CLASSIFICATION TESTS FOR HYDROCARBONS

Judmel Acharon, Albert Alegre, Renee Andoy,

Jean Angelo, Alyssa Atos, Joie Ayuste
Group 1 2G-Medical Technology Organic Chemistry Laboratory

ABSTRACT
In the experiment, the organic compounds hexane, cyclohexane, cyclohexene, benzene, and toluene were used as
samples. The physical state, color and odor were noted by simple physical observation. The miscibility was tested by
adding a drop of the sample to about 1 ml of H 2SO4. The flammability was tested by placing 3-5 drops of the liquid
sample in a small evaporating dish and lighting it with a match. The active unsaturation was tested by using the
Baeyers and Bromine test and the aromaticity was determined by subjecting the samples to nitration. The oxidation
was tested by adding 1 drop of 2 % KMnO4 solution, 7 drops of distilled water, and 3 drops of NaOH solution to 4
drops of the sample in a test tube. All organic compounds showed immiscibility in concentrated H 2SO4 except for
cyclohexene. All showed flammability in the ignition test. All were not actively unsaturated except for cyclohexane.
Only benzene and toluene showed aromaticity. All but cyclohexene are not oxidized.

INTRODUCTION
Hydrocarbons are organic compounds that
contain only carbon and hydrogen atoms bonded
to each other. There are two carbon skeletons,
namely, acyclic which is open-chained and cyclic
which is closed chained. Hydrocarbons may be
divided into two classes namely : Saturated
hydrocarbons and Unsaturated hydrocarbons.
Hydrocarbons may also be aliphatic or aromatic.
Arenes are aromatic hydrocarbons that contain
alkyl side chains. Saturated hydrocarbons are the
simplest type of organic compounds. They are
hydrocarbons in which the carbon atoms in the
structure are bonded by single covalent bonds.
Unsaturated hydrocarbons are hydrocarbons that
contain double or triple bonds between carbon
atoms. Not all unsaturated hydrocarbons are
actively unsaturated.
The objective of the experiment is to differentiate
hydrocarbons in terms of intrinsic properties and
chemical properties based on structure and
behavior. It is also to analyze a hydrocarbon and
determine if it is saturated, actively unsaturated,
aromatic or an arene.

Fig. 1 (Saturated hydrocarbon)

g/mol, and a boiling point of 69 oC. Isomers of

hexane are mostly non reactive, and are
frequently used as solvents in organic reactions
because they are very non-polar. They are
common constituents of gasoline and leather
products.

Fig. 3 ( Structure of Hexane )

Cyclohexane is a cycloalkane with the
molecular formula C6H12, molar mass of 84.160
g/mol, and boiling point of 80.74oC. It is used as
a non-polar solvent and a raw material for the
production of adipic acid and caprolactam.
Cyclohexane is produced on an industrial scale by
reacting benzene with hydrogen.

Fig. 4 ( Structure of Cyclohexane )

Cyclohexene is a cycloalkene with a chemical
formula of C6H10, molar mass of 82.143 g/mol,
and a boiling point of 82.98 oC. It is not very
stable upon long term storage and exposure to
light and air should be distilled before use to
eliminate peroxides. It has a very sharp smell
resembling an oil refinery.

Fig. 2 (Unsaturated hydrocarbon)

EXPERIMENTAL
A. Compounds tested ( or Samples used )
Hexane is an alkane hydrocarbon with a
chemical formula of C6H14, molar mass of 86/18

Fig. 5 ( Structure of Cyclohexene )

Benzene is an organic chemical compound with

a molecular formula of C6H6, molar mass of
78.11g/mol, and a boiling point of 80.1C. It is a
colorless, highly flammable liquid with a sweet
smell. It is a known carcinogen, therefore its role
as an additive in gasoline is now limited, though
it is an important industrial solvent and a
precursor in the production of drugs, plastics,
synthetic rubber, and dyes.

was noted. It was compared with water as a

negative control. The decolorization of the
reagent is considered immediate if it occured
within a minute. The results were noted down.
b. Bromine Test
10 drops of 0.5% Br 2 in CCl4 reagent were
added to 5 drops of each of the samples in dry
test tubes. The test tubes were shaken vigorously
and the rate and extent (color change) by which
the reagent is immediately decolorized or when
the bromine color is discharged was observed. It
was compared with water as a negative control.
The reaction mixture was exposed to sunlight if
the reagent failed to decolorized within 1 minute.

Fig. 6 ( Structure of Benzene)

Toluene is an aromatic hydrocarbon with a
molecular formula of C7H8, molar mass of 92.14
g/mol, and a boiling point of 110.6C. Toluene
reacts as a normal aromatic hydrocarbon towards
electrophilic aromatic substitution. It is a waterinsoluble liquid with a smell of paint thinners, and
it is widely used as an industrial feedstock and
solvent.

5. Tests for Aromaticity: Nitration

2 ml of concentrated HNO3 was placed in an
Erlenmeyer flask. The flash was immersed in an
evaporating dish containing water. H2SO4 was
gradually added to the Erlenmeyer flask. The
resulting
mixture
was
cooled
to
room
temperature.
8 drops of the nitrating mixture was added to 5
drops of each of the samples in dry test tubes. It
was then shaken to ensure complete mixing. The
formation of yellow oily layer or droplet was
noted and then it was diluted with 20 drops of
water. If there is no apparent reaction observed
within a minute, the test tube was placed in a
water bath (~50oC) for 10 minutes. It was then
diluted with 20 drops of water. The results were
noted down.

