Reaction of Hydrocarbons

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 Reaction of Hydrocarbons
Desiree Reagan
Biochemistry Department, College of Allied Sciences,
De La Salle Medical and Health Sciences Institute, City of Dasmariňas, Cavite

03 FEB 2022

ABSTRACT

Hydrocarbons are extremely useful organic compounds in everyday living. Four experiments were performed to understand
the properties of hydrocarbons. For flammability, the substances were placed in a watch glass and lit on fire with a matchstick.
For solubility, the hydrocarbons were mixed with water and food coloring to observe the layers separate or merge. For
bromination reactions, bromine was added to different hydrocarbons in a dark room. The experiment was repeated on
hydrocarbons that did not react by exposing them to sunlight. In cracking hydrocarbons, mineral wool was soaked with
paraffin in a boiling tube. Pumice stones, which served as catalysts, were also placed inside the tube. The tube was heated
back and forth between the catalyst and the paraffin. The escaping gas was collected in six test tubes, and they were tested
for the properties of hydrocarbons. All of the hydrocarbons were flammable and exhibited the expected characteristics of their
combustion. Most of the hydrocarbons were clearly insoluble in water except for cyclohexane. The set-up was a possible
source of error for this result. All of the hydrocarbons followed their expected reactions with bromine. It had four possible
reactions: addition, substitution, free-radical substitution, and no reaction. As for the last experiment, all of the collected gas
displayed the properties of alkanes and alkenes. It had an odor similar to camping gas, a yellow-orange flame, and reacted
with bromine water and potassium permanganate solution.

Keywords: hydrocarbons, flammability, solubility, bromination, cracking

Introduction: hydrocarbons as well as the significance of cracking

Hydrocarbons are organic compounds that only consist of
hydrogen and carbon atoms. They are most commonly
used for fuel in transport and cooking, but they are also
utilized in creating synthetic fabric, plastic packaging, and
construction materials such as asphalt and tar.
Hydrocarbons may be aliphatic or aromatic in nature. The
three types of aliphatic hydrocarbons may be alkanes,
alkenes, and alkynes. Alkanes only contain single bonds,
alkenes contain one or more double bonds between carbon
atoms, and alkynes contain one or more triple bonds
between carbon atoms. Their structure may also be cyclic,
which is when the first and last carbon atoms are
connected to each other. Then, they are called
cycloalkanes, cycloalkenes, and cycloalkynes. Aromatic
hydrocarbons are called as such because of their distinct
fragrance. They contain a benzene ring, which is a six-
carbon ring with three evenly distributed double bonds. The
experiments aim to understand the different properties of
hydrocarbons.
According to Lautenberger et al. (2006), flammability is a
chemical property that measures “the ease with which a
material is ignited, the intensity with which it burns and
releases heat once ignited, its propensity to spread fire,
and the rate at which it generates smoke and toxic
combustion products during gasification and burning.”
When a substance is burning, it means that it is
experiencing combustion. As stated by Dietrich et al.
(2015), “combustion occurs when fuel and oxygen react to
produce carbon dioxide, water, and heat.” Fuel is any
substance that releases its stored energy upon reacting.
The color of the flame may imply its temperature,
completeness of combustion, or type of fuel (Elgas
Administration, 2021). It is well known that the blue flame is
the hottest, followed by white, yellow, orange, and red. Blue
flame signifies complete combustion, while the other colors
signify incomplete combustion. Complete combustion
 1

