Classification Tests for Hydrocarbons

Authors: Goldie Ann Tejada, Allain Joseph S. Templo, Kristinlyn Trajano, Kevin Viray, Quennie Yu

Group 10, 2F-PH, Faculty of Pharmacy, University of Santo Tomas

ABSTRACT

The test compounds undergo different physical and chemical tests to differentiate their intrinsic physical properties and chemical
properties. Physical state, color, and odor were noted through simple observation. Miscibility of the test compounds were noted
through color change or a warming effect. Flammability was tested by igniting 3-5 drops of the sample in a small evaporating dish.
Baeyer’s test and Bromine test were used for tests for active unsaturation. Aromaticity of the compound was determined through
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 and warming the mixture through water bath. All of the test compounds are liquid and
colorless and observed to have a plastic like odor. Miscibility test shows that all of the organic compounds are immiscible and all are
flammable. Tests for active unsaturation indicate that hexane, heptane, cyclohexane, benzene and toluene are saturated while
cyclohexene is actively unsaturated. Hexane, heptane, benzene, and toluene are classified as aliphatic while cyclohexane, and
cyclohexene are aromatic. All are not oxidized except for cyclohexene.

Introduction Ignition test indicates the presence of unsaturation

Hydrocarbons are compounds that contain only
carbon and hydrogen. Hydrocarbons can be
aromatic or aliphatic depending on their structure.
Hydrocarbons that contain a delocalized ring of pi
bonds are called aromatic hydrocarbons and those
without a delocalized ring of pi bonds are called
aliphatic hydrocarbons. To be classified as
Aromatic, a compound must have an uninterrupted
cyclic cloud of pi electrons above and below the
plane of the molecule and there should be an odd
number of pairs of pi electrons in its pi cloud. To be
classified as Aliphatic, a compound must have
higher hydrogen-to-carbon ratios. Aliphatic
hydrocarbons that contain only sigma bonds are
called saturated hydrocarbons and those containing
both sigma and pi bonds are called unsaturated
hydrocarbon. Aliphatic hydrocarbons are divided
into 3 classes: alkanes are saturated hydrocarbons
that contain only carbon-carbon single bonds.
Alkenes are unsaturated hydrocarbons that contain
at least one carbon-carbon double bond. Alkynes
are unsaturated hydrocarbons that contain at least
one carbon-carbon triple bond.
Most hydrocarbons are colorless and odorless.
Solubility of organic compounds in H2SO4 indicates
whether the sample is a very weak base (can be
protonated) or a neutral compound (can’t be
protonated). The dissolution of compounds in
H2SO4 may also produce large amounts of heat
and/or a change in the color of the solution and
precipitation; this means that the reaction can be
either violent or slow.
or high carbon to hydrogen ratio. 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.
Bayer’s test is a test for double bonds or alkenes.
The reagent used for the test is 2% KMnO4.
Aromatic compounds show no reation in the test,
because of their stability. A positive result for
Bayer’s test shows decolorization of a purple
solution and formation of a brown precipitate
(MnO2). Bayer’s test involves a redox reaction were
in Mn7+ is reduced to Mn4+ and alkene is oxidized
to a diol. Alkenes react with potassium
permanganate (KMnO4) to give a diol and MnO2.
Bromine test, like Bayer’s test, is a test for double
bonds and aromatic compounds also show no
reaction in the test as they are known for their
stability. The reagents used are 0.5% Br2 in CCl4.
A Positive result shows decolorization of an orange
solution. Bromine test involves electrophilic
addition reaction were in Alkenes react with Br2 to
form a trans-dibromoalkane.
Test for Aromaticity is determined through
Nitration. The reagents used are HNO3, H2SO4. A
Positive result shows a yellow oily layer. The
reaction involves electrophilic substitution reaction
were in H2SO4 acts as a catalyst and facilitates the
formation of nitronium ion (electrophile) and one
hydrogen atom in the benzene ring is substituted by
the nitronium ion.
Oxidation was tested using 2% KMnO4 and 10%
NaOH. A Positive result shows a green solution and
a brown precipitate. The reaction involves redox
reaction and NaOH is used to provide a basic
environment. The alkyl group of the aromatic
compound is oxidized to a carboxylic acid while
Mn7+ is reduced to Mn6+ or Mn4+ depending on
the extent of the reaction.
Experimental
Physical state, color, and odor
The physical states of the sample were observed
at room temperature. Then the color and odor was
noted.
Solubility in Concentrated H2SO4
1 ml of concentrated H2SO4 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.
Ignition Test
3-5 drops of the sample were placed in a small
evaporating dish and was lighted by using a match.
Presence and color of the flame were noted.
Tests for Active Unsaturation
Baeyer’s Test
2 drops of 2% KMnO4 was added to 5 drops of
the sample in a dry test tube. The solution was
vigorously shaken and the rate and extent at which
the reagent is decolorized was observed. The
formation of a brown suspension was noted and
compared to water as a negative control. The result
must be noted, once the reagent decolorized within
a minute.
Bromine Test
10 drops of 0.5% Br2 in CCl4 reagent were added
5 drops of the sample. The mixture was vigorously
shaken and the rate and extent by which the reagent
is decolorized was observed. It was compared to
water as a negative control. If the reagent failed to
decolorize within a minute, expose the reaction
mixture to sunlight and note down the results.
Test for Aromaticity
2 mL of conc. HNO3 was placed in an Erlenmeyer
flask and was immersed in an evaporating dish
containing water. 2mL of conc. H2SO4 was
gradually added to the flask and was allowed to
cool at room temperature. The resulting mixture
will serve as nitrating mixture.
8 drops of the nitrating mixture was added to 5
drops of the sample in a dry test tube and was
vigorously shaken to ensure complete mixing. The
formation of a yellow layer or droplet was noted
and 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.
Basic Oxidation
8 drops of 2% KMnO4 and 3 drops of 10% NaOH
solution were added to 4 drops of the sample in a
test tube. Each test tube was warmed in a water bath
for 2 minutes and formation of a brown precipitate
was noted.
Results and Discussions
It was observed that all 6 test compounds are
immiscible in concentrated H2SO4; since alkanes,
alkyl halides, aryl halides, and most hydrocarbons
are insoluble in concentrated H2SO4. All 6 test
compounds are flammable. All except hexane and
heptane produced soot due to incomplete
combustion which causes the formation of an
unburned carbon. Only cyclohexene behaved as an
actively unsaturated hydrocarbon. Hexane, Heptane,
Benzene, and Toluene were considered as aromatic
while the cyclohexane and cyclohexene are
aliphatic. Only cyclohexene was oxidized.
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