CLASSIFICATION TESTS FOR HYDROCARBONS

Margarita Ysabel S. Mangahas, Cara Camille M. Matute, Emilyn D. Millares,

John Acener C. Padua and Kathryn Cheshire P. Pangilinan
Group 5 2A Medical Technology Organic Chemistry Laboratory

ABSTRACT
In the experiment, hydrocarbons were classified by observing their solubility, flammability, active unsaturation,
aromaticity, and oxidation to their appropriate and suitable tests. Hexane, heptanes, cyclohexane, cyclohexene,
benzene, and toluene were the hydrocarbon compounds studied. First, physical properties of the compounds were
observed to identify their physical state or phase, color and odor. All of the compounds were in clear liquid form and
are colorless, while they vary in odor. To test for solubility, concentrated H2SO4 or sulfuric acid was used as reagent.
Each of the compounds were tested according to their flammability by an ignition test. All of them were flammable
and the alkanes produced a yellow flame. In addition to that, only the cyclic compounds produced soot. Their active
unsaturation was also tested by using Baeyer’s test and Bromine test. In Baeyer’s test, the compounds reacted with
2% KMnO4 solution. Decolorization from violet to brown was seen only in cyclohexene. As for the Bromine test, the
compounds were studied through their reaction with 0.5% Br 2 in CCl4 reagent. It can be drawn from the results that
there was no change in benzene and toluene, while immediate decolorization occurred in cyclohexene. Moreover,
there was a slow reaction in hexane, heptane, and cyclohexane, but produced rapid reactions of turning to a colorless
solution under sunlight. Next, aromaticity of the hydrocarbons were tested. This was done by combining a nitrating
mixture composed of concentrated HNO3 and concentrated H2SO4 to the hydrocarbons. Heat was also applied to have
an apparent reaction. Aromatic compounds were found out to be benzene and toluene, by which both produced a
unique yellow oily layer. Lastly, test for basic oxidation was performed. In this test, the compounds reacted with 2%
KMnO4 and 10% NaOH. The only distinctive change was seen in cyclohexene which changed from violet to brown,
indicating that it is oxidized. The other compounds did not decolorize. [1]

