UNIVERSITY OF SANTO TOMAS

FACULTY OF PHARMACY
Organic Chemistry Laboratory
A.Y. 2018-2019

Experiment no. 7
Classification Tests for Hydrocarbons
Calugay, J.J., Caparas, C.E., Dador, A.S., De Guzman, D., & De Villa, G.K.

Abstract
In this experiment, some organic compounds were put to various physical tests to
identify ​their intrinsic physical properties and various chemical tests as well to
determine their ​chemical properties in terms of their structure and behaviour. ​Hexane,
heptane, cyclohexane, cyclohexene, benzene and toluene were the samples used for
this experiment. First, the physical state, color, odor and the appearance of each
sample were observed in room temperature. To determine their miscibility in H​2​SO​4​, a
drop of each and every sample was added to about 1 mL of concentrated H​2​SO​4​,
separately. Changes in color of the mixture and warming effect/s were noted. The
flammability of each organic compound was determined as well. Ignitions tests were
performed by ​placing 3-5 drops of each sample to a small evaporating and then lighting
it with a match. ​2 drops of 2% KMnO​4 ​solution was added to 5 drops of each sample to
conduct the Baeyer’s test. Formation of any brown suspension was observed. The
decolorization of the reagent if it occurred within 1 minute was also noted. ​The test ​for
aromaticity of each com​pound was determined through the process of ​nitration​. The
miscibility of every organic compound was identified by mixing 8 drops of the nitrating
mixture to 5 drops of each sample. Formation of yellow oily layer or droplet was noted.
Each mixture was then diluted with 20 drops of water and then placed in a water bath
for 10 minutes. It was then again diluted to 20 drops of water, after which, results were
noted. Lastly, test for basic oxidation was conducted. 1 drop of 2% KMnO​4 solution, 7
drops of distilled water, and 3 drops of 10% NaOH solution were added to 4 drops of
each sample. Then, the test tubes were warmed in a water bath for 2 minutes, after
which, changes in color of the solution were observed.
Introduction
Hydrocarbon compounds are the heptane, cyclohexane, cyclohexene,
simplest types of organic compounds. benzene, and toluene.
These compounds contain hydrogen
atoms and carbon atoms bonded
together. For classification purposes,
hydrocarbon compounds can be
designated as aliphatic hydrocarbons or
as aromatic hydrocarbons depending on
how the atoms are connected.
Aliphatic hydrocarbons may be acyclic or
(Figure 1. Hexane)
cyclic. Acyclic compounds are carbon
atoms in either single or branched
chain, while cyclic compounds have
carbon atoms linked in a closed ring or
polygon. Another hint for classifying
Aliphatic hydrocarbons depend on
saturation. Aliphatic hydrocarbons that
contain only sigma bonds are called
saturated hydrocarbons and those
(Figure 2. Heptane)
containing both sigma and pi bonds are
called unsaturated hydrocarbon.
Aliphatic hydrocarbons are divided into 3
classes: alkanes are saturated
hydrocarbons that contain only
carbon-carbon single bonds. Alkenes are
unsaturated hydrocarbons that contain
at least one carbon-carbon double bond.
Alkynes are unsaturated hydrocarbons
that contain at least one carbon-carbon
(Figure 3. Cyclohexane)
triple bond.
On the other hand, Aromatic
hydrocarbons can be identified if they
are cyclic, planar, or if it follows Huckel’s
rule (4n+2 = πe).
There were 6 sample organic
compounds used, namely: hexane,
 (Figure 4. Cyclohexene)
(Figure 5. Benzene)
(Figure 6. Toluene)
Various tests were performed to identify
the properties of the compounds as to
differentiate them if the sample organic
compounds are hydrocarbons or not,
including its properties such as
saturation, flammability, miscibility, and
etc.
The first test was done to determine the
drugs miscibility in Concentrated H2SO4.
Miscibility is the property of liquids to to
mix in all proportions, therefore forming
a homogeneous solution.
The second test performed was ignition
test to determine flammability and
luminosity. It also determine the degree
of saturation. The degree of luminosity
can be assessed by the presence of
yellow flame and soot.
Baeyer’s test is a test for unsaturation
or double bonds. Baeyer’s test uses a
solution called the Baeyer’s reagent. A
positive result which is actively
unsaturated leads to a result of
decolorization of a purple solution and
formation of a brown precipitate.
Bromine test, like Baeyer’s test, is a test
for double bonds and aromatic
compounds. The reagents used are
0.5% Br2 in CCl4. A positive result
shows decolorization of an orange
solution.
Test for Aromaticity is determined
through Nitration. The reagents used
are HNO3, H2SO4. A positive result
shows a yellow oily layer.
The last test performed was Basic
Oxidation, a test for alkylated aromatics
or arenes. There agents used were 2%
KMnO4 and 10% NaOH. A positive
result in the test leads to a violet
solution (MnO4) or brown precipitate
(MnO2).
Methodology
The materials used were test tubes, test
tube holder and rack, small and big
evaporating dishes, erlenmeyer flask,
beaker, droppers, distilled water, 10%
NaOH solution, 2% KMnO​4 solution,
concentrated H​2​SO​4 and HNO​3​. Sample
compounds used were hexane, heptane,
cyclohexane, cyclohexene, benzene, and
toluene.
 4. Test for Active Unsaturation:
Baeyer’s Test
5 drops of the sample was placed in a
dry test tube. 2 drops of 2% KMnO​4
solution was added. The test tube was
shaken vigorously and the rate and
extent at which the reagent was
decolorized was observed. Formation of
any brown suspension was observed.
The immediate decolorization of the
reagent if it occurred within 1 minute
Fig 7​. Hydrocarbons
was also noted.

