CHARACTERISTIC REACTIONS OF HYDROCARBONS

Nasayao, P.I.B., Nogoy, J.M., Olaño, J.A.F.,

Olfato, M.A.M., Pamittan, J.M.L., Paraguison, C.D.
Group 5 1H Medical Technology Inorganic and Organic Chemistry Laboratory

ABSTRACT
Hydrocarbons are the simplest organic compounds consisting of carbons and hydrogens. The purpose of the
experiment was to understand and differentiate the characteristics of hydrocarbons. The compounds used were
cyclohexene, hexane, benzene and toluene. The organic compounds were tested qualitatively. The first test was
to analyze the physical state, color and odor of each organic compound. followed by numerous tests that
evaluated whether each sample was soluble with concentrated H2SO4, actively unsaturated by reacting with
basic oxidation test and Baeyer’s test, test for aromacity by utilizing nitration test, and flammable or
inflammable with the use of the ignition test. The test compounds were observed to be liquid at room
temperature and appeared clear and colorless. The positive results obtained were that cyclohexene is actively
unsaturated on both the Baeyer’s test and basic oxidation test. Cyclohexene also exhibited miscibility with conc.
H2SO4. Benzene and toluene developed an oily layer on the nitration test and considered aromatic. All
hydrocarbons are flammable and produced a yellow flame. Benzene produce the most amount of soot whereas
hexane exhibited the least amount of soot. These results may be attributed to the ratio between the carbon and
hydrogen.

molecular structure. A hydrocarbon can be

INTRODUCTION acyclic/open-chained or cyclic/closed-
chained [3]. Cyclic compounds can be
Hydrocarbons are the simplest organic further categorized as alicyclic or aromatic
compounds containing carbons and hydrocarbons. Alicyclic compounds hold a
hydrogens [1]. They’re covalently bonded ring of 3 or more carbons that resemble
which means that they share their electrons. aliphatic hydrocarbons while aromatic
Carbon has an electronegativity of 2.5 while compounds follow the alternating double
Hydrogen has an electronegativity of 2.2. bonds in conjugation and the Hückel's rule.
Their Pauling electronegativity difference is Secondly, they can be grouped in terms of
0.3 and it can be inferred that the bond the number of covalent bonds between its
between these elements are nonpolar carbon atoms. The first group are saturated
covalent bond. Hydrocarbons in this nature compounds which only consists of carbon-
means that the bonding electrons are shared carbon single bonds and all bonds of each
almost uniformly by neighboring atoms and carbon atom are saturated by hydrogen
this is the why there are no partial charges atoms. The second group are unsaturated
found within these molecules [2]. compounds which include one or more
multiple C-C bonds. In unsaturated
These hydrocarbons are classified compounds, pi electrons are involved which
according to 3 distinct characteristics. First, are called pi bonds and the multiple bond
they can be classified according to their can be either double or triple bond. Lastly,

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they can be organized either actively B. Procedure
unsaturated compounds or inactively
unsaturated compounds. Actively 1. Physical State, Color and Odor
unsaturated compounds have pi-bonds that
are easily broken whereas inactively
unsaturated compounds are stable and
possess unreactive pi-bonds due to
resonance [4].

The objective of the experiment is to

fully understand and differentiate the
properties of hydrocarbons. Hydrocarbons
have a lot of characteristics and the goal of
these procedures are to compare and contrast
the intrinsic physical properties such as
physical state and appearance, and the FIGURE 1. Observing the Physical State and
chemical properties such as flammability, Color of Hexane.
active unsaturation and aromaticity.
The physical state and appearance of
METHODOLOGY the organic compounds in room temperature
were observed. The color of the compounds
A. Compounds, Instruments, and was noted and with a drifting motion, the
Equipment Used. odor was described.

The organic compounds used that were 2. Solubility in conc. H2SO4

observed are hexane, cyclohexene, benzene
and toluene. Reagents that were used are
conc. H2SO4, 2% KMnO4 (aq.), 0.5% Br2 in
CCl4, conc. HNO3, and 10% NaOH.

