CHARACTERISTIC REACTIONS OF HYDROCARBONS

Kenneth L. Esmeralda, Krisius Ionnis De Guzman, Alexandra Janine Foronda, Kristeen Kyle
Geronimo, Danniella Grace Grecia, Tricy Fate Hondrada
Group 3 1F Medical Technology Inorganic and Organic Chemistry Laboratory

ABSTRACT
Hydrocarbons is a class of organic compounds composed purely of Carbon and Hydrogen atoms. The objective of the
experiment was to differentiate between hydrocarbons based on their intrinsic physical properties, chemical properties,
structure and behavior. The test compounds were subjected to different physical and chemical tests to characterize
each one based on flammability, active unsaturation and aromaticity. Physical state, color, odor and volatility were
noted through simple observation. Solubility of the test compounds were noted by introducing the samples into a test
tube with conc. H2SO4. Flammability of the samples were tested by igniting the sample into a small evaporating dish.
The test compounds was also subjected to Baeyer’s Test and Iodine Tests to test for active unsaturation; It was done
by introducing 2% KMnO4 into a test tube with the sample for the Baeyer’s Test and 0.5% I2 in CCl4 into a test tube
with the sample for the Iodine Test. Nitration test was done by adding the nitrating mixture made from HNO3 and of
H2SO4 into a test tube with the sample. For the basic oxidation test, 2% KMnO 4 and 10% NaOH was added into a test
tube containing the sample. All of the test compounds were liquid and colorless. Miscibility test showed that all of the
test compounds were immiscible and all are flammable. Baeyer’s test and Iodine test indicate that only cyclohexene
was actively unsaturated. Among all the test compounds, only Benzene and Toluene tested positive for nitration test
which means that they are aromatic. For the basic oxidation test, cyclohexene exhibited color change.

INNTRODUCTION the use of the Ignition Test. The fourth test

Hydrocarbons, is a class of organic compounds
composed purely of Carbon (C) and Hydrogen (H)
atoms covalently bonded to each other. [1] Since
Hydrocarbons have varied structures, it is
important that a system of classification is in
place.
Hydrocarbons may be classified based on the
molecular framework. [2] It may be acyclic and
may be further classified as alkanes, alkenes,
alkynes. This class of hydrocarbons form an open-
ended structure which may be branched or
unbranched. [3] On the other hand, cyclic
hydrocarbons are closed structure of carbons
which resembles a ring.
Hydrocarbons may also be classified based on
active saturation. It may be saturated which
contains only carbon-carbon single bonds and that
each carbon is bonded to the maximum number of
Hydrogen atom. Conversely, a hydrocarbon which
contains one or more carbon-carbon double
bonds, triple bonds, or benzene rings is an
unsaturated hydrocarbon. [4]
The series of experiments conducted aims to
test for the presence of certain characteristic
reaction of each sample based on their properties,
such as flammability, active unsaturation,
aromaticity, and the substituent attached to
aromatic organic compounds. The first test
conducted was the recording of the samples’
physical appearance, as well as their evaporation
time. The second experiment was the Solubility in
conc. H2SO4 which determined the miscibility of
the samples. The third experiment that was
conducted looked into the flammability and the
presence of unsaturation of the samples through
conducted was Baeyer’s Test and the Iodine Test,
which determined which among the samples are
actively unsaturated. Another test performed was
the Nitration test, which is a test for aromaticity.
And lastly, the Basic Oxidation Test which is a test
for alkylated aromatics or arene. [5]
The objective of the experiment was to
characterize hydrocarbons and to distinguish each
one based on their intrinsic physical properties,
chemical properties, structure, and behavior.
EXPERIMENTAL
A. Samples used
In the experiment conducted, six (6) organic
compounds were used, namely Hexane, Heptane,
Cyclohexane, Cyclohexene, Benzene, and
Toluene. Based on their structure, Hexane,
Heptane, and Cyclohexane are the saturated
hydrocarbons while the Cyclohexene, Benzene,
and Toluene are the unsaturated hydrocarbons. [5]
The test compounds are shown in Table 1.
A. Procedure
The experiment had a total of seven individual
tests namely, Physical Characteristics, Solubility in
conc. H2SO4, Ignition Test, Baeyer’s Test, iodine
Test, Nitration Test, and Test for Basic Oxidation.
1. Physical Characteristics
The physical appearance of each sample was
noted. Five (5) drops of each sample was placed
in a watch glass and to allow it to evaporate, the
time it took for the sample to evaporate was
recorded.
Table 1. Molecular and Structural Formula of the 5. Iodine Test
Samples Used Five (5) drops of each sample was placed in a
Molecular Structural test tube, then 10 drops of 0.5% I2 were added on
Sample
Formula Formula each sample. The mixture was then shaken
vigorously and any change in color as well as the
Hexane CH3(CH2)4CH3 time it took for the change to happen was
recorded. Samples that did not exhibit color
Heptane CH3(CH2)5CH3 change was exposed to sunlight.

