CLASSIFICATION TESTS FOR HYDROCARBONS

AUTHORS: Dizon, S., *Donato, A.K., Dy, A., Enriquez, K.B., Fauni, M.B.

ABSTRACT:

The organic compounds hexane, heptane, cyclohexane, cyclohexene,

benzene, and toluene were subjected to different physical and chemical tests to
differentiate their intrinsic physical properties and chemical properties in terms of
structure and behavior. The physical state, color, and odor were noted by simple
physical observation. Miscibility was tested by introducing a drop of the sample to 1 ml
concentrated H2SO4. Flammability was tested by placing 3-5 drops of the sample to an
evaporating dish and lighting it with a match. Active unsaturation was tested using the
Baeyer’s and Bromine test and aromaticity was determined by subjecting the organic
compounds to Nitration. Oxidation was tested by introducing 8 drops of 2% KMnO4
solution and 3 drops of 10% NaOH solution to 4 drops of the sample organic compound
in a test tube. All organic compounds showed immiscibility in concentrated H2SO4 and
flammability in the ignition test. All but cyclohexane were not actively unsaturated. All
turned out to be aromatic compounds except cyclohexane and cyclohexene. All are not
oxidized except cyclohexene.

I.)INTRODUCTION Unsaturated hydrocarbons have similar

Hydrocarbons are compounds
that contain only carbon and hydrogen
atoms. Hydrocarbons may be divided into
two large classes namely: Saturated
hydrocarbons and Unsaturated
hydrocarbons. Saturated hydrocarbons are
the simplest type of organic compounds.
They are hydrocarbons in which all carbon-
carbon bonds are single bonds. An example
of a saturated hydrocarbon is an alkane.
Unsaturated hydrocarbons are
hydrocarbons that contain one or more
carbon-carbon multiple bonds like double
bonds, triple bonds, or both. Saturated and
physical properties, but their chemical
properties are different. Unsaturated
hydrocarbons are chemically more reactive
than saturated ones. This is because of the
presence of carbon-carbon multiple bonds
in such compounds and these multiple
bonds serve as locations were chemical
reactions can occur.
Fig. 1 (Unsaturated hydrocarbon)
 Cyclohexane is a cycloalkane
with the molecular formula C6H12, molar
mass of 84.160 g/mol, and boiling point of
80.74°C. 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. 2 (Saturated hydrocarbon)

Fig. 5 (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°C. It is not very stable upon long
term storage and exposure to light and air
should be distilled before use to eliminate
Fig. 3 (Summary of classification of organic peroxides. It has a very sharp smell
compounds) resembling an oil refinery.

Hexane is an alkane
hydrocarbon with a chemical formula of
C6H14, molar mass of 86.18 g/mol, and a
boiling point of 69°C. 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 Fig. 6 (Structure of cyclohexene)
leather products.
Benzene is an organic
chemical compound with a molecular
formula of C6H6, molar mass of 78.11
g/mol, and a boiling point of 80.1°C. It is
a colorless, highly flammable liquid with a
sweet smell. It is a known carcinogen,
Fig. 4 (Structure of hexane) 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.
Fig. 7 (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 110.6°C. Toluene reacts as
a normal aromatic hydrocarbon towards
electrophilic aromatic substitution. It is a
water-insoluble liquid with a smell of paint
thinners, and it is widely used as an
industrial feedstock and solvent.
Fig. 8 (Structure of Toluene)
Miscibility is the property of
liquids to to mix in all proportions,
therefore forming a homogenous solution.
By contrast, substances are considered
immiscible if in any proportion, they do not
form a solution. In organic compounds,
The miscibility is determined by the weight
percentage of the hydrocarbon chain. The
solvent used in the experiment is
concentrated H2SO4. If a compound is
unsaturated, it is said to be easily
sulfonated, or possesses a functional group
containing oxygen, it will dissolve in
sulfuric acid. Alkanes, cycloalkanes, and
their halogen derivatives are insoluble in
sulfuric acid. Simple aromatic
hydrocarbons and their halogen derivatives
do not undergo sulfonation and are also
insoluble in sulfuric acid. Nevertheless, the
presence of two or more alkyl groups on
the aromatic ring permits the compound to
be sulfonated easily. Many secondary and
tertiary alcohols are dehydrated readily by
concentrated sulfuric acid, which results to
the formation of olefins which then
undergo polymerization. The polymers
formed are insoluble in concentrated
sulfuric acid and forms a distinct layer on
top of the acid.
Flammability the measure of
the extent to which a material or a
substance will support combustion. The
degree of difficulty required to cause the
combustion of a substance is subject to
quantification through fire testing or
ignition test. Vapor pressure is an
important parameter in determining the
ease of ignition of a substance or material.
The higher the vapor pressure, the more
flammable vapor is evolved from a free
liquid surface at a given temperature.
Many compounds are determined by the
characteristics of their flame when they
burn. Aromatic hydrocarbons burn with a
yellow, sooty flame due to their high
carbon content. Aliphatic hydrocarbons
burn with flames that are yellow, but less
sooty.
 Baeyer’s test is a test for the In this experiment, the group
presence of unsaturation (double bonds). A should be able to attain the following
similar test can be done using bromine. objectives: (1) differentiate hydrocarbons
Baeyer’s test uses a solution called the in terms of intrinsic physical properties,
Baeyer’s reagent, which is a solution of and (2) differentiate hydrocarbons in terms
alkaline potassium permanganate. Reaction of chemical properties by noting their
with double or triple bonds in an organic structure and behavior towards different
material causes the color to fade from tests.
purplish-pink to brown. Easily oxidized
compounds like aldehydes, formic acid and
its esters, alcohols with trace of impurities, II.) EXPERIMENTAL
phenols, and thioethers give positive
results. Quantitatively, the iodine value is A.) Physical state, color, and odor
used to determine the presence of
unsaturation. The physical states of the
sample compounds HEXANE, HEPTANE,
CYCLOHEXANE, CYCLOHEXENE, and
BENZENE were observed at room
temperature. The color and odor was
noted.

