Experiment 1: Alkanes, Alkenes, Alkynes

A. Calangi1, J. Melchor1, A. Pangilinan1

1 Departmentof Physical Sciences, College of Science, UP Baguio, Baguio City 2600
Performed 31 January 2020; Submitted 5 February 2020

ABSTRACT

Hydrocarbons are organic compounds that are composed of only carbon and hydrogen atoms. There are three
main classes of hydrocarbons, namely alkanes, alkenes, and alkynes. The main difference between the three is
the type of bond – single, double, or triple – they possess. Their differences in chemical reactivities rely on
these bonding types. The laboratory experiment aims to characterize hydrocarbons based on the type of bonds
present between carbon atoms through chemical reactions such as combustion and bromine light testing. The
results in the combustion reaction showed that butane gas and acetylene differ in the type of flame produced,
blue flame without soot and yellow flame with visible soot, respectively, due to carbon percentage inequality
between saturated and unsaturated carbons. In the bromine test, butane and acetylene showed no evidence of
changes in color in the absence of light, except ethylene because of its double bonds. On the contrary, all the
gases displayed positive results under the exposure of sunlight.

Introduction hydrocarbons based on their chemical properties

and reactivity through the combustibility test and
Hydrocarbons are organic compounds that contain bromine test. In combustibility test, the
only carbon and hydrogen atoms. They are hydrocarbon is ignited, and the flame produced is
generally insoluble in water because of its non- observed. On the other hand, the bromine test
polarity. Based on the number of bonds between detects the presence of unsaturation or phenols in
carbon atoms, hydrocarbons can be classified as the compound and the positive result is a change in
alkanes, alkenes, and alkynes (McMurry, 2019). color of the solution (Bettelheim & Landesberg,
Alkanes have at least one single bond of carbon and 2000).
is referred to as saturated compounds because
each carbon contains the maximum number of Methodology
hydrogen atoms that a carbon can possess. The
primary source of alkanes are natural gas and In this experiment, two different tests were
petroleum. The smaller alkanes—methane, ethane, performed—the combustibility test and bromine
propane, and butane—are gases under ambient light test.
conditions (Solomons & Fryhle, 2009).
The combustion analysis was performed to both
Conversely, alkenes contain at least one carbon- butane (C4H10), an alkane, and acetylene (C2H2), an
carbon double bond. One of the simplest alkenes is alkyne. Butane gas from the lighter was collected
ethene, which is highly flammable and explosive by water displacement method and placed into
(Pohanish, 2011). Alkynes, on the other hand, three test tubes. The same method was applied in
contain at least one carbon–carbon triple bond. The collecting acetylene from calcium carbide, which
simplest alkyne is ethyne (also called acetylene). was also placed into three test tubes. The last
Both alkene and alkyne are called unsaturated collected samples of butane and acetylene were
compounds because they hold less than the used in the combustibility test, where the brim of
maximum number of hydrogen atoms, and they are each test tube was ignited, and the flame produced
capable of reacting with hydrogen under the was observed.
proper conditions (McMurry, 2019).
The second test through the reaction with bromine,
There are various ways to identify hydrocarbons. with and without light, was also performed to
This experiment aims to differentiate butane and acetylene. The last two samples of
butane and acetylene were both subjected to Br2 The ignition of the last collected butane sample
light test by adding 20 drops of Br2 solution with produced a blue flame without any visible soot on
water to each test tube; one of which was covered the brim of the test tube. The occurrence of blue
with an aluminum foil while the uncovered test flame was due to the low carbon content of butane
tube was exposed to sunlight. After 10 minutes, the (McMurry, 2019) and sufficient amount of oxygen
change in color of the solutions was observed. The from the air, allowing the compound to go undergo
same test was conducted to ethylene (C2H4), an complete combustion. Complete combustion
alkene, which was collected by cutting a happens when carbon and hydrogen atoms are
polyethylene bag into small pieces and placed completely oxidized to produce only carbon
inside a shaped aluminum foil. The open end of the dioxide and water (Mishra, 2017). The complete
foil was then inserted to a test tube containing 20 combustion of butane is given by the equation:
drops of Br2 solution with water, and heat was
2C4H10 + 13O2 → 8CO2 + 10H2O
applied to the foil. The change in color of the
solution was observed. The same procedure was
Butane undergoing complete combustion
repeated using a wrapped test tube with 20 drops
correlates with the observation that there was no
of Br2 solution with water.
soot produced. The formation of soot is dependent
on the insufficiency of oxygen. Oxygen, being
Results and Discussion
severely restricted, impedes the gas from going
through complete combustion. Instead, it proceeds
The primary objective of this laboratory
to incomplete combustion. This type of combustion