1. Physical State, Color, and Odor

First, physical state and the appearance
of each sample were observed in room
temperature. Color and odor were also
described.
2. Solubility in Concentrated H​2​SO​4
A drop of the sample was cautiously
added to about 1 mL of concentrated
H​2​SO​4 using dry droppers. Same
Fig 8​. Addition of 2% KMnO​4
procedure was done for every sample.
Color changes and/or warming effects 5. Test for Aromaticity: Nitration
were noted and solubility for each was
2 mL of concentrated HNO​3 was placed
described.
in an erlenmeyer flask. The flask was
3. Ignition Test immersed in an evaporating dish
containing water and 2 mL of
3-5 drops of the sample was placed in a
concentrated H​2​SO​4 was gradually
small evaporating dish and lighted by a
added. The resulting mixture was cooled
match. The sample was observed if it is
to room temperature and served as the
flammable or not and if there was a
nitrating mixture. Then, 5 drops of the
formation of soot. For flammable
sample was placed in a dry test tube. 8
compounds, burning time was also
drops of the nitrating mixture was
observed. This was repeatedly done for
added and the test tube was shaken to
all samples.
ensure complete mixing. Formation of
yellow oily layer or droplet was noted.
The mixture was then diluted with 20
drops of water. Same procedure was A.Physical State at room
done for every sample. For compounds temperature and Appearance
with no apparent reaction observed
within 1 minute, the test tube/s was Sample Physical Appearance
placed in a water bath (~50℃) for 10 State at
minutes. Then it was diluted with 20 RT
drops of water. Results were noted. hexane liquid Clear solution
6. Basic Oxidation heptane liquid Clear solution
4 drops of the sample was placed in a
cyclohexane liquid Clear solution
test tube 1 drop of 2% KMnO​4 solution,
7 drops of distilled water, and 3 drops of cyclohexene liquid Clear solution
10% NaOH solution were added. Same
procedure was done for every test tube. benzene liquid Clear solution
Then, the test tubes were warmed in a toluene liquid Clear solution
water bath for 2 minutes. Color changes
Table 1. Physical State at RT and Appearance of
in the solution were observed. Hydrocarbons

Color and Odor

Sample Color Odor

hexane Colorless petroleum-

like odor

heptane Colorless mild,

bubble-like
odor

Fig 9.​ Water bath cyclohexane Colorless detergent-

like odor
Results
cyclohexene Colorless sweet odor
The obtained results from the
experimentation were represented by benzene Colorless sweet/
the tables below aromatic
odor

toluene Colorless strong,

rugby-like
odor
Table 2​. Color and Odor of hydrocarbons
Tables 1 and 2 presented the Physical C. Ignition test
state at room temperature, appearance,
color, and odor of ​hexane, heptane, Sample Ignition Inference
cyclohexane, cyclohexene, benzene, and test
toluene. These physical states can be hexane no soot, Flammable,
observed and determined immediately. yellowish, saturated
All the hydrocarbons are liquid, have 10.83s
clear appearances, and colorless. They
also have their own odor which made heptane no soot, Flammable,
them distinguishable. yellowish, saturated
B. Solubility in concentrated 12.42s
Sulfuric acid cyclohexane no soot, Flammable,
20.53s saturated
Sample Solubility Inference
in H​2S
​ O​4
cyclohexene with visible Flammable,
hexane Immiscible not weak soot, unsaturate
base 17.83s d
heptane Immiscible not weak benzene with visible Flammable,
base soot, unsaturate
16.50s d
cyclohexa Immiscible not weak
ne base toluene with visible Flammable,
soot, 8.12s unsaturate
cyclohexe turned weak base d
ne orange,
miscible Table 4.​ Ignition test for hydrocarbons