Fig. 9 (Baeyer’s test in an alkene)

Aromaticity is the special

stability of planar, cyclic, fully conjugated
molecules with 4n + 2∏ electrons. Such
molecules have orbital systems with all
bonding molecular orbitals completely filled
with all antibonding and nonbonding
Fig. 10 (Schematic diagram 1)
orbitals empty. The criterion for a
compound to be aromatic is expressed by
the Huckel’s rule. B.) Solubility in concentrated H2SO4

The oxidation was tested using 1 ml of concentrated H2SO4

potassium permanganate. Potassium
permanganate is an inorganic compound
and a very strong oxidizing agent. It is
used in the determination of the total
oxidizable organic material in an aquaeous
sample. The value determined is known as
the permanganate value.
was added to each 6 test tubes. By using
dry and calibrated droppers, a drop of each
sample was added to the test tubes. Any
color change or warming effects were
noted.
 Reagent was considered immediate if it
occurred within a minute. The results were
noted down.

Fig. 11 (Schematic diagram 2)

C.) Ignition test

Fig. 13 (Schematic diagram 4)
3-5 drops of the liquid sample
(pinch amount of solid) were placed in an
evaporating dish and was lighted using a (2) Bromine test
match. Any flame produced was noted.
10 drops of 0.5% Br2 in CCl4
reagent were added to 5 drops of the
sample in a dry test tube. The test tube
was shaken vigorously and the rate and
extent of decolorization was observed. It
was compared with water as a negative
control. If the reagent failed to decolorize
within a minute, the reaction mixture was
exposed to sunlight.

Fig. 12 (Schematic diagram 3)

D.) Active unsaturation

(1) Baeyer’s test

2 drops of 2% KMnO4 were

added to 5 drops of the sample in a dry
test tube. The test tube was shaken Fig. 14 (Schematic diagram 5)
vigorously and the rate and extent at which
the reagent is decolorized was observed.
The formation of a brown suspension was
noted. It was compared with water as a
negative control. The decolorization of the
E.) Aromaticity: Nitration F.) Basic oxidation

2 ml concentrated HNO3 was 8 drops of 2% KMnO4 solution

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 (nitrating mixture) was cooled in
room temperature.
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.

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 (50°C) for 10 minutes. It was diluted
with 20 drops of water and the results
were noted down.

Fig. 16 (Schematic diagram 7)

Fig. 15 (Schematic diagram 6)

 After subjecting all 6 organic Stoker, S. Organic and Biological
samples to different physical and chemical Chemistry. 1998. Houghton Mifflin
tests, it was observed that all 6 organic Company. p. 5
samples were flammable and immiscible in
concentrated H2SO4. All except hexane and Stoker, S. Organic and Biological
heptane produced soot when ignited. Only Chemistry. 1998. Houghton Mifflin
cyclohexene behaved as an actively Company. p. 35-36
unsaturated hydrocarbon. All were
aromatic compounds except cyclohexane
and cyclohexene. The only compound
oxidized was cyclohexene.

IV.) SOURCES

Books:

Hornback, J.M. 1998. Organic Chemistry.

Brooks/ Cole Publishing Company, Pacific
grove. p.p 816-817

Maitland, J.J. 1997. Organic Chemistry.

w.w Norton and Company, USA. pp. 616

Shriner, Hermann, Morill, et. Al. 2004. The

Systematic Identification of Organic
Compounds. John Wiley and Sons Inc.
USA. p. 24

Shriner, Hermann, Morill, et. Al. 2004. The

Systematic Identification of Organic
Compounds. John Wiley and Sons Inc.
USA. p. 128

Shriner, Hermann, Morill, et. Al. 2004. The

Systematic Identification of Organic
Compounds. John Wiley and Sons Inc.
USA. p. 130