Instruments that were used are test

tubes, test tube rack, test tube holder,
evaporating dishes, 250-mL Erlenmeyer
flask, droppers, beaker and litmus paper.
Equipment used in the experiment is a fume
hood.
FIGURE 2. Adding Drops of Hexane in a Test
Tube containing 1 mL of conc. H2SO4.

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 Into a test tube containing 1 mL of
conc. H2SO4, 1 drop of the organic
compound was added cautiously. The
organic compound was determined whether
it was miscible or immiscible. Any
darkening, color change or warming effect
was noted and the clean up involved
carefully neutralizing the solution with 10%
NaOH and the solution was placed in an
aqueous solution container provided.

3. Ignition Test FIGURE 4. Adding 2 Drops of 2% KMnO4

solution on an organic compound.

In a dry test tube, 5 drops of the organic

compound were added. After that, 2 drops of
2% KMnO4 solution were added quickly.
The test tube was shaked vigorously and the
rate was observed (immediate or slow color
change, or no color change) and extent of
the change in color (violet  brown, violet
 colorless) in the reagent. The test tube
was compared with water as a negative
control. Decolorization of the reagent is
FIGURE 3. Ignited Benzene that shows the immediate when it occurred within 1
greatest amount of soot. minute, the results were noted. The clean up
involved the placement of the products in
In a small evaporation dish, 3-5 drops their respective disposable bottles.
of the sample were placed and a lighted
match was applied. The color of flame 5. Test for Aromaticity (Nitration)
produced was noted which could be bluish,
orangish or yellowish. Also, it was noted
whether the flame is sooty or not. The
burning time was observed, and the results
were jotted down.

4. Test for Active Unsaturation (Baeyer’s

Test)

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FIGURE 5. Adding 2 mL of conc. HNO3 in an A drop of the organic compound was
Erlenmeyer flask. introduced in a dry test tube. 1 drop of 2%
KMnO4 (aq.) was added. Three (3) drops of
Two (2) mL of conc. HNO3 was placed 10% NaOH (aq.) were added after and
in an Erlenmeyer flask. The flask was lastly, 7 drops of water were added. The rate
immersed in an evaporation dish containing (immediate or slow color change, or no
water and 2 mL conc. H2SO4 were added color change) was observed together with
gradually. The resulting mixture was cooled the extent of the change in color (violet 
to room temperature. This served as the green, violet  brown, or violet 
nitrating mixture. Five (5) drops of the colorless) in the reagent. Results were noted.
organic compound were placed in a dry test
tube. Eight (8) drops of the nitrating mixture RESULTS AND DISCUSSION
was added after and the test tube was shook
that ensured complete mixing. Any The results of the experiments were divided
formation of a yellow oily layer was noted. into the different tests each organic
Any yellow oily layer formed could be seen compound was placed on.
when the product was diluted with 20 drops
of water. The clean up involved placing the 1. Physical State, Color and Odor
solution in a large beaker and slowly was
diluted with 20 mL water. Sodium carbonate The physical state of benzene, toluene,
was added until foaming ceases and placed cyclohexene and hexane at room
in an aqueous solution container provided. temperature is liquid. They all appear clear
and have no color. They all exhibit a strong
6. Basic Oxidation odor.

FIGURE 6. Product of Benzene, a drop of 2% FIGURE 7. Toluene is observed to be liquid at

KMnO4 (aq.), 3 drops of 10% NaOH (aq.) and 7 room temperature and appears clear with no
drops of water. color.

2. Solubility in conc. H2SO4

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 cyclohexene exhibit a luminous flame.
Benzene, toluene and hexane are Hexane exhibited little to no soot whereas
immiscible with the conc. H2SO4. These Cyclohexene exhibited little amount of soot.
organic compounds when H2SO4 was added, Benzene and toluene showed the greatest
2 layers are prominent. Cyclohexene is amount of soot when ignited by a lighted
inferred as miscible with H2SO4 because the match referring to figure 10.
resulting product is homogenous referring to
figure 8. This makes cyclohexene aliphatic
and unsaturated.

