Classification Tests for Hydrocarbons

2BMT, Group No. 2, Bandilla, K.D., Cao, S.J.C.*, Clarito, M.A.N., Co, J.J.A.,
Cruz, R.J.E., and Dacquiado, P.D.E.
Department of Pharmacy, Faculty of Pharmacy, University of Santo Tomas,
Espaa Boulevard, 1015 Manila, Philippines
ABSTRACT
Hydrocarbons are the simplest organic compounds consisting of only carbon atoms and
hydrogen atoms. Classification tests were done to determine the different properties of the given
liquid hydrocarbon sample namely: hexane, heptane, cyclohexane, cyclohexene, benzene, and
toluene. Solubility in concentrated sulfuric acid (H2SO4) was observed in cyclohexene. All liquid
samples were found to be flammable and there was no soot in both hexane and heptane. Only
cyclohexene was found out to be actively unsaturated and it was confirmed through Baeyers
test and Bromine test. It was confirmed through nitration test that both benzene and toluene
were aromatic compounds and the rest of the samples were aliphatic. Lastly, toluene was
confirmed to be an arene and this was done through basic oxidation.
INTRODUCTION

The objectives of this experiment

Hydrocarbons

are

the

simplest

were: (1) To differentiate hydrocarbons in

organic compounds which only have carbon

terms of intrinsic physical properties; (2) To

atoms and hydrogen atoms in its structure,

differentiate chemical properties bases on

covalently bonded together. The structure

structure and behavior; and (3) To analyze a

can be acyclic or cyclic. It can also be

hydrocarbon and determine if it is saturated,

aliphatic or aromatic, and those aromatic

actively unsaturated, aromatic, or an arene.

hydrocarbons with alkyl substituents are

called

arenes.

In

addition,

there

METHODOLOGY

hydrocarbons can be saturated, unsaturated

In this experiment, a total of seven

or actively unsaturated based on the

(7) classification tests were made to six (6)

presence of the number of bonds in the

different hydrocarbons namely: hexane,

structure.

heptane,

The classifications of hydrocarbons

are made to differentiate the different

cyclohexane,

cyclohexene,

benzene, and toluene.

A. Physical State, Color, and Odor

properties of the compounds. In doing so, it

The six (6) samples were placed in

is easily determined if the given sample is

different test tubes and the samples

an alkane, alkene, aromatic or an arene, or

were observed for the physical state at

easily determined if it is saturated or

room temperature, and the color. For the

unsaturated based on this experiment.

odor, wafting motion of the hands to the

nose was done since direct smelling of

the samples is a laboratory precaution

D. Test

for

Active

Unsaturation:

and it should not be done in doing

Baeyers Test

experiments.

Five (5) drops of the samples were

place in different test tubes. Two (2)

B. Solubility in Concentrated H2SO4

Sulfuric

acid

is

corrosive,

dehydrating, and reacts violently with

water, extra precaution was observed.
To one (1) mL of the concentrated

drops of 2% potassium permanganate

(KMnO4) solution was added, then
shook vigorously. The rate and extent of
the decolorization of the reagent was
observed.

H2SO4, added cautiously was one (1)

drop oe the samples to different test
tubes.

While

adding

the

sample,

Formation of a brown suspension

was also observed, and was compared
with water as a negative control.

observations for any color change and

any warming effect were observed.
The results in the solubility property
were reported as immiscible or miscible.
Neutralization of the solution was
made by adding few drops of 10%
sodium hydroxide (NaOH), then the
neutralized solution was placed in the

Immediate

decolorization

was

recorded if it occurs within one (1)

minute, else it is slow decolorization. No
change can also be observed. Other
observations

were

also

recorded.

Inference was said to be actively

unsaturated or not actively unsaturated
depending on the results.

organic compounds container.

E. Test
C. Ignition Test

Afterwards, it was lit by a match.

Observations of a flame and formation
of soot were done. In addition to that,
burning time was also recorded.
Results were recorded as flammable

the sample is flammable.

Unsaturation:

Five (5) drops of the samples were

placed in different test tubes. 10 drops
of

0.5%

bromine

(Br2)

in

carbon

tetrachloride (CCl4) reagent was added,

then shook vigorously to immediately
decolorized or discharge the bromine
color.

or not flammable, or with or without

formation of soot plus the burning time if

Active

Bromine Test

Five (5) drops of the liquid samples

were placed in an evaporating dish.

for

The solution is placed under sunlight

to

further

facilitate

the

immediate

decolorization of the solution. Water was

used

as

negative

control

for

comparison.

bath for 10 minutes. Afterwards, dilution

with 20 drops of water was done.

