TESTS FOR HYDROCARBONS

Elaizha A. Carias, Alodia Eunicia O. Castillo, Aureo Paul D. Chiong, Alison A. Claveria, Jehhan
Decampong, and Regina Marie DG. De Guzman
Group 2 2G Pharmacy Organic Chemistry Laboratory
ABSTRACT
Hydrocarbons are organic compounds containing carbon and hydrogen atoms that are covalently bonded to each
other. In the experiment, they were classified by observing their solubility, flammability, active unsaturation,
aromaticity, and oxidation to their suitable tests. Hexane, heptane, cyclohexane, cyclohexene, benzene, and toluene
were subjected to different physical and chemical tests to differentiate their intrinsic physical and chemical properties
in terms of structure and behavior. The physical properties of the compounds were observed to identify their physical
state, color and odor. The compounds were all clear, colorless liquid, and they only vary in odor. Concentrated sulfuric
acid was the reagent used to test the miscibility. Ignition test was used for its flammability. All of the compounds were
flammable having luminous flames. Also, only the cyclic compounds produced soot. The active unsaturation was
tested too by using Baeyers and Bromine test. All the compounds reacted with 2% KMnO 4 solution in Baeyers Test.
Decolorization from purple to brown was only seen in cyclohexane, and cyclohexene. For the Bromine test, the
compounds were studied through their reaction with 0.5% Br 2 in CCl4 reagent. Immediate decolorization occurred in
all compounds except in toluene. After that, aromaticity of the compounds were tested. For this to be done, a nitrating
mixture composed of concentrated HNO 3 and concentrated H2SO4 was combined to the hydrocarbons. Aromatic
compounds were found out to be cyclohexene, benzene, and toluene, in which they all produced a yellow oily layer.

INTRODUCTION
Hydrocarbons are the simplest organic
compounds because it contains only carbon and
hydrogen. The carbon skeleton may be acyclic,
which is an open-chained, or cyclic, a closechained. Hydrocarbons, or molecules which
contain hydrogen atoms and carbon atoms that
are bonded to each other and may or may not
contain other atoms, are classified into two
distinct categories: saturated and unsaturated.
[1]

Figure 2. Saturated Hydrocarbon

Unsaturated hydrocarbons are compounds
that consist only of the elements carbon (C) and
hydrogen (H) and contain at least one carboncarbon double or triple bond. [3]

Figure 3. Unsaturated Hydrocarbon

Figure 1. Classification of Hydrocarbons

Saturated hydrocarbons are hydrocarbons
that contain only single bonds between
carbon atoms. They are the simplest class of
hydrocarbons. They are called saturated because
each carbon atom is bonded to as many
hydrogen atoms as possible. [2]

Numerous tests were performed to be

able to classify the physical and chemical
properties of the sample compounds: hexane,
heptane, cyclohexane, cyclohexene, benzene,
and toluene.
Miscibility is the property of substances to
mix in all proportions, forming a homogeneous
solution. It is most often applied to liquids, but
applies also to solids and gases. Substances are
said to be immiscible if a significant proportion

does not form a solution. Otherwise,

substances are considered miscible. [4]

the

The rule used in determining hydrocarbon

solubility is, like dissolves like. This just means
that polar compounds (water, alcohols, and
carboxylic acids) dissolve other polar compounds
and nonpolar compounds dissolve other nonpolar
compounds, but tend not to dissolve polar
compounds. It is miscible if the solutions have no
layers; and it is immiscible if the solutions have
layers.
Flammability test checks a number of
properties. Almost all organic compounds are
readily flammable.
Flammability is when the
compounds react exothermically with oxygen.
Because of the high heat of reaction, it means a
fire will result from the reaction. Most alcohols
and alkanes are prime examples. Their high
flammability is the result of their ease of reaction
with oxygen, and the large amount of heat given
out when they react. This heat results from the
formation the bonds in CO2 and H2O, which are
very stable and have less energy than the bonds
of the initial reactants. The excess energy is lost
as heat.
Yellow flames are luminous. Although they
can get at some oxygen, they can't get as much
as they need to turn all of the carbon that's being
burnt up into carbon dioxide. This is why this kind
of flame produces soot. Since it can't release all
of the carbon as CO2, some of it gets released as
the black stuff in smoke, which is the soot.

