CLASSIFICATION TESTS FOR HYDROCARBONS

Christine Dharryl F. Leal, Carl Nicanor V. Lontoc, Kristine Anne A. Mabansag, Janick Briand E.
Mallare, Justin Shaquille C. Manipon
Group 6 2F Medical Technology Organic Chemistry Laboratory
ABSTRACT
Hexane, heptane, cyclohexane, cyclohexene, benzene, and toluene were classified by observing their solubility,
flammability, active unsaturation, aromaticity, and oxidation to their specific tests. The physical properties of the
compounds were in clear liquid form, colorless, and varied in odor. The compounds were flammable and the alkanes
produced a yellow flame when subjected to the H 2SO4 and ignition test respectively. Decolorization from violet to
brown was seen only in cyclohexene in the reaction with 2% KMnO4 solution in the Baeyer's test. As for the Bromine
test composed of the reaction with 0.5% Br2 in CCl4 reagent, there was no change in benzene and toluene, while
immediate decolorization occurred in cyclohexene. Benzene and toluene appeared to be aromatic in the aromaticity
nitration test because both produced a yellow oily layer. The test for basic oxidation composed of the reaction with 2%
KMnO4 and 10% NaOH showed that cyclohexene changed from violet to brown, making it oxidized. The other
compounds did not undergo any change.

INTRODUCTION
Hydrocarbons are carbon compounds that can
be assigned as aliphatic hydrocarbons or as
aromatic hydrocarbons. Aliphatic hydrocarbons
which are saturated are alkanes, and closedchain hydrocarbons are named as a cycloalkanes.
If unsaturated, they can be an alkene or
cycloalkene,
alkyne
or
cycloalkyne.
[3]
Hydrocarbons may be saturated when carbon is
bonded to four other atoms through single
covalent bonds, therefore creating the maximum
number of hydrogens 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 Huckels Rule, their
structure is stabilized by resonance, and are all
cyclic. They undergo electrophilic substitution
reactions and nucleophilic aromatic substitutions.
[5]
In this experiment, different hydrocarbons
were to be tested according to their solubility,
flammability, active unsaturation, aromaticity,
and basic oxidation. Another objective was to
identify the different physical and chemical
properties of hydrocarbon compounds.

EXPERIMENTAL
A. Sample Used
Hexane, heptane, cyclohexane, cyclohexene,
benzene, and toluene were the hydrocarbon
compounds used in the experiment.

B. Procedure
1. Physical State, Color, Odor
The physical state and color of the compounds
were observed, and the odor was also sensed by
wafting or fanning the hands over the mouth of
the test tube.

2. Solubility in Concentrated H2SO4

One milliliter of conc. H2SO4 was applied to
a drop of each of the compounds in separate test
tubes by using calibrated droppers and change in
color and warming effect were observed right
after.

3. Ignition Test
3 drops of the liquid sample was placed in a
small evaporating dish and lighted with a match.
The sample was observed if it was flammable or
not. The color of the flame was also observed.

4. Tests for Active Unsaturation

The Baeyers test was done by the combination
of 5 drops of each of the compounds and 2 drops
of 2% KMnO4 solution. Bromine test was
performed by adding 10 drops of 0.5% Br 2 in CCl4
reagent to 5 drops of each compound. Shaking of
the test tube with the mixture was done
vigorously. If the mixture did not decolorize, it
must be exposed to sunlight.

5. Test for Aromaticity: Nitration

Preparation of the nitrating mixture must first
be accomplished by placing 2 ml of conc. HNO3 in
an Erlenmeyer flask and immersing it into water
from an evaporated dish, and conc. H2SO4 was
added gradually. Eight drops of the nitrating
mixture was added to 5 drops of each compound.
The mixture was diluted with water after shaking.
If no apparent reaction was seen, heat must be
applied by conducting a water bath that is not
more than 50C in 10 mins. Lastly, the mixtures
was diluted again with water.

6. Basic Oxidation
2% KMnO4 solution and 10% NaOH solution
with 8 and 3 drops respectively, were combined
to 4 drops of each hydrocarbon compound. The
mixture was warmed by a water bath for 2 mins.

Inference
D. Baeyers
Test

Bromine
Test

Inference
E. Test for
Aromatici
ty
Nitration
Inference

RESULTS AND DISCUSSION

Different tests like solubility in conc. H2SO4,
Ignition Test, Baeyers Test, Bromine Test, Test
for Aromaticity, and Basic Oxidation were
conducted to be able to differentiate and classify
the different hydrocarbon compounds.

Table 1. Results and Inferences

classification tests for hydrocarbons

Condensed
Structural
Formula
A. Physical
state at
RT
Color
Odor
B. Solubility
in
concentr
ated
H2SO4