INTRODUCTION The objectives of this experiment were to

Hydrocarbons are the simplest organic
compounds. They are Carbon compounds that
can be designated as aliphatic hydrocarbons or
as aromatic hydrocarbons. Aliphatic hydrocarbons
which are saturated are alkanes, and if found in a
closed-chain are named as a cycloalkane. If they
are unsaturated, they can be an alkene or
cycloalkene, alkyne or cycloalkyne. [5]
Hydrocarbons may be saturated which means
that each carbon is bonded to four other atoms
through single covalent bonds, thus it creates the
maximum number of hydrogen in a compound
due to the absence of any substituent. Hydrogen
atoms usually occupy all available bonding
positions after the carbons have bonded to each
other. While, unsaturated hydrocarbons contain
either double or triple bonds. Alkenes as
unsaturated compounds are also called olefins
and they form oily liquids on reaction with halides
like bromine gas. [2] Hydrocarbons may also be
aromatic compounds. They follow Huckel’s Rule,
their structure is stabilized by resonance, and are
all cyclic. They undergo electrophilic substitution
reactions and nucleophilic aromatic substitutions.
[3]
identify and classify the different hydrocarbons.
The hydrocarbons were to be tested according to
their solubility, flammability, active unsaturation,
aromaticity, and basic oxidation. To elaborate,
they were categorized and from the results were
inferred whether miscible or immiscible,
saturated or unsaturated, actively unsaturated or
not actively unsaturated, aromatic or not
aromatic, and oxidized or not. This experiment
also aim to identify the different physical and
chemical properties of hydrocarbon compounds.
EXPERIMENTAL
A. Sample Used
The samples used or compounds tested in the
experiment were hexane, heptane, cyclohexane,
cyclohexene, benzene, and toluene.
B. Procedure
1. Physical State, Color, Odor
The compounds were first observed to know
their physical properties. The state and color of
the compounds were observed, and the odor was
also sensed by wafting or fanning the hands
above the test tube.
2. Solubility in Concentrated H2SO4
 One milliliter of of conc. H2SO4 was applied to
a drop of each of the compounds in separate test Condensed CH3CH2C
CH3CH2CH2
tubes by using calibrated droppers, afterwhich, Structural H2CH2CH
CH2CH2CH3
Formula 2CH2CH3
change in color and warming effect were
observed.
A. Physical
3. Ignition Test Clear Clear
state at Clear liquid
Flammability of the compounds was tested by liquid liquid
RT
an ignition test. One by one, 3 drops of each of
the compounds were placed in an evaporating Color Colorless Colorless Colorless
dish and lighted with a match. Plastic Chlorine- Alcohol-
Odor balloon like like
4. Tests for Active Unsaturation
B. Solubility
Two different tests were done to analyze
in
active unsaturation of the compounds. The first Oily layer Oily layer Oily layer
concentr
test was the Baeyer’s test. This was done by the ated
combination of 5 drops of each of the compounds H2SO4
and 2 drops of 2% KMnO4 solution. Bromine test was Immiscib Immiscibl
Immiscible
performed by adding 10 drops of 0.5% Br2 in CCl4 Inference le e
reagent to 5 drops of each compound. Shaking of the C. Ignition Flammab Flammabl
mixture was done. If the mixture did not decolorize, it
Flammable
Test le e
must be exposed to sunlight. Yellow Yellow Yellow
5. Test for Aromaticity: Nitration Inference flame flame flame
Preparation of the nitrating mixture must first No No No
be accomplished by placing 2 ml of conc. HNO3 in D. Baeyer’s decolorizat decoloriz decoloriza
an Erlenmeyer flask and immersing it into water from Test ion ation tion
an evaporated dish, and conc. H2SO4 was added Fast
Fast Fast
gradually. Eight drops of the nitrating mixture was change
change change
added to 5 drops of each compound. The mixture was from
from from
diluted with water after shaking. If no apparent orange
orange to orange to
reaction was seen, heat must be applied by conducting Bromine to
colorless colorless
a water bath that is not more than 50°C in 10 mins.
Test colorless
under under
under
Lastly, the mistures was diluted again with water. sunlight sunlight
sunlight
6. Basic Oxidation Not Not Not
2% KMnO4 solution and 10% NaOH solution with 8 actively actively actively
and 3 drops respectively, were combined to 4 drops of Inference unsaturate unsatura unsaturat
each hydrocarbon compound. The mixture was d ted ed
warmed by a water bath for 2 mins. E. Test for
Clear oily Clear oily Clear oily
Aromatici
layer layer layer
RESULTS AND DISCUSSION ty
Different tests like solubility in conc. H2SO4, Nitration
Not Not Not
Ignition Test, Baeyer’s Test, Bromine Test, Test aromatic aromatic aromatic
Inference
for Aromaticity, and Basic Oxidation were
No No No
conducted to be able to differentiate and classify F. Basic
decolorizat decoloriz decoloriza
the different hydrocarbon compounds. Oxidation
ion ation tion
Not Not Not
Table 1. Results and Inferences of Inference
oxidized oxidized oxidized
classification tests for hydrocarbons Compounds Studied
Cyclohex
Benzene Toluene
Compounds Studied e
Cyclohex
Hexane Heptane
ane
 were in clear liquid state. They are all colorless
but they differ in odor. Hexane smelled like a
Condensed
plastic ballon, heptanes as chlorine-like and
Structural
Formula cyclohexane as alcohol-like. Cyclohexene and
benzene have both a gas-like odor, while toluene
was rugby-like.
A. Physical Clear Clear Clear 2. Solubility in Concentrated H2SO4
state at liquid liquid liquid Clear oily layer was the result in almost all
RT of the compounds except cyclohexene. A clear
Color Colorless Colorless Colorless orange oily layer was produced by cyclohexene
Rugby- with conc. H2SO4. These results indicate that
Odor Gas-like Gas-like
like cyclohexene are miscible and the others are
B. Solubility immiscible in conc. H2SO4.
in Orange Clear oily Clear oily 3. Ignition Test
concentr oily layer layer layer
All of the compounds tested were flammable.
ated
H2SO4 Thus, it can be inferred that all hydrocarbons are
Miscible Miscible Miscible combustible. The only difference seen was the
Inference production of soot during the process. Only the
C. Ignition Flammabl Flammabl Flammabl cyclohexene, benzene, and toluene had a soot
Test e e e wiye.
With soot With soot With soot 4. Tests for Active Unsaturation
Inference
Immediat Baeyer’s Test
e Potassium permanganate did not react with the
No No
decoloriza alkane compounds tested because they are
D. Baeyer’s decoloriza decoloriza
tion from saturated. When the reagent was added to
Test tion tion
violet to alkanes, the purple color does not change. [4]
brown
Only cyclohexene gave out a reaction that
Immediat
e changed its color from violet to brown. Then it
decoloriza No No may be concluded that cyclohexene was the only
Bromine
tion from decoloriza decoloriza actively unsasturated compound due to its
Test
reddish tion tion positive result against the reagents in Baeyer’s
brown to Test.
colorless
Not Not
Inference Actively Figure 1. Chemical reaction of alkene
Actively Actively
Unsaturat in Baeyer’s Test
Unsaturat Unsaturat
ed
ed ed R R HO OH