occurs when there is enough oxygen to react with the smaller, more useful hydrocarbon molecules” (British
carbon and hydrogen atoms to form water and carbon Broadcasting Corporation, n.d.) The initial hydrocarbons
dioxide. Incomplete combustion occurs when there is not are alkanes, while the products of cracking are alkanes and
enough oxygen. Aside from a yellow to red flame, it also alkenes. According to Kumar et al. (2015), paraffins are
produces soot and carbon monoxide gas. In general, “simple straight or branched polymeric chains of
bigger hydrocarbons tend to incompletely combust since hydrocarbons of alkanes with a chemical composition of
more oxygen is required for the reaction. Double and triple CnH2n+2.” When potassium permanganate solution is
bonds between carbons also require more energy to break. mixed with the products of cracking a paraffin, the alkene is
This increases the probability of incomplete combustion. oxidized because its C-C double bond is broken and is
replaced with two C-O double bonds. Thus, the solution will
Solubility is defined as the amount of solute that forms a either become brown or colorless. As various small
saturated solution in a specified amount of solvent and hydrocarbons are in demand, cracking helps meet the
temperature (Soult, 2020). A substance dissolves in a demand by breaking down large hydrocarbons that are not
solvent when the solute-solvent interactions overcome the largely sought after in the market.
solute-solute and solvent-solvent interactions. That is why
polar or ionic solutes are best soluble in polar solvents Objectives:
while nonpolar solutes are best soluble in nonpolar
solvents. Hydrocarbons are composed of nonpolar covalent After the completion of the four experiments, students will
bonds; therefore, it is expected that they are insoluble in have the ability to:
polar solvents and soluble in nonpolar solvents.
Hydrocarbons also do not contain fluorine, oxygen, or 1. understand the hydrocarbons’ flammability and
nitrogen, which means that they cannot hydrogen bond solubility properties;
with water.
2. recognize the kind of hydrocarbon in relation to
Hardinger (2017) defines bromination as a reaction their reactivity with specific reagents;
where only bromine is introduced into a molecule. As a
reagent, bromine is a strong electrophile that is useful for 3. determine the products of a hydrocarbon reaction;
examining the reactivity of colorless nucleophilic organic and
compounds due to its maroon color. If there is a reaction,
4. comprehend the cracking of hydrocarbons.
the solution will turn colorless instead of maroon.
Electrophiles are attracted to their electron-rich Methodology:
counterparts, which are the nucleophiles. Bromination
reactions may be addition or substitution. In addition For the experiment on the flammability of hydrocarbons,
reactions with alkenes, two C-Br bonds are formed in the a Pasteur pipette is first used to transfer hydrocarbons with
product. In substitution reactions, one C-Br bond is formed an amount of one-fourth of a bulb draw onto a watch glass.
in the product while the other bromine combines with
hydrogen to form hydrogen bromide gas. This gas is easily
detected when it reacts with ammonia and forms a cloud of
ammonium bromide particles. Double bonds increase the
nucleophilicity of the reactant because of the presence of a
pi bond. However, if the pi bonds are evenly distributed like
a benzene ring, then it will lead to a lower electron density
due to its delocalized electrons, thereby failing to attract the
bromine. Methoxy substituents, which are functional groups
that contain a methyl group bonded to oxygen, also Figure 1.1. Transferring a sample hydrocarbon
increase nucleophilicity through increasing electron density
by virtue of its lone pairs on the electronegative oxygen Next, it is lit on fire with a burning matchstick.
atom. Alkanes have no pi bonds, but they are able to react
with bromine under sunlight in a free-radical substitution
reaction because the UV light provides enough energy to
separate the bromine molecule into two reactive radicals
through homolysis. This type of bond cleavage happens
when each atom gets an unpaired electron.

Cracking a hydrocarbon is “a reaction in which larger

saturated hydrocarbon molecules are broken down into
Figure 1.2. Igniting a sample hydrocarbon

Finally, data and observations were recorded. The
hydrocarbons tested in this experiment were cyclohexane,
cyclohexene, and toluene.
The second experiment was about the solubility of
hydrocarbons. Four test tubes were prepared with the
same amount of water.
Figure 2.1. Initial setup of experiment
Each test tube was added their specific compound
(water, cyclohexane, cyclohexene, and toluene) using a
Pasteur pipette until they all had the same lower meniscus
level.
Figure 2.2. Adding of hydrocarbons
Two drops of water-based red food coloring were added
to each test tube.
Figure 2.3. Adding of food coloring
Finally, data and observations were recorded.
2
The third experiment tested the reactivity of different
hydrocarbons (cyclohexane, cyclohexene, benzene,
anisole, and toluene) with bromine. The hydrocarbons were
placed in beakers in a dark room. Two drops of bromine
were added to each beaker.
Figure 3.1. Adding of bromine to sample hydrocarbons
For anisole, there was an adjacent beaker containing
ammonium hydroxide to detect if hydrogen bromide gas
was released.
Figure 3.2. Introduction of ammonium hydroxide
For cyclohexane, its reactivity was tested again by
exposing it to sunlight after bromine was added. Similar to
anisole, there was also a beaker with ammonium hydroxide
ready.
Figure 3.3. Introduction of sunlight
Finally, data and observations were recorded.
 3

The fourth experiment showed the cracking of long-chain

hydrocarbons. First, mineral wool was placed in the bottom
of a boiling tube.