non-luminous. This just means that the nonluminous flames have a lot more energy than
luminous ones, and their flames are actually
hotter. This is why the luminous ones look yellow
and the non-luminous ones look blue. [5]
For the test in active unsaturation, two
different tests were done.
In Baeyers test, the presence of carboncarbon double bonded compounds, called alkenes
or carbon-carbon triple bonded compounds,
called alkyne bonds was determined. It uses
dilute Potassium Permanganate to oxidize the
carbon-carbon double or triple bond. It's called
oxidation because the double bond is replaced by
a hydroxyl group. The carbon's charge goes from
being +1 to +2, so it loses an electron (and is
thus oxidized).

Figure 5. Positive and negative result in Baeyers

Test
An alkene is replaced with a diol. There is
an evidence for the reaction because the purple
potassium permanganate goes colorless. Alkynes
work the same way, but a 4 hydroxy quattrol is
produced. The reaction is important because it
doesn't work on alkanes (compounds with
carbon-carbon
single
bonds)
or
aromatic
compounds. [6]

A bromine solution is also used to test

for unsaturation. This test is used to
determine if there is an alkene compound,
because if there is, the solution will be
colorless. Bromine does not react with an alkane
Figure 4. Luminous Flame
On the other hand, blue flames are nonluminous. These flames have access to as much
oxygen as they could possibly use, so they can
burn very efficiently. All of the carbon that gets
used can be turned into CO2, so there will be no
soot.
Luminous flames do not produce much
energy because they dont burn as efficient as

because it contains only single bonds which

cannot add the bromine. When an alkene is
reacted with bromine, the red-brown color of the
bromine is immediately lost due to the reaction of
the bromine. [7]

Figure 6. Results in Bromine Test

Aromaticity is a property associated with

the extra stability of certain types of p systems.
Fundamentally, it arises from having the
maximum
number
of
electrons
in
the p bonding molecular orbitals. As we will see,
it is not restricted to benzene, substituted
benzenes,
6-membered
rings
or
just
hydrocarbons. The property of aromaticity is
generally about a significant extra stability
associated
with
a
resonance
delocalized
structure. This extra stability moderates the
reactivity of these systems compared to alkenes
and means aromatics can be considered as their
own functional group. The presence of aromatic
systems can also influence the reactivity of
functional groups directly attached to the
aromatic system particularly in the benzylic
position. Therefore it is important that you are
able to recognize the aromatic systems.

The basic oxidation was tested using

potassium permanganate, an inorganic
compound and a very strong oxidizing agent.
It is used in the determination of the total
oxidizable organic material in an aqueous
sample. The value determined is known as
the permanganate value.
The objectives of this experiment were to
differentiate hydrocarbons in terms of intrinsic
physical properties, and chemical properties
based on structure and behavior. This also aims
to analyze a hydrocarbon and determine if it is
saturated, actively unsaturated, aromatic or an
arene.

Heptane is the name for the straightchained saturated hydrocarbon with seven
carbons and 16 hydrogens. The seven carbon
atoms are connected in one long chain with no
branches. It is said to be fully saturated, because
it contains no double bonds between carbons.
Hydrogens are attached such that each carbon
makes four bonds to other atoms. At room
temperature, heptane is a colorless liquid with a
gasoline-like odor. It readily gives off fumes, and
both the liquid and the fumes are highly
flammable. [9]

Figure 8. Structure of Heptane

Cycloalkane is a hydrocarbon with a
chemical formula of C6H12, which is a ring-like
structure. It has to have at least three alkane
compounds present to form a ring or a cycle
structure. It is a colorless, flammable liquid with
a petroleum-like odor. It is used in some foods,
hair care products, laundry detergents, nylon,
and paint removers. [10]

EXPERIMENTAL
A. Compounds Tested (or Samples used)
Hexane is an alkane hydrocarbon having a
chemical formula of C6H14, and a molar mass of
86.18 g/mol. It is a colorless liquid at room
temperature, odorless when pure, and with a
boiling point of 69C. Isomers of hexane are
typically non-reactive, and are often used as
solvents in organic reactions because they are
very non-polar. They are common constituents of
gasoline and leather products. [8]