Cyclohexane C6H12

Cyclohexene C6H10

Benzene C6H6
Toluene C7H8
2. Solubility in conc. H2SO4
Six (6) test tubes were prepared, 1mL of conc.
H2SO4 were placed in each one. Then, 1 drop of
each sample were added into the test tubes. Color
and/or temperature change of the mixture were
noted. For disposal, the solution in each test tube
were neutralized with 2 mL 10% NaOH and was
placed in the waste bottle provided.
3. Ignition Test
Five (5) drops of each sample was placed in a
small evaporating dish, then a lighted match was
applied to each one. The residue as well as the
color of the flame was recorded.
Figure 2. Preparation of Samples and Reagent for
Iodine Test
6. Nitration Test
Two (2) mL of conc. HNO3 was placed in an
Erlenmeyer flask and was placed on an
evaporating dish with water. 2 mL of conc. H 2SO4
were gradually added into the flask and was cooled
to room temperature, this served as the nitrating
mixture. Five (5) drops of each sample was placed
on a test tube, then eight (8) drops of the nitrating
mixture was added. Observation for the formation
of a yellow oily layer was made and then the
mixture was diluted with twenty (20) drops of
water. For waste disposal, the solution and the
nitrating mixture was placed in a large beaker for
the slow dilution of 20 mL of water. Small amounts
of Na2CO3 was added until foaming stopped, the
resulting solution was placed in the appropriate
waste bottle.

4. Baeyer’s Test
Five (5) drops of the samples was placed in a
test tube. For every sample, 2 drops of 2% KMnO4
was added, each one of the solutions were shaken
vigorously. The rate and extent, as well as the
time of color change were noted.

Figure 3. Preparation of Samples for the Nitration

Test

7. Test for Basic Oxidation

Five (5) drops of the sample was placed in a test
tube, followed by eight (8) drops of 2% KMnO4
(aq.) and three (3) drops of 10% NaOH (aq.). The
Figure 1. Preparation of Samples for Baeyer’s rate and extent of color change was recorded.
Test

Figure 4. Preparation of Samples and
Reagents for the Basic Oxidation
Test
RESULTS AND DISCUSSION
All of the organic compounds used namely
Hexane, Heptane, Cyclohexane, Cyclohexene,
Benzene, and Toluene are clear, colorless liquids.
Among the samples used, the most volatile was
Hexane with only 79 seconds evaporation time,
and the least volatile among the samples is
toluene with a total of 698 seconds evaporation
time. The main principle involved here is the
intermolecular forces (IMF). Generally,
hydrocarbons are volatiles because of their weak
IMF. The more carbon atoms the hydrocarbon
have, the less volatile it will become because of
stronger IMF. Similarly, the more atom in a
molecule, the stronger the IMF making it less
volatile. [6]
In the solubility Test using conc. H2SO4,
miscibility of the compounds tells if the sample is
basic which can be protonated or neutral which
cannot be protonated. Additionally, the dissolution
of compounds in H2SO4 may exhibit color change,
formation of precipitation, or production of heat,
or the combination of any of these. [5] Alkenes
react with cold concentrated sulfuric acid by
addition. Alkyl sulfonic acids form as products and
are soluble in H2SO4. Saturated hydrocarbons
are unreactive (additions are not possible);
alkynes react slowly and require a catalyst
(HgSO 4 ); aromatic compounds also are
unreactive since addition reactions are difficult.
[7]
The Ignition Test was performed to indicate the
presence of unsaturation (high Carbon to
Hydrogen ratio). [5] All of the hydrocarbons
underwent combustion in the presence of oxygen.
If the combustion is complete the products will be
CO2 and H2O, and heat is given off – the reaction
is highly exothermic.[8] Generally, high carbon to
hydrogen ratio equals high luminosity and the
more the flame produces black smoke or soot. The
degree of luminosity can be assessed by the
presence of yellow flame and soot. Complete
combustion is shown by a blue flame (non-
luminous); hence the carbon is completely
oxidized. Conversely, incomplete combustion is
indicated by a yellow flame (luminous);hence the
carbon is not completely oxidized. [5]
2C6H14 + 19O2 → 12CO2 + 14H2O
Figure 5. Combustion Reaction of Hexane
On the Ignition Test, the Hexane underwent a
combustion reaction which produced CO2 and
H2O.[9]
C7H16 + 11O2 → 7CO2 + 8H2O
Figure 6. Combustion Reaction of Heptane
On the Ignition Test, the Heptane underwent a
combustion reaction producing CO2 and H2O. [10]
C6H12 + 9O2 → 6CO2 + 6H2O
Figure 7. Combustion Reaction of Cyclohexane
On the Ignition Test, the Cyclohexane
underwent a combustion reaction which produced
CO2 and H2O. [11]
2C6H10 + 17O2 → 12CO2 + 10H2O
Figure 8. Combustion Reaction of Cyclohexene
On the Ignition Test, the Cyclohexene
underwent a combustion reaction which produced
CO2 and H2O. [12]
2C6H6 + 15O2 → 12CO2 + 6H2O
Figure 9. Combustion Reaction Benzene
On the Ignition Test, the Benzene underwent a
combustion reaction which produced CO2 and
H2O.[13]
C7H8 + 9O2 → 7CO2 + 4H2O
Figure 10. Combustion Reaction of Toluene
On the Ignition Test, the Toluene underwent a
combustion reaction which produced CO2 and
H2O.[14]
In the Baeyer’s test the positive result is
obtained if there is a decolorization and formation
of a brown precipitate. Only cyclohexene gave a
positive result which means that it is actively
unsaturated and it contains double bond in its
chemical structure.
 +