Fig. 7 ( Structure of Toluene )

B. Procedure
1. Physical state, color, and odor
The physical state and appearance of the
sample
compounds
Hexane,
Cyclohexane,
Cyclohexene, Benzene, and Toluene were
observed at room temperature. The color and
order of each sample was noted.
2. Solubility in concentrated H2SO4
Using dry calibrated droppers, 1 ml of
concentrated H2SO4 was added to each of the
samples in the test tubes. The color change and
warming effects were noted.
3. Ignition Test
3-5 drops of the liquid sample were placed in a
small evaporating dish and was lighted with a
match. Any flame produced was noted.
4. Active unsaturation
a. Baeyer's test
2 drops of 2% KMnO 4 were added to 5 drops
of each of the samples in dry test tubes. The test
tubes were shaken vigorously and the rate and
extent at which the agent is decolorized was
observed. The formation of a brown suspension

6. Basic Oxidation
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 of the
samples in the test tubes. Each test tube was
warmed in a water bath for 2 minutes and any
color change in the solution was observed.

RESULTS AND DISCUSSIONS

After subjecting all 5 organic samples to
different physical and chemical tests, it was then
observed that all showed immiscibility except in
concentrated H2SO4 except for cyclohexene. All
showed flammability in the ignition test. All were
not actively unsaturated except for cyclohexane.
Only benzene and toluene showed aromaticity. All
but cyclohexene are not oxidized.

Physical
state
Appear..
Color
Odor

Hexane

Cyclohexane

Cyclohexene

Liquid

Liquid

Liquid

Clear
Colorles
s
Rubber
like

Clear
Colorless

Clear
Colorless

odorless

LPG-like

Benzene

Toluene

Liquid
Liquid
Apperance
Clear
Clear
Color
Colorless
Colorless
Odor
Marker-like
Gas-like
Figure
8.
(Physical
State
at
Room
Temperature)
Physical state

Hexane

Sol.
in
H2SO4
Inferenc
e

Immiscible
Not actively
unsaturate
d

Sol. in H2SO4
Inference

Cyclohexan
e
Immiscible

Cyclohexen
e
Miscible

Not actively
unsaturated

Actively
unsaturated

Toluene
Immiscible
Not
actively
unsaturated

Figure 9. (Solubility in concentrated H2SO4)

Ignition
test
Inferenc
e

Flammabl
e
w/ yellow
flame

Ignition Test
Inference

Cyclohexan
e
Flammable

Cyclohexene

Non-luminous
blue flame

Toluene
flammable
Luminous,
yellow flame

Figure 10. (Ignition Test)

Baeyer's
Test

No
decolorizatio
n

Bromine
Test

No
decolorizatio
n
Not actively
unsaturated

Inferenc
e

Baeyer's Test
Bromine Test

Not
actively
unsaturated

Figure 11. (Tests for active unsaturation)

Hexane
Nitration

Inference

Colorless
sol'n w/
oily layer
Not
aromatic

Cyclohexan
e
Colorless
sol'n w/ oily
layer
Not aromatic

Benzene
Yellow oily layer
aromatic

Nitration
Inference

Cyclohexan
e
Violet
to
brown sol'n

Colorlessorange sol'n
Actively
unsaturated

Benzene
No
decolorization
Slow
decolorization

Hexane
Basic
oxidatio
n
Inferenc
e

No
decolorizatio
n
Not oxidized

Flammable

w/
orangeyellow flame

Benzene
Flammable
Luminous,
orange flame

Hexane

Not
actively
unsaturated

Cyclohexen
e
Black sol'n

Not aromatic

Toluene
Yellow oily layer
Aromatic

Figure 12. (Tests for aromaticity nitration)

Benzene
Immiscible
Not
actively
unsaturated

Hexane

Inference

Cyclohexen
e
Violetbrown, imm
presence or
brown ppt.
Slow
decolorizatio
n
Not actively
unsaturated

Toluene
No
decolorization
Colorless=yellow
Immediate
decolorization

Basic Oxidation
Inference

Cycohexan
e
No
decolorizatio
n
Not oxidized

Benzene
No
decolorization
Not oxidized

Cyclohexen
e
Violet
sol'n
to
brown
ppt.
Oxidized

Toluene
No
decolorization
Not oxidized

Figure 13. (Basic Oxidation)

REFERENCES
From books
University of Santo Tomas Faculty of Pharmacy.
(2014). Laboratory Manual in Organic Chemistry
Revised Edition. Manila: Author
From the internet (on-line)
http://spmchemistry.onlinetuition.com.my/2013/
01/hydrocarbon.html
http://www.chem.latech.edu/~deddy/chem121/A
lkanes.htm
https://en.wikipedia.org/wiki/Cyclohexane
https://cornellbiochem.wikispaces.com/Hexane
http://chemistry.stackexchange.com/questions/1
8468/is-the-kekule-structure-of-benzenecompletely-wrong
https://en.wikipedia.org/wiki/Toluene_toxicity