Figure 7. Structure of Hexane

Figure 9. Structure of Cyclohexane

Cyclohexene is
a hydrocarbon with
a
chemical
formula
of
C6H10.
It is
a
colorless liquid with a gas-like odor, and is
insoluble in water as well as less dense
than water. This
cycloalkane
is
also
an
intermediate in various industrial processes. It is
not very stable upon long term storage with
exposure
to
light
and
air
because
it
forms peroxides. This may cause having a
narcotic effect if a high concentration has been
inhaled. [11]

Figure 12. Structure of Toluene

B. Procedure

Figure 10. Structure of Cyclohexene

Benzenes chemical formula is C6H6, so it
has six carbon (C) atoms and six hydrogen (H)
atoms. Its chemical structure can be described as
a hexagon ring with alternating double bonds, as
shown in figure 8. It is a liquid that is colorless
and flammable, with a sweet and little alcohollike odor. It a useful chemical substance but also
a toxic one, and continuous exposure to it can
have cancerous effects. This is because benzene
is a carcinogen, which means that it can
potentially cause cancer. [12]

Figure 11. Structure of Benzene

Toluene is also called as methylbenzene,
because a methyl is attached to benzene forming
a chemical formula of C7H8. It is considered
an aromatic compound because a benzene ring is
present in its chemical structure. [13] Toluene is
a clear, colorless liquid that has a little alcohollike odor, and is insoluble in water. It can be
dangerous when its fumes are inhaled, causing
neurological damage and intoxication.

1. Physical State, Color, and Odor

First, the physical state and appearance of
the sample at room temperature was observed,
and with a wafting motion of the hand over the
mouth of the test tube, the odor was
investigated.
2. Solubility in Concentrated H2SO4
Every separate test tube that has 1 mL of
concentrated H2SO4 has been added a drop of
each of the sample compounds by using a dry
and calibrated droppers. After that, change in
color and/or warming effect was noted.
3. Ignition Test
Flammability of the compounds was tested by
placing one by one 5 drops of each liquid sample
in a small evaporating dish and lighted with a
match.
4. Tests for Active Unsaturation
Two different tests were conducted to test the
organic compounds active unsaturation. In
Baeyers test, 5 drops of the sample was placed
in a dry test tube, and 2 drops of 2% KMnO 4 was
added to each. The formation of brown
suspension was observed and noted, and if the
reagent decolorized in 1 minute, then it is
immediate. Whereas in Bromine test, 5 drops of
the sample was added to 10 drops of 0.5 % Br2
in CCl4 reagent. The rate and extent of the
change in color was observed.
5. Test for Aromaticity: Nitration
2 ml concentrated HNO3 was placed in an
Erlenmeyer flask. The flask was immersed in an
evaporating dish containing water and 2 ml of
concentrated H2SO4 was added gradually. The
resulting
mixture
was
cooled
to
room
temperature. Then 8 drops of the nitrating
mixture was added to 5 drops of the sample in a
dry test tube. The test tube was shaken to
ensure complete mixing. The formation of a
yellow oily layer or droplet was noted, and then it
was diluted with 20 drops of water. If there was
no apparent reaction observed within a minute,
the test tube was placed in a water bath (50C)
for 10 minutes. It was diluted with 20 drops of
water and the results were noted down.
6. Basic Oxidation
1 drop of 2% KMnO4 solution, 7 drops of distilled
water, and 3 drops of 10% NaOH solution were
added to 4 drops of the sample in a test tube.
Each test tube was subjected to a water bath for
2 minutes. Any color change and formation of
brown precipitate was observed and noted down.

RESULTS AND DISCUSSION

Hexane

COMPOUNDS TESTED
Heptane

Cyclohexane

Condensed Structural
Formula
A. Physical state at RT
Appearance
Color
Odor
B. Solubility in conc. H2SO4
Inference
C. Ignition test
Inference
D. Baeyers test
Bromine test
Inference
E.

Test for aromaticity nitration

Inference
F.