Heptane

CH3CH2CH2
CH2CH2CH3

CH3CH2C
H2CH2CH
2CH2CH3

Clear liquid

Clear
liquid

Inference
C. Ignition
Test

Cyclohex
ane

Clear
liquid

Colorless

Colorless

Plastic
balloon

Chlorinelike

Alcohollike

Immiscible

Immiscib
le

Immiscibl
e

Flammable
No soot

saturate
d

saturated

Flammab
le
No soot

Flammabl
e
With soot

No
decoloriz
ation

No
decoloriza
tion

Positiveslow

Positiveslow

negative

Not
actively
unsaturate
d

Not
actively
unsatura
ted

Not
actively
unsaturat
ed

Clear oily
layer

Clear oily
layer

Clear oily
layer

Not
aromatic

Not
aromatic

Not
aromatic

No
decolorizat
ion

No
decoloriz
ation
Actively
saturate
d

No
decoloriza
tion

Cyclohex
e

Benzene

Toluene

Clear
liquid

Clear
liquid

Clear
liquid

Colorless

Colorless

Colorless

Gas-like

Gas-like

Rugby-like

Miscible
redbrown
mixture

immiscibl
e

immiscible

unsaturat
ed

unsaturat
ed

unsaturat
ed

Flammabl
e

Flammabl
e

Flammabl
e

With soot

With soot

With soot

Immediat
e
decoloriza

No
decoloriza
tion

No
decoloriza
tion

Actively
saturated

Actively
saturated

Condensed
Structural
Formula
A. Physical
state at
RT
Color

Colorless

saturated

Inference

of

Compounds Studied
Hexane

F. Basic
Oxidation

No
decolorizat
ion

Odor
B. Solubility
in
concentr
ated
H2SO4
Inference
C. Ignition
Test
Inference
D. Baeyers
Test

Bromine
Test

Inference

E. Test for
Aromatici
ty
Nitration
Inference
F. Basic
Oxidation

Inference

tion from
violet to
brown
Immediat
e
decoloriza
tion from
reddish
brown to
colorless

No
decoloriza
tion

No
decoloriza
tion

Actively
Unsaturat
ed

Not
Actively
Unsaturat
ed

Not
Actively
Unsaturat
ed

No color
change

Yellow
oily layer

Yellow oily
layer

Not
aromatic
Decoloriz
ation
from
violet to
brown
Actively
unsaturat
ed

Potassium permanganate did not react with the

alkane compounds tested because they are
saturated. When the reagent was added to
alkanes, the purple color does not change. [4]
Only cyclohexene gave out a reaction that
changed its color from violet to brown. Then it
may be concluded that cyclohexene was the only
actively unsasturated compound due to its
positive result against the reagents in Baeyers
Test.

Figure 1. Chemical reaction of alkene

in Baeyers Test
R

R
C

HO

+ 2KMnO
+ 2CH
OH
4
3

C
R

(purple)

OH
C

R
R

+ 2MnO
+ 2KOCH
2
3

aromatic

aromatic

(brown)

No
decoloriza
tion

No
decoloriza
tion

When KMnO4 solution was added to an alkene,

the purple color slowly disappeared and a brown
MnO2 precipitate formed. The appearance of the
brown precipitate indicate a positive test for
unsaturation.

Actively
saturated

Actively
saturated

Figure 2. Decolorization of alkene in

Baeyers Test

1. Physical State, Color, Odor

All of the hydrocarbon compounds tested
were in clear liquid state. They are all colorless
but they differ in odor. Hexane smelled like a
plastic ballon, heptanes as chlorine-like and
cyclohexane as alcohol-like. Cyclohexene and
benzene have both a gas-like odor, while toluene
was rugby-like.

2. Solubility in Concentrated H2SO4

All compounds were immiscible except
cyclohexene which had a miscible red-brown
mixture. Hexane, heptane, and cyclohexane are
saturated while cyclohexene, benzene, and
toluene are unsaturated.

3. Ignition Test
All of the compounds tested were flammable.
Thus, it can be inferred that all hydrocarbons are
combustible. The only difference seen was the
production of soot during the process. Only
hexane and heptanes did not have soot.

4. Tests for Active Unsaturation

Baeyers Test

A purple result was first produced by the

Baeyers Test for Unsaturation, this diluted into
light purple until it produced a brown precipitate
which indicated that the compound was already
unsaturated.
The bromine test was used to determine if the
colorless organic compounds contain any double
Carbon to Carbon bonds. Bromine did not react
with any alkane because the alkane has only
single C-C bonds which cannot add the bromine.
Alkanes merely dilute the red-brown bromine
color to an orange or yellow color in the absence
of a strong catalyst which was visible in the result
in hexane, heptane and cyclohexane. Due to their
C=C double bonds in cyclohexene, which can be
broken, alkenes react readily with bromine to
produce saturated dibromoalkanes. When an

alkene is reacted with bromine, the red-brown

color of the bromine is immediately lost due to
the reaction of the bromine. [4]

Aromatic compounds are extremely stable and

will not react without a catalyst so they act like
alkanes but are still unsaturated compounds.

Figure 3. Chemical reaction of alkene

in Bromine Test
R

R
C

UV light
+

Br2

Br
R

R
C

(reddish brown)

R
Br

(colorless)

Figure
4.
Chemical
reaction
aromatic compounds in nitration

of

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

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 no reaction
between the reagents, thus, the compound is
saturated. But, when the mixture was exposed to
sunlight, immediate decolorization took place,
wherein the orange solution became colorless,
which presented that the mixture was already
unsaturated.
Benzene and toluene are also alkenes but,
they are both aromatic that make them very
stable but also less reactive than cyclohexene
because their atoms are less available to be given
off. [6]

5. Test for Aromaticity: Nitration

A nitrite compound attached to benzene was

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]http://chemtech.org/cn/cn1105/experiments/
hydrocarbons.pdf
[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