Figure 4.4. Clamping the tube to prepare for heating

Approximately 15 pieces of pumice stone were placed in

Figure 4.1. Placing of mineral wool inside tube the tube, and it was tilted to an almost horizontal orientation
so that the catalyst does not fall to the bottom.
A dropping pipette was used to add liquid paraffin in
order to soak the mineral wool until its size was around 2
cm3. The wet mineral wool was pushed down with a stirring
rod to aid its absorption.

Figure 4.5. Addition of catalyst

A bung with a delivery tube was attached to the mouth of

the boiling tube.
Figure 4.2. Pushing down mineral wool soaked with
paraffin

Next, the tube was inverted to see if there was any

excess. If there was an excess, a pipette would have been
used to remove it.

Figure 4.6. Attachment of delivery tube

One bowl with six submerged test tubes and bungs was
filled with water.

Figure 4.3. Inverting of boiling tube

The tube was clamped near its mouth.


Figure 4.7. Setup for collecting of gas
The pumice stones inside the boiling tube were heated
with the hottest part of a roaring Bunsen flame.
Figure 4.8 Heating of boiling tube.
The escaping gas in this process was collected in a test
tube.
Figure 4.9. Process of collecting gas.
The pumice stones were heated for ten seconds. Then,
the paraffin soaked in the mineral wool was briefly heated
before the catalyst was kept hot again. This action of
heating back and forth between the catalyst for ten
seconds and the paraffin for one second was repeated until
six test tubes of gas were collected. If signs of suck-back
were exhibited, the boiling tube would have been heated
until all of the water was removed. To end the experiment,
the delivery tube was removed from the bowl of water while
the boiling tube was still being heated. Once there was no
more water in the tube, heating was also stopped.
4
Figure 4.10. Process of removing water from delivery tube
Next, the tubes were tested for their properties. The first
two test tubes were discarded because they were just air
from the boiling tube. The third tube was observed for its
smell. The fourth tube was ignited to see if it was a
flammable gas. The fifth tube was added drops of bromine
water and shaken up to check its reactivity. The sixth test
tube was added acidified potassium permanganate to also
check its reactivity.
Figure 4.11. From left to right, top to bottom: (1) two test
tubes are discarded, (2) third test tube’s smell is observed,
(3) fourth test tube is ignited, (4) fifth test tube is mixed with
bromine, (5) sixth test tube is mixed with potassium
permanganate solution
Finally, the Bunsen burner was turned off, and
observations were recorded.
 5

Results and Discussions:

In the first experiment, all of the hydrocarbons were

flammable as expected since they can react with oxygen to
undergo combustion.

Table 1.1. Table of reactants and their flammability

characteristics

Compound Flammability
Figure 5.2. Extremely sooty flame of toluene
Cyclohexane Flammable, yellow-orange flame, with soot
The color of isooctane’s flame was blue with traces of
Cyclohexene Flammable, yellow-orange flame, with yellow, and it had no observable soot, which signifies that it
more soot was a nearly complete combustion.

Toluene Flammable, orange-red flame, with most

soot

Isooctane Flammable, mostly blue with a bit of yellow

flame, no observable soot

As seen in Table 1.1, the differing amounts of soot

reinforced the aforementioned relationship between
incomplete combustion and the number of bonds. The
alkanes, cyclohexane and isooctane, produced the least
soot, followed by the alkene, cyclohexene, and the
aromatic hydrocarbon, toluene. Cyclohexene only has one
double bond and six carbons, while toluene has three
double bonds and seven carbons.
Figure 5.3. Almost complete combustion of isooctane
Although isooctane and cyclohexane are both alkanes,
cyclohexane did not exhibit a blue flame despite not having
double or triple bonds and having fewer carbon atoms than
isooctane.

Figure 5.1. Moderately sooty flame of cyclohexene

Figure 5.4. Mildly sooty flame of cyclohexane
Thus, it was expected that toluene would produce the
A possible reason for this discrepancy is that the setup
most soot out of all the compounds.
for isooctane and cyclohexane was different. Isooctane
was prepared in a gallon with sufficient oxygen, while
cyclohexane was only placed on a watch glass.
 6

The second experiment tested the hydrocarbons’

solubility in water. As a polar compound, water was soluble
in water.

