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 conducted was Baeyer’s Test and the Iodine Test,
composed purely of Carbon (C) and Hydrogen (H) which determined which among the samples are
atoms covalently bonded to each other. [1] Since actively unsaturated. Another test performed was
Hydrocarbons have varied structures, it is the Nitration test, which is a test for aromaticity.
important that a system of classification is in And lastly, the Basic Oxidation Test which is a test
place. for alkylated aromatics or arene. [5]
Hydrocarbons may be classified based on the The objective of the experiment was to
molecular framework. [2] It may be acyclic and characterize hydrocarbons and to distinguish each
may be further classified as alkanes, alkenes, one based on their intrinsic physical properties,
alkynes. This class of hydrocarbons form an open- chemical properties, structure, and behavior.
ended structure which may be branched or
unbranched. [3] On the other hand, cyclic EXPERIMENTAL
hydrocarbons are closed structure of carbons A. Samples used
which resembles a ring. In the experiment conducted, six (6) organic
Hydrocarbons may also be classified based on compounds were used, namely Hexane, Heptane,
active saturation. It may be saturated which Cyclohexane, Cyclohexene, Benzene, and
contains only carbon-carbon single bonds and that Toluene. Based on their structure, Hexane,
each carbon is bonded to the maximum number of Heptane, and Cyclohexane are the saturated
Hydrogen atom. Conversely, a hydrocarbon which hydrocarbons while the Cyclohexene, Benzene,
contains one or more carbon-carbon double and Toluene are the unsaturated hydrocarbons. [5]
bonds, triple bonds, or benzene rings is an The test compounds are shown in Table 1.
unsaturated hydrocarbon. [4]
The series of experiments conducted aims to A. Procedure
test for the presence of certain characteristic The experiment had a total of seven individual
reaction of each sample based on their properties, tests namely, Physical Characteristics, Solubility in
such as flammability, active unsaturation, conc. H2SO4, Ignition Test, Baeyer’s Test, iodine
aromaticity, and the substituent attached to Test, Nitration Test, and Test for Basic Oxidation.
aromatic organic compounds. The first test
conducted was the recording of the samples’ 1. Physical Characteristics
physical appearance, as well as their evaporation The physical appearance of each sample was
time. The second experiment was the Solubility in noted. Five (5) drops of each sample was placed
conc. H2SO4 which determined the miscibility of in a watch glass and to allow it to evaporate, the
the samples. The third experiment that was time it took for the sample to evaporate was
conducted looked into the flammability and the recorded.
presence of unsaturation of the samples through
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
Figure 2. Preparation of Samples and Reagent for
Iodine Test
Toluene C7H8
6. Nitration Test
Two (2) mL of conc. HNO3 was placed in an
Erlenmeyer flask and was placed on an
2. Solubility in conc. H2SO4
evaporating dish with water. 2 mL of conc. H 2SO4
Six (6) test tubes were prepared, 1mL of conc.
were gradually added into the flask and was cooled
H2SO4 were placed in each one. Then, 1 drop of
to room temperature, this served as the nitrating
each sample were added into the test tubes. Color
mixture. Five (5) drops of each sample was placed
and/or temperature change of the mixture were
on a test tube, then eight (8) drops of the nitrating
noted. For disposal, the solution in each test tube
mixture was added. Observation for the formation
were neutralized with 2 mL 10% NaOH and was
of a yellow oily layer was made and then the
placed in the waste bottle provided.
mixture was diluted with twenty (20) drops of
water. For waste disposal, the solution and the
3. Ignition Test nitrating mixture was placed in a large beaker for
Five (5) drops of each sample was placed in a the slow dilution of 20 mL of water. Small amounts
small evaporating dish, then a lighted match was of Na2CO3 was added until foaming stopped, the
applied to each one. The residue as well as the resulting solution was placed in the appropriate
color of the flame was recorded. 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
 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

Figure 4. Preparation of Samples and combustion reaction which produced CO2 and
Reagents for the Basic Oxidation H2O.[9]
Test
C7H16 + 11O2 → 7CO2 + 8H2O
RESULTS AND DISCUSSION
All of the organic compounds used namely Figure 6. Combustion Reaction of Heptane
Hexane, Heptane, Cyclohexane, Cyclohexene,
Benzene, and Toluene are clear, colorless liquids. On the Ignition Test, the Heptane underwent a
Among the samples used, the most volatile was combustion reaction producing CO2 and H2O. [10]
Hexane with only 79 seconds evaporation time,
and the least volatile among the samples is C6H12 + 9O2 → 6CO2 + 6H2O
toluene with a total of 698 seconds evaporation
time. The main principle involved here is the Figure 7. Combustion Reaction of Cyclohexane
intermolecular forces (IMF). Generally,
hydrocarbons are volatiles because of their weak On the Ignition Test, the Cyclohexane
IMF. The more carbon atoms the hydrocarbon underwent a combustion reaction which produced
have, the less volatile it will become because of CO2 and H2O. [11]
stronger IMF. Similarly, the more atom in a
molecule, the stronger the IMF making it less 2C6H10 + 17O2 → 12CO2 + 10H2O
volatile. [6]
Figure 8. Combustion Reaction of Cyclohexene
In the solubility Test using conc. H2SO4,
miscibility of the compounds tells if the sample is On the Ignition Test, the Cyclohexene
basic which can be protonated or neutral which underwent a combustion reaction which produced
cannot be protonated. Additionally, the dissolution CO2 and H2O. [12]
of compounds in H2SO4 may exhibit color change,
formation of precipitation, or production of heat, 2C6H6 + 15O2 → 12CO2 + 6H2O
or the combination of any of these. [5] Alkenes
react with cold concentrated sulfuric acid by Figure 9. Combustion Reaction Benzene
addition. Alkyl sulfonic acids form as products and
are soluble in H2SO4. Saturated hydrocarbons On the Ignition Test, the Benzene underwent a
are unreactive (additions are not possible); combustion reaction which produced CO2 and
alkynes react slowly and require a catalyst H2O.[13]
(HgSO 4 ); aromatic compounds also are
unreactive since addition reactions are difficult. C7H8 + 9O2 → 7CO2 + 4H2O
[7]