Table 4 showed results for the ignition

benzene miscible weak base
test of the hydrocarbons. Hexane,
toluene turned pale weak base heptane, and cyclohexane were
yellow, flammable but there were no observed
miscible soot. Thus, they are saturated. While
Table 3.​ Solubility of Hydrocarbons in Concentrated Sulfuric cyclohexene, benzene, and toluene were
Acid
also flammable, but all three produced a
Table 3 showed the solubility of visible soot. Thus, they are unsaturated.
hydrocarbons in concentrated sulfuric The test was performed to indicate the
acid. This test is used to determined if presence of unsaturation. Generally,
the hydrocarbon is a weak base. The higher carbon to hydrogen ratio equals
dissolution of compounds in ​H2​​ SO​4 ​may high luminosity and the more the flame
also produce a change in color. Thus, smoke or soot produced.
based on the results, cyclohexene,
benzene, and toluene are weak bases.
D. Baeyer’s test

Sample Result Inference

hexane No saturated
decolorization

heptane No saturated
decolorization

cyclohexane No saturated
decolorization

cyclohexene Immediate unsaturated

decolorization​,
Fig 10.​ Results for Baeyer’s test
changed to
brown color

benzene decolorized unsaturated E. Test for aromaticity nitration

toluene decolorized unsaturated Sample Result Inference

Table 5.​ Baeyer’s test result and inference
hexane formation of not
Table 5 showed the results of the clear oily aromatic
Baeyer’s test, which is used to identify layer
unsaturation or the presence of double
heptane formation of not
bonds or triple bonds. The results
clear oily aromatic
showed that cyclohexene, benzene and layer
toluene reacted with the potassium
permanganate because of the cyclohexane formation of not
decolorization. Thus, they are clear oily aromatic
unsaturated. While hexane, heptane, layer
and cyclohexane does not decolorized, cyclohexene formation of not
thus, they are saturated. clear oily aromatic
layer

benzene formation of aromatic

yellow, oily
layer

toluene formation of aromatic

yellow, oily
layer
Table 6.​ Test for aromaticity nitration
Table 6 showed the results for nitration water bath for two minutes.
test which is used to identify the Decolorization or formation of
aromatic hydrocarbon/s. An aromatic precipitate means that the hydrocarbon
hydrocarbon is identified with the was oxidized. Based on the results;
formation of a yellow, oily layer. Based hexane, cyclohexane, benzene, and
on the results, benzene and toluene are toluene were oxidized. While heptane
aromatic because they formed a yellow, and cyclohexene did not.
oily layer. While the rest are not
aromatic.

F. Basic Oxidation

Sample Result Inference

hexane decolorized, oxidized,

changed to arene
light brown

heptane no no
decolorization oxidation

cyclohexane decolorized, oxidized,

Fig 11.​ Results for the Oxidation test
changed to arene
blue-green Discussions

cyclohexene no no In this experiment, different

decolorization oxidation hydrocarbons were subjected to various
tests whether to know the properties
benzene decolorized, oxidized, they possess or acquire. These
changed to arene hydrocarbons are hexane, heptane,
blue-green cyclohexane, cyclohexene, benzene and
toluene.
toluene decolorized, oxidized,
changed to arene All hydrocarbons appeared as a clear
dark liquid solution. Their odor varied from
blue-green hexane having a petroleum like odor,
Table 7. ​Results for the basic oxidation test
heptane with a mild- bubble like odor,
cyclohexane with detergent odor,
Table 7 showed the results for the basic cyclohexene and benzene with a sweet
oxidation test; which is used to test the odor and toluene with strong rugby like
presence of alkylated aromatics or odor.
arenes after the addition of reagents; For the solubility in H​2​SO​4 ,​ hexane,
2% KMnO​4 ​and 10% NaOH to the heptane and cyclohexane are immiscle
hydrocarbons and their subjection to and not considered a weak base while
cyclohexene, toluene and benzene are
miscible in​ ​H​2​SO​4.
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 Ignition Test was done and all
hydrocarbons had put up flame once
tested but only cyclohexene, benzene
and toluene had soot after flame
duration.
Baeyer’s test is used to identify the
presence of double or triple bonds in a
hydrocarbons (unsaturation). The
reagent used was Potassium
Permanganate and a positive result
should decolorized the purple solution
into a brown solution. Cyclohexene,
benzene, and toluene showed positive
result, thus, they are unsaturated.
In the test for aromaticity nitration,
hydrocarbons formed an oily layer
however benzene and toluene formed a
yellow oily layer. Thus they are
unsaturated.
The basic oxidation test was also used
to and heptane and cyclohexene gave
no results while hexane decolorized to
brown, cyclohexane, benzene and
toluene decolorized to blue green.
Based from all of the tests done,
different hydrocarbons gave results to
classify their saturation and aromaticity.
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