Results were recorded as immediate

Before disposing the solutions used,

decolorization if it occurs within one (1)

they were slowly diluted in 20 mL of

minute.

water then sodium carbonate was added

No

change

can

also

be

observed. Other observations were also

recorded. Inference was said to be

until foaming ceases.

The

color

of

the

solution

was

actively unsaturated or not actively

recorded. Inference was said to be

unsaturated depending on the results.

aromatic or not aromatic depending on

the results.

F. Test for Aromaticity: Nitration

Nitrating mixture was first made by

G. Basic Oxidation

placing two (2) mL of concentrated nitric

Four (4) drops of the samples were

acid (HNO3) in an Erlenmeyer flask. The

placed in different test tubes. One (1)

flask was immersed in an evaporating

drop of 2% potassium permanganate

dish containing water and two (2) mL of

(KMnO4) solution, seven (7) drops of

concentrated sulfuric acid (H2SO4). The

distilled water, and three (3) drops of

mixture is cooled to room temperature

10% sodium hydroxide (NaOH) solution

afterwards.

is

were added to the samples. These test

corrosive, dehydrating, and violently

tubes were warmed in a water bath for

reacts with water, while concentrated

two (2) minutes. Color change in the

HNO3 is corrosive and oxidizing, so

solution was observed.

Concentrated

H2SO4

extra precaution was made in doing the

nitrating mixture.
Five (5) drops of the samples were
placed in different test tubes. Eight (8)

Results were recorded as the color

change

observed

or

no

change.

Inference was said to be oxidized or not

oxidized depending on the results.

drops of the nitrating mixture was

added, then the test tube was shook to

RESULTS AND DISCUSSIONS

ensure complete mixing. Formation of a

Results

yellow oily layer was observed, then

Results are placed after the Discussions

dilution with 20 drops of water was

section of this study

done.
The test tubes without any reaction

A. Physical State, Color and Odor

observed was placed in the 50 C water

3

All six (6) samples were liquid and

Changes in cyclohexene and toluene

colorless in room temperature. The odor of

were

hexane was plastic balloon-like, odor of

colorless while the latter became turbid.

heptane

Only cyclohexene was recorded to be

was

chlorine-like,

odor

of

cyclohexane is alcohol-like, odor of both

observed.

The

former

became

actively unsaturated.

cyclohexane and cyclohexene were gaslike, and odor of toluene was rugby-like.
B. Solubility in Concentrated H2SO4
All six (6) samples were found out to be
insoluble in concentrated H2SO4. Oily layer

F. Test for Aromaticity: Nitration

Changes in cyclohexene, benzene and

formation was also observed: oily layer for

toluene

hexane;

heptane,

formed a black precipitate after adding the

cyclohexane, and toluene; orange oily layer

nitrating mixture, while both benzene and

for cyclohexene, and; translucent oily layer

toluene formed a yellow oily layer. Benzene

for benzene.

and toluene were recorded to be aromatic.

clear

oily

layer

for

were

observed.

Cyclohexene

C. Ignition Test

G. Basic Oxidation

All six (6) sample were found out to be

Only cyclohexene was observed to have

flammable but with different burning time.

a change as it became black during the

There was no soot formation for both

process, and it was also recorded to be

hexane and heptane while the rest formed

oxidized.

soot.
Discussions
D. Test

for

Active

Unsaturation:

Baeyers Test
Changes

in

All six (6) samples were the same

with regards to their physical state and color

cyclohexane

and

cyclohexene were observed. The former

became turbid and brown, while the latter

in room temperature. Distinct odors were

observed in each sample.
As

shown

in

the

results,

the

became brown in immediate decolorization.

cyclohexene was the only compound that

Only cyclohexene was recorded to be

showed a distinct coloration in one of its

actively unsaturated.

layer. Mixing the solution of cyclohexene

and concentrated H2SO4 should make it

E. Test

for

Bromine Test

Active

Unsaturation:

miscible since the addition of concentrated

H2SO4 should form an alkyl hydrogen

sulfate. Benzene and toluene can be

shown a non-luminous flame. Complete

miscible in concentrated H2SO4 if there is a

combustion occurs when there is sufficient

presence of sulfur trioxide (SO3). As for

oxygen fueling the fire while incomplete

hexane, heptane and cyclohexane, they

combustion occurs when there is insufficient

cannot interact with concentrated H2SO4

oxygen.

with their single bond structure.