FIGURE 10. Toluene exhibiting the greatest

amount of soot among the hydrocarbons
FIGURE 8. Product of Benzene and Conc. experimented.
H2SO4 that shows two distinct layers.
4. Test for Active Unsaturation (Baeyer’s
Test)

When 2 drops of 2% KMnO4 solution

were added to Hexane, Benzene and
Toluene, their solutions maintained violet in
color and it can be inferred that there is no
decolorization. On the other hand,
Cyclohexene in the same process resulted to
an immediate color change from a violet
solution to a brown solution referring to
figure 11. This means that Benzene, Hexane
FIGURE 9. Product of Cyclohexene and Conc. and Toluene are inactively unsaturated
H2SO4 that shows a homogenous mixture. compounds while Cyclohexene is an
actively unsaturated compound.
3. Ignition Test
The mechanism involved in obtaining
The 4 hydrocarbons tested are all the positive result of this reaction has got to
flammable. Benzene, toluene, hexane and do with the reduction of the purple

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potassium permanganate to a brown color. This hints that Benzene is inactively
precipitate of manganese oxide. unsaturated.

5. Test for Aromaticity (Nitration)

When the nitrating mixture was added

to the 4 organic compounds, only Toluene
and Benzene formed a distinct yellow oily
FIGURE 11. Chemical equation showing the layer. Cyclohexene and Hexane showed no
reduction of potassium permanganate into yellow oily layer. The 4 organic compounds
manganese oxide. are immiscible with the nitrating mixture. It
can be inferred that the organic compounds
benzene and toluene are aromatic but
cyclohexene and hexane are not aromatic.
The basis of the test of aromaticity is the
formation of a yellow oily layer.

6. Basic Oxidation

Among the 4 compounds tested for

Basic Oxidation, only Cyclohexene
exhibited an immediate color change from
violet to brown. Benzene, Toluene and
FIGURE 12. Product of Cyclohexene and 2
Hexane showed no discoloration and their
drops of 2% KMnO4 that shows an immediate
solutions stayed with a violet color. This
color change of brown and this hints that
Cyclohexene is actively unsaturated. means that among the 4 compounds,
cyclohexene is the actively unsaturated
hydrocarbon and the remaining 3 are
inactively unsaturated hydrocarbons.

FIGURE 13. Product of Benzene and 2 drops of

2% KMnO4 that shows no immediate color
change wherein the solution exhibits a violet

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 the organic compound and not with excess
water left with the undried test tube. It is
also suggested that in experimenting with
hydrocarbons, temperature should be added
as variable and not as a constant since these
organic compounds exhibit different
characteristic because of their differences in
their boiling points.

REFERENCES

FIGURE 14. In the test for Basic Oxidation, [1] Quinkert G, Egert E, Griesinger C
Cyclohexene exhibited an immediate color (1996) Aspects of organic chemistry:
change from violet to brown.
structure. Wiley, New York
[2] Khan Academy (n.d.). Carbons and
CONCLUSION
hydrocarbons. Retrived Novermber 10,
2018, from
Hydrocarbons exhibit a wide range of
https://www.khanacademy.org/science/biolo
characteristics as shown from the
gy/properties-of-carbon/carbon/a/carbon-
experiments. It can be inferred that
and-hydrocarbons
Cyclohexene is miscible with H2SO4 and
[3] Britanica, T. E. (2018). Hydrocarbons.
actively unsaturated based on the basic
Retrieved November 110, 2018, from
oxidation test and Baeyer’s test. Benzene
https://www.britannica.com/science/hydroca
and Toluene are aromatic based on the
rbon
Nitration Test since they formed a yellow
[4] G. Patrick (2004). Organic Chemistry.
oily layer on top of the test tube. Hexane
New York, New York: Garland
showed the least amount of soot in the
Science/BIOS Scientific Publishers
ignition test while Toluene exhibited the
greatest amount of soot.
From Books:
Bettelheim FA, Brown WH, Campbell MK,
RECOMMENDATION
Farrell SO (2008). Introduction to general,
In such experiments that concern
organic and biochemistry. Cengage
observing real-time reactions, quick jotting
Learning, Belmont
down of notes should be observed. Dealing
with these organic compounds is hazardous
and because of this, it is highly advisable to
wear standard PPE to further prevent
accidents. Having dry test tubes will also
make the experiment less likely to have
errors because when placing drops of
reagents, the reagent will solely react with