Cyclohexene Iodine (I2) trans-1,2-diiodocyclohexane

Figure 14. Iodine Test of Cyclohexene

Positive result for the Nitration Test is indicated

by the formation of yellow oily layer. Only Benzene
and Toluene showed positive result. In the
Figure 11. Result of Bayer’s Test experiment, Nitric acid accepts a proton from
sulphuric acid and then dissociates to form
nitronium ion. The nitronium ion acts as an
C6H10 + KMnO4 → 1,2-cyclohexanediol + MnO2 electrophile in the process which further reacts
(Purple) (colorless) (brown) with benzene to form an arenium ion. The arenium
ion then loses its proton to Lewis base forming
Figure 12. Reaction of Cyclohexene with KMnO4 nitrobenzene.[15]

In the reaction, Mn7+ is reduced to Mn4+ which

means that alkene is oxidized to a diol. Alkenes
react with KMnO4 because of their stability to give
a diol and MnO2. Aromatic compounds are stable,
hence they do opt react in this test. [5] Dilute or
alkaline solutions of KMnO4 oxidize unsaturated
compounds. Alkanes and aromatic compounds
are generally unreactive. [8]
Iodine Test confirms if the sample is actively
unsaturated. Hydrocarbons with multiple bonds
(unsaturated hydrocarbons except most Figure 14. Result of Nitration Test
cycloalkanes) react with Iodine. Alkenes and
alkynes undergo an addition reaction with Iodine.
The double bond of an alkene becomes a single
bond and one Iodine atom becomes bonded to
each of the carbons that had shared the double
bond. No other product is formed; the alkene and
Iodine simply add together. The triple bond of an Figure 15. Nitration of Benzene
alkyne also undergoes an addition becoming a
single bond.[5] Cyclohexene yields a positive result
because it only has one double bond making it
easy for the Iodine atoms to bond. Benzene and
toluene have double bonds but yield a negative
result because of their stability due to the concept
of Resonance. Iodine atoms or any other atoms Figure 16. Nitration of Toluene
cannot bond easily to compounds with perfect
stability. Hexane, heptane, and cyclohexane are The Basic Oxidation Test is a test for alkylated
all negative because they only have a single bond aromatics or arenes. A positive result in the test
(saturated) and thus showing no reaction. will produce a violet solution (MnO4). NaOH
provides a basic environment. The alkyl group of
the aromatic compound is oxidized to a carboxylic
acid, therefore involves a redox reaction. Mn7+ is
reduced to Mn6+/4+ depending on the extent of the
reaction.[5] All but Cyclohexene did not exhibit any
color change. [16]

Figure 13. Result of Iodine Test


Figure 17. Result of Basic Oxidation Test
Figure 18. Basic Oxidation Test of Cyclohexene
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