Figure 6.2. From left to right: (1) clear distinction between

water and cyclohexene, (2) defined boundaries of water
and toluene, (3) blurry division between water and
cyclohexane

A possible source of error is that the tube containing the

cyclohexane was not shaken, stirred, or even rotated to
Figure 6.1. The mixture is completely red with no distinction
provide a clearer view of the result.
between the layers of water
In the third experiment, all hydrocarbons behaved as
Hydrocarbons are insoluble in water because they are
expected.
nonpolar and are not capable of hydrogen bonding.
Table 3.1. Table of reactants and their reaction with
Table 2.1. Table of reactants and their solubility in water
bromine in a dark room
Compound Solubility in Water
Compound Reaction with Br2 in a Dark Room
Water Soluble
Cyclohexane
Cyclohexane Partially Soluble

Cyclohexene Insoluble
Cyclohexene
Toluene Insoluble

Octane Insoluble
Benzene

Cyclohexene, toluene, and octane fulfilled these

expectations. However, the cyclohexane seemed slightly Anisole
partially soluble even though it should have been insoluble.
When comparing the results of cyclohexane with the other
hydrocarbons, it did not have a clear distinction between
the two layers. Instead, it looked like a blurry division Toluene
between the layers.
 7

The alkene, cyclohexene, went through an addition Table 3.2. Table of reactants and their reaction with
reaction. The presence of a lone pi bond increased the bromine under sunlight
nucleophilicity because of the higher electron density.
Compound Reaction with Br2 under Sunlight

Cyclopentane

Toluene

Figure 7.1. Addition reaction turns the solution colorless

The anisole, which contained a methoxy group, had a Benzene

substitution reaction. It also released hydrogen bromide
gas which reacted with ammonia in the prepared
ammonium hydroxide solution.

As previously mentioned, alkanes can react with bromine

under sunlight through a free-radical substitution reaction.
The bromine radicals with one electron each substituted
the place of the hydrogen to form a bromination product
and hydrogen bromide gas. Thus, it is only right that the
monobromination product of cyclopentane with bromine
was bromocyclopentane.

Figure 7.2. In substitution reaction, a cloud of ammonium

bromide particles is formed, and the solution turns colorless

The alkane, cyclohexane, did not react because it did not

have pi bonds to attract the bromine. Both benzene and
toluene did not react because of their lowered electron
density due to the benzene ring.

Figure 7.4. In free-radical substitution reaction, solution

turns colorless when exposed to sunlight, and a cloud of
ammonium bromide particles is collected

Toluene was able to react with bromine under sunlight,

while benzene still did not have any reaction. This is
because the substitution reaction of bromine with toluene
took place in the methyl side chain. Therefore, the benzene
ring was not the reacting site. This also explains why the
Figure 7.3. No reaction makes the solution orange
benzene compound still did not react with bromine at all.
Unresponsive reactants were tested again to react with
bromine in a different setup. Instead of taking place in a
dark room, they were tested again under sunlight.
 8

The observations on the test tubes in the fourth

experiment were in line with the known properties of the
expected products: alkanes and alkenes.

Table 4.1. Table of collected test tubes and their observed

characteristics

Test Tube Observations

#1 Only air from boiling tube; discarded

Figure 8.2. Solution in fifth test tube turned colorless due to
#2 Only air from boiling tube; discarded addition reaction of bromine and alkene

#3 Smell of camping gas - a mixture of propane The solution in the sixth test tube became colorless,
and butane which signifies that an alkene was oxidized by the acidified
potassium permanganate.
#4 Flammable gas, yellow-orange flame, no
observable soot

#5 Reacted with bromine; solution became

colorless

#6 Reacted with acidified potassium

permanganate; solution became colorless

The color of the flame in the fourth test tube is similar to

the color of the alkanes and alkenes in the first experiment,
cyclohexane and cyclohexene. It also has no observable
soot; however, it was only ignited for a very short period of
time, so there is a possibility that it could have produced
soot if given more time.
Figure 8.1. Fourth test tube was lit on fire
Bromine reacted in the fifth test tube, which proves the
presence of an alkene since it did not have to be exposed
to UV light in order to react.
Figure 8.3. Solution in sixth test tube turned colorless due
to potassium permanganate solution
Conclusions:
All in all, the experiments were able to showcase the
different properties of hydrocarbons and the process of
cracking. Most of the experiments led to expected results;
however, there were possible sources of error in some of
the tests. In the flammability experiment, the two alkanes
did not have the same setup. In the solubility experiment,
the cyclohexane was not stirred, shaken, or rotated for a
better perspective. As for the paraffin experiment, the
fourth test tube was not ignited long enough to observe the
possible formation of soot. Aside from fixing the possible
sources of error, some recommendations to improve the
accuracy of experimental results include specifying the
amounts of all the substances used and keeping the same
setup for all substances in the same experiment.
 9

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