CxHy + O2 CO2 + H2O

CxHy + O2 CO + C + H2O
Figure 2. General Equations of Combustion.
Top:
Figure 1. General Electrophilic Addition of

in H2SO4 can indicate whether the sample is

a very weak base or a neutral compound.
Alkene is included in the very weak base
list. Distinct changes in the solution maybe
large amount of heat being released, a
change in the color of solution, precipitation,
or any combination of these changes.
All six (6) samples were found out to
be flammable but with different burning time,
and different in the formation of soot. The
ignition test can find out whether the given
sample is unsaturated or high carbon to
hydrogen ratio. As you increase the C-H
ratio, the flame becomes more luminous
and flame becomes sootier. A sooty flame is
caused by incomplete combustion of the
compound. The soot is caused by unburned
carbon. The samples without soot (hexane
and heptane), completed combustion and

Combustion;

Bottom: Incomplete Combustion

Sulfuric Acid to an Alkene

The solubility of organic compounds

Complete

The Baeyers test is a test for the

presence of unsaturation. An unsaturated
compound is defined to have a double bond
or a triple bond in its structure, else it is a
saturated compound.
The positive result should be the
decolorization of the purple color of KMnO 4
and an appearance of a brown suspension
(MnO2). In the results, only the cyclohexene
reacted. This is because, alkenes and
alkynes are the ones which can react on the
KMnO4. Adding water after the reaction with
KMnO4 will result to diols. Reaction of
KMnO4

in

alkanes

(such

as

hexane,

heptane, and cyclohexane) cannot happen

because they are already saturated. This is
the same with aromatic hydrocarbons (such
as benzene and toluene) because of their
stability.

The

Baeyers

test

involves

reduction-oxidation reaction, as Mn7+ is

reduced to Mn4+. Because the cyclohexene

was the only compound that reacted to

aromatic if all carbon atoms in the ring are

KMnO4, it is actively unsaturated.

sp2-hybridized, has resonance structure,

and follows the Huckels Rule (4n + 2). If
one condition is not met, it is said to be
aliphatic already.
The positive result for Nitration test
is the presence of a yellow globule or a
yellow layer which were present in both

Figure 3.

benzene and toluene, since seeing their

The Baeyers Test Reaction for Alkenes

structure, they have the benzene ring, an

aromatic organic compound. The principle

The Bromine test is also another test

for the presence of unsaturation. The
positive result should be the decolorization
of

the

orange

solution.

Only

the

cyclohexene reacted with the bromine

solution since it can make the unsaturated
compound

to

saturated

one

by

electrophilic addition. Alkanes (such as

behind nitration is also because of aromatic

electrophilic substitution. One hydrogen
atom in the benzene ring will be replaced by
the

undergo electrophilic addition, rather it will

undergo radical substitution, but still alkanes

nitronium

ion

(NO2:+)

present in the nitric acid. Because of this

reaction. Benzene will react to become
Nitrobenzene, and toluene will react to
become o-nitrotoluene or p-nitrotoluene.

hexane, heptane, and toluene) can react to

bromine under ultraviolet light but it will not

electrophile,

Although cyclohexene produced a

black precipitate, it is still an aliphatic
organic compound since the positive result
should be a yellow solution and not a black

are saturated in this reaction. The aromatic

compounds (such as benzene and toluene)
will only react in the bromine solution with
the presence of FeBr3 or through ultraviolet
light.

precipitate.

Figure 4. Electrophilic Addition of Bromine

Figure 5. Nitration of Benzene

to Alkenes
Basic Oxidation is a test for the
Nitration test is a test whether the
given organic compound is aromatic or
aliphatic. An organic compound is said to be

present of an alkylated aromatic compounds

or

arenes.

Oxidizing

these

kind

of

compounds with strong oxidizing agents will

convert

the

of an oxidation reaction to confirm the

alkyl part of

presence of arene, inferring that it should be

the ring to a

not be oxidized. Cyclohexene could have

This

undergone oxidation if it is to be in an acidic

conversion of an alkylbenzene into a

environment, but for this nitration, sodium

benzoic acid.

hydroxide (NaOH) was added to have a

carboxyl

group,

-COOH.

is

The positive result of this test should

basic environment.

be a green solution, made by the KMnO 4,

Just like the Baeyers test, basic

and a brown precipitate, the MnO 2. Results

oxidation

is

also

reduction-oxidation

were not observed by the correct organic

reaction as the Mn7+ is reduced to Mn6+ or

compound, toluene, since it is the only one

Mn4+ depending on the extent of the

that is an aromatic compound with an alkyl

reaction.

