicator that the reaction between the
sample and oxidizing occurred. For this
experiment, there was an observed color
change in cyclohexene. The other five
samples showed no signs of decolorization

[2] Experiment 7: Classification Tests for

Hydrocarbons. (n.d.) retrieved November 20, 2015
from:
http://www.scribd.com/doc/37898377/Form
al-Report-Experiment-7-Classification-testfor-hydrocarbons
[3] Properties of Hydrocarbons (n.d.) retrieved
November
20,
2015
from:
http://www.mendelset.com/articles/689/prop
erties_hydrocarbons

[4] Aromaticity test: Nitration (n.d.) retrieved

November
20,
2015
from:
https://ph.answers.yahoo.com/question/inde
x?qid=20111119173932AAoWlxS
[5] (Poon, et. al., 2014, Introduction to Organic
Chemistry, pp. 305-308)
[6] Hydrocarbons and Its Identification Tests
for Classification (n.d.) retrieved November 20,
2015 from:
http://documents.mx/documents/hydrocarbons-andits-identification-tests-for-classification.html