Basic Oxidation
Inference

liquid

liquid

Liquid

All clear
colorless
odorless
immiscible
insoluble
luminous
flammable
purple

All clear
colorless
Alcohol-like odor
immiscible
insoluble
Luminous
flammable
purple

All clear
Colorless
Gas-like odor
Immiscible
Insoluble
6 seconds, luminous
Flammable, with soot
Brown

Immediate decolorization

Immediate decolorization

Immediate decolorization

No changes
Blue green

No changes
No changes

No changes
Blue green

Cyclohexene

COMPOUNDS TESTED
Benzene

Toluene

Condensed Structural
Formula
A. Physical state at RT
Appearance
Color
Odor
B. Solubility in conc. H2SO4
Inference
C. Ignition test
Inference
D. Baeyers test
Bromine test
Inference
E.

Test for aromaticity nitration

Inference
F.

Basic Oxidation
Inference

liquid

liquid

Liquid

All clear
colorless
Gas-like odor
immiscible
insoluble
30 seconds, luminous
Flammable, with soot
brown

All clear
colorless
Little alcohol-like odor
immiscible
insoluble
14 seconds, luminous
flammable, with soot
purple

All clear
Colorless
Little alcohol-like odor
Immiscible
Insoluble
13 seconds, luminous
Flammable, with soot
Brown

Immediate decolorization

Immediate decolorization

Immediate decolorization

No changes
Blue green

No changes
No changes

No changes
Blue green

After subjecting all 6 organic samples to different

physical and chemical tests, it was observed that
all organic samples were clear, colorless liquid.
Each compound has their own characteristic odor
that makes them distinguishable from the others.
The miscibility of the compounds in concentrated
H2SO4 indicates if the sample is a very weak
base or a neutral compound. The dissolution of
compounds in conc. H2SO4 may also produce
large amounts of heat and/or a change in the

color of the solution,

combination of these.

precipitation

or

any

Ignition test was done to indicate the presence of

high carbon to hydrogen ratio.

In general,
Carbon to hydrogen ratio, luminosity, soot.

The degree of luminosity can be assessed by the

presence of yellow flame and soot. Aromatic
compounds burn with sooty flame due to the
incomplete
combustion
which
causes
the
formation of an unburned carbon.
In terms of degree of luminosity,
aromatic compound unsaturated hydrocarbon,
unsaturated hydrocarbon saturated hydrocarbon
If the flame is blue or non-luminous, then it
results to a complete combustion, and the carbon
is completely oxidized.
On the other hand, incomplete combustion is
indicated by a yellow flame (luminous), and the
carbon is not completely oxidized.

Complete combustion:
C xH y + O 2

CO2 + H2O

H2O

http://www.ck12.org/book/CK-12-PhysicalScience-Concepts-For-MiddleSchool/section/3.33/ [2]
http://study.com/academy/lesson/unsaturatedhydrocarbon-definition-examples.html [3]

Incomplete combustion:
CxHy + O2

http://www.softschools.com/difference/saturated
_vs_unsaturated_hydrocarbons/156/ [1]

CO2 + CO + C (soot) +

https://en.wikipedia.org/wiki/Miscibility [4]
https://van.physics.illinois.edu/qa/listing.php?
id=1555 [5]
https://van.physics.illinois.edu/qa/listing.php?
id=505 [6]
http://www.paaet.edu.kw/mysite/LinkClick.aspx?
fileticket=2kjjKCWEjuc
%3D&tabid=2199&mid=3424&language=en-US
[7]
https://en.wikipedia.org/wiki/Hexane [8]
http://study.com/academy/lesson/heptanestructure-uses-formula.html [9]
http://study.com/academy/lesson/cycloalkanesdefinition-examples.html [10]
https://en.wikipedia.org/wiki/Cyclohexene [11]
http://study.com/academy/lesson/what-isbenzene-uses-structure-formula.html [12]
http://study.com/academy/lesson/what-istoluene-structure-uses-formula.html [13]
http://chemwiki.ucdavis.edu/Organic_Chemistry/
Hydrocarbons/Arenes/Properties_of_Arenes/Arom
aticity