group. It should be noted that black color

Figure 6. Oxidation of Toluene

observed in cyclohexene is not an indication

Condensed
Structural
Formula
A. Physical
State in RT
Appearanc
e
Color
Odor
B. Solubility
in conc.
H2SO4
Inference
C. Ignition
Test
Inference
D. Baeyers
Test
Bromine
Test
Inference

Compounds Studied
Cyclohexan Cyclohexene
e

Hexane

Heptane

Benzene

Toluene

CH3(CH2)4
CH3

CH3(CH2)5
CH3

C6H12

C6H10

C6H6

C6H5CH3

Liquid

Liquid

Liquid

Liquid

Liquid

Liquid

Clear

Clear

Clear

Clear

Clear

Clear

Colorless
Plastic
BalloonLike
Formation
of Oily
Layer
Immiscible
No soot,
15 s
Flammable
No change

Colorless

Colorless

Colorless

Colorless

Colorless

ChlorineLike

Alcohol-Like

Gas-Like

Gas-Like

Rugby-Like

Formation of
Clear, Oily
Layer
Immiscible
With soot,
3s
Flammable
Turbid, brown
solution

Formation of
Orange, Oily
Layer
Immiscible
With soot,
18 s
Flammable
Immediate
decolorization
, brown
solution

Formation
of Clear,
Oily Layer
Immiscible
With soot,
10 s
Flammable

Formation
of Clear,
Oily Layer
Immiscible
With soot,
5s
Flammable

No change

No change

Formation
of Clear,
Oily Layer
Immiscible
No soot,
6s
Flammable
No change

No change

No change

No change

Colorless

No change

Turbid

Not Actively

Not Actively

Not Actively

Actively

Not Actively

Not Actively

Unsaturate
d

Unsaturate
d

Unsaturated

Unsaturated

Unsaturated

Unsaturated

E. Nitration
Test

Colorless

Colorless

Colorless

With black
precipitate

With Yellow,
Oily Layer

With Yellow,
Oily Layer

Inference

Not
Aromatic

Not
Aromatic

Not Aromatic

Not Aromatic

Aromatic

Aromatic

F. Basic
Oxidation

No change

No change

No change

Black

No change

No change

Not
oxidized

Not oxidized

Not
oxidized
Table 1. Results Obtained

Inference

Not
Not oxidized
oxidized
rbr/chem226/226expts/226_expt03_
[Link]
Oxidized

References:
Books:
Bathan, G.I., Bayquen, A.V., Cruz, C.T.,
Crisostomo, A.B., de Guia, R.M.,
Farrow, F.L., . . . Torres, P.C. (2014).
Laboratory Manual in Organic
Chemistry. Quezon City: C & E
Publishing, Inc.
McMurry, J. (2016). Organic Chemistry.
Singapore: Cengage Learning Asia
Pte Ltd.
Articles:
No author (2014). Combustion. Retrieved
November
15,
2016,
from
[Link]
tesize/science/ocr_gateway/carbon_
chemistry/carbon_fuelsrev2.shtml
Lecture Notes:
Esmalla, M.S.A. (2009). Classification Tests
for
Hydrocarbons.
Retrieved
November
15,
2016,
from
[Link]
2/Post-Lab-Notes
San Luis, J. (2013). Hydrocarbons.
Retrieved
November 15, 2015, from
[Link]
s/hydrocarbons-27066904
No author (2003). Experiment #3 Hydrocarbons. Retrieved November
15,
2016,
from
[Link]

Portable Document Files (from Internet):

No author (n.d.). Reaction of Alkenes.
Retrieved November 15, 2016 from
[Link]
[Link]
Appendix
Figure 1
[Link]
ition_sulfuric_acid.gif
Figure 2
[Link]
cience/ocr_gateway/carbon_chemistry/carb
on_fuelsrev2.shtml
Figure 3
[Link]
Wj00yrmteMDsdoAAwJiylyHuGiBg9pzqYnX1bP_qBSsup1uaI
Dc3jM2V6lXfGX7g3tZlrKuSbed3GLpNr_Bw
CJiA6ocbofTV2ugGC59mQRPjlCvcf83l9FBAfo
Figure 4
[Link]
mons/thumb/3/33/AlkeneAndBr2Reaction.p
ng/[Link]
Figure 5

[Link]
nic/images/[Link]

Figure 6
[Link]
2015/03/benzoic_acid_synthesis.jpg