Figure 10. Combustion Reaction of Toluene

The Ignition Test was performed to indicate the
presence of unsaturation (high Carbon to On the Ignition Test, the Toluene underwent a
Hydrogen ratio). [5] All of the hydrocarbons combustion reaction which produced CO2 and
underwent combustion in the presence of oxygen. H2O.[14]
If the combustion is complete the products will be
In the Baeyer’s test the positive result is
CO2 and H2O, and heat is given off – the reaction
obtained if there is a decolorization and formation
is highly exothermic.[8] Generally, high carbon to
of a brown precipitate. Only cyclohexene gave a
hydrogen ratio equals high luminosity and the
positive result which means that it is actively
more the flame produces black smoke or soot. The
unsaturated and it contains double bond in its
degree of luminosity can be assessed by the
chemical structure.
presence of yellow flame and soot. Complete
 +

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

 answer/the-combustion-of-hexane-
c6h14 -is-represented-in-the-bala nced-
equation-2-c6h14-19-o-12-co2-14-
h2o-mmhexane-86-18-g-mole-o2-32-g
mole-co2-44-g-mole-h2o-18-g-mole-a-
if-45-g-of-hexane-i.html.

[10] Amin, S., Hanania, A., et al. (2017). Energy

education - Heptane. Retrieved from:
https://energyeducation.ca/encyclopedi
a/Heptane.
Figure 17. Result of Basic Oxidation Test
[11] Sharikendrick. (n.d.). Complete combustion
of Cyclohexane. Retrieved from : given-
complete-combustion-cyclohexane-c6h
12-9o2-gt-617907.

Figure 18. Basic Oxidation Test of Cyclohexene [12] Bhattacharyya, S. (2018). What is the
Combustion reaction of Cyclohexane.
Retrieved from: https://www.quora.
REFERENCES: com/What-is-the-combustion-reaction-
[1] Bettelheim, F., Brown, W., et al. (2016). of-cyclohexene.
Introduction to General, Organic, and
Biochemistry (11th ed.).Massachusetts, [13] Combustion of Benzene. (n.d.). Retrieved
USA: Cengage Learning. from: https://www.enotes.com/home
work-help/write-balanced-chemical-
[2] Bathan, G., Daya, M., et al. (2019) equation-combustion-c6h6-l-358511.
Laboratory Manual in Inorganic and
Organic Chemistry. [14] Combustion of Toluene. (n.d.). Retrieved
from: https://www.chegg.com/home
[3] Carey, F. (n.d.). Hydrocarbon. Retrieved work-help/questions-and-answers/1-
from: https://www.britannica.com/ combustion-toluene-toluene-undergoes-
science/hydrocarbon. standard-combustion-oxygen-form-
carbon-dioxide-wate-q4476254.
[4] American Chemical Society. (2015). Acyclic
and alicyclic Hydrocarbons. Retrieved [15] Sulphonation of Benzene and Nitration of
from: https://pubs.acs.org/doi/abs/ Nitrobenzene. (n.d.). Retrieved from:
10.1021 /ba-1974-0126.ch002. https://byjus.com/chemistry/benzene-
reactions/
[5] Caragay, C., Cariggal, R., et al. (n.d.).
Classification Tests For Hydrocarbons. [16] Oxidation of Organic Molecules by KMnO4.
(2019). Retrieved from: https://chem.
[6] Hydrocarbons: Intermolecular Forces and libretexts.org/Bookshelves/Organic_
Safety issues. (n.d.). Retrieved from: Chemistry/Supplemental_Modules_
https://study.com/academy/lesson/ (Organic_Chemistry)/Reactions/
hydrocarbons-intermolecular-forces Oxidation_and_Reduction_Reactions/
-safety-issues.html. Oxidation_of_Organic_Molecules_by_
KMnO4.
[7] Hydrocarbons. (n.d.). Retrieved from:
webhost.bridgew.edu › ihutchins ›
1.Hydrocarbons.docxHydrocarbons.

[8] Experiment #3 – Hydrocarbons. (n.d.).

Retrieved from: http://employees.
oneonta.edu/ knauerbr/chem226/
226expts /226_expt03_pro.pdf.

[9] The Combustion of Hexane. (n.d.). Retrieved

from: https://study.com/academy/