E. Test for C C + 2KMnO4 + 2CH3OH R C C R

Yellow Yellow Yellow
Aromatici R R R R
solution oily layer oily layer (purple)
ty + 2MnO2 + 2KOCH3
Nitration
Not Not Not (brown)

aromatic aromatic aromatic

Inference When KMnO4 solution was added to an alkene,
Decoloriza the purple color slowly disappeared and a brown
F. Basic No No
tion from MnO2 precipitate formed. The appearance of the
Oxidation decoloriza decoloriza
violet to brown precipitate indicate a positive test for
tion tion
brown
unsaturation.
Not Not
Inference Oxidized
oxidized oxidized
Figure 2. Decolorization of alkene in
1. Physical State, Color, Odor Baeyer’s Test
All of the hydrocarbon compounds tested
 The red aqueous layer as bromine, was used to
test the organic chemicals for a reactive carbon
double bond to decolourize the liquid. The
organic layer formed by cyclohexene,
decolourized the liquid slowly into orange
because cyclohexene contains a reactive double
bond. The reddish brown color of Bromine that
slowly diluted to orange indicated that there was
A purple result was first produced by the
no reaction between the reagents, thus, the
Baeyer’s Test for Unsaturation, this diluted into
compound is saturated. But, when the mixture
light purple until it produced a brown precipitate
was exposed to sunlight, immediate
which indicated that the compound was already
decolorization took place, wherein the orange
unsaturated.
solution became colorless, which presented that
The bromine test was used to determine if the
the mixture was already unsaturated.
colorless organic compounds contain any double
Benzene and toluene are also alkenes but,
Carbon to Carbon bonds. Bromine did not react
they are both aromatic that make them very
with any alkane because the alkane has only
stable but also less reactive than cyclohexene
single C-C bonds which cannot add the bromine.
because their atoms are less available to be
Alkanes merely dilute the red-brown bromine
given off. [6]
color to an orange or yellow color in the absence
of a strong catalyst which was visible in the result
5. Test for Aromaticity: Nitration
in hexane, heptane and cyclohexane. Due to their
Aromatic compounds are extremely stable and
C=C double bonds in cyclohexene, which can be
will not react without a catalyst so they act like
broken, alkenes react readily with bromine to
alkanes but are still unsaturated compounds.
produce saturated dibromoalkanes. When an
alkene is reacted with bromine, the red-brown
Figure 4. Chemical reaction of
color of the bromine is immediately lost due to
aromatic compounds in nitration
the reaction of the bromine. [4]

Figure 3. Chemical reaction of alkene

in Bromine Test
R R Br R
UV light
C C + Br2 R C C R

R R R Br
(reddish brown) (colorless)

A nitrite compound attached to benzene was

Due to their C=C double bonds in cyclohexene,
which can be broken, alkenes react readily with
bromine to produce saturated dibromoalkanes.
Figure 4. Decolorization of alkene in
Bromine Test
produced as seen in the chemical reaction of
benzene from a nitrating mixture composed of
conc. HNO3 and conc. H2SO4, and with aid of heat.
Nitrobenzene as well as p-nitrotoluene both gave a
yellow oily layer above a colorless solution. This
indicated that both compounds possess aromaticity.

6. Basic Oxidation
This test was done by using an inorganic
chemical compound, KMnO4 which is a strong
oxidizing reagent. An oxidation reaction occurred
in this test. Furthermore, NaOH had been used to
test if precipitate was to be formed. From the
results, only cyclohexene produced a change
wherein it decolorized from violet to brown. That
occurrence perceived that it is the only oxidized
compound.

REFERENCES
[1] Bayguen, A.V., et al. (2009). Laboratory
Manual in Organic Chemistry. Pearson Education,
Inc. pp 81-93

[2] http://www.elmhurst.edu/~chm/vchem
book/500hy drocarbons.html

[3] http://www.encyclopedia.com/topic/aromatic
_com pound.aspx#0-1E1:aromatic-full

[4] http://homepages.ius.edu/dspurloc/c122/hy
d.htm

[5] http://hyperphysics.phyastr.gsu.edu/hbase/
organic/hydrocarbon.html

[6] http://sciencephoto.com/media/4388/enla
rge