experiment is the characterization of the three
yields water, carbon monoxide, and carbon atoms.
classes of hydrocarbons – alkanes, alkenes, and
The fine particles of carbon are soot (Brown &
alkynes. The main difference of the three is
Lufaso, 2017). Since there were no soot formed, it
determined by the type of bond they form. The
suggests that the compound went to complete
bonding affects the chemical reactivities of the
combustion, instead of incomplete.
compounds. In order to differentiate the
hydrocarbons using their chemical properties, the
On the contrary, a yellow flame with visible soot
most common tests – combustion and reaction to
was observed after igniting acetylene. The
bromine with and without light – were performed.
appearance of a yellow flame with visible soot was
due to the lack of oxygen (Hahn, 2019). Low
A. Combustibility Test
percentage of oxygen hinders the complete
oxidation of carbon, resulting in incomplete
The samples of butane and acetylene were
combustion – which is characterized by a yellow
obtained, from butane lighter and calcium carbide
flame (Greiner, 1997). Incomplete combustion of
respectively, by using water displacement. This
acetylene was observed through the formation of
method allowed the acquisition the compounds
soot. Soot is produced by fine particles of carbon
mainly because of the densities of the liquid
from carbon monoxide and water – products of
(water) and gases (butane and acetylene) present
incomplete combustion (Brown & Lufaso, 2017).
in the setup. The density of a matter as compared
The incomplete combustion of acetylene is given
to another determines which will rise and sink.
by the equation:
Since gases generally have lower densities than
liquids (Myers, 2003), there is a tendency for the 2C2H2 + 3O2 → 4CO + 2H2O
particular gas to accumulate inside, impelling the
water out of the test tube. Three samples were B. Bromine Test
collected from each gas. Using the last collected
samples of butane and acetylene after its collection The bromine test was used to differentiate alkanes,
by water displacement was crucial since the other alkenes, and alkynes, specifically butane, ethylene,
samples already mixed with air; if any of those and acetylene, in a bromine solution by observing
were ignited, it would result to explosive reactions. the color changes, that indicate different chemical
reactivities of gases.
Two samples of butane and acetylene from the electrophilic addition. In this process, one of the
previous collection of gases were utilized. One test bromine atoms will be attached to the carbon
tube from each was covered with aluminum foil atoms, forming a bromonium ion. The bromonium
and was then left inside the room, while placing the ion will then be attacked by bromide ion (Clark,
unwrapped test tube outside, exposed to sunlight. 2019). During these series of reactions, the double
Meanwhile, two samples of ethylene were acquired bonds of ethylene, causing the changes in color --
from a polyethylene bag. Hydrocarbon gases, such from yellow to clear. The equation below
as ethylene, can be extracted from plastics during summarizes the halogenation of ethylene:
high-temperature decomposition (Royer, Ferrón,
Wilson, Karl, & Pardha-Saradhi, 2018). In this CH2=CH2 + Br2 → CH2—CH2
experiment, the polyethylene bag was cut into
pieces and was then placed inside a foil. The foil Br Br
was then subjected to heat by using the alcohol
lamp, allowing the collection of ethylene by the Acetylene has the same reaction as butane in the
decomposition of the polymer. The color changes in bromine light test. The wrapped test tube did not
different bromine solutions were noted. show any color changes, while the sample exposed
to light also displayed evident alteration in color –
The sample of butane, wrapped with an aluminum turning clear. The occurrence of color change in the
foil and left inside the room for 10 minutes, showed solution is due to addition reactions, similar to
no changes in color. The observation is due to the alkenes. A nucleophilic alkyne will cause the
absence of light. According to Sheehan (1964), polarization of a halogen molecule. The reaction of
substitution by halogens, in this case – bromine, is the pi electrons of an alkyne and bromine will form
negligible without ultraviolet light (UV light). This a carbon-bromine bond and cyclic halonium ion
corresponds to the reaction of the gas upon being with halide as the leaving group (Clark, et al, 2019).
exposed to sunlight. The bromine solution The changes in color is due to the breaking of triple
containing butane turned into lighter yellow. The bonds to form carbon-bromine bond. The equation
process of photohalogenation is responsible for the below summarizes the halogenation of acetylene:
slight changes in color. In the photohalogenation of
alkanes, UV light will split halogen molecules into Br Br
halogen atoms. These atoms will then cleave the Br Br
carbon-hydrogen bond of an alkane, leaving an Br3 Br3
H-C≡C—H C=C Br—C—C—Br
alkyl and a hydrogen halide. Haloalkanes will be
produced due to the alkyl splitting another halogen H H
H H
molecule. Another halogen will react to another
alkane molecule. Series of chain reactions will Conclusion and Recommendations
occur until the termination step where only desired
product will be left (Breitmaier, 2016). Essentially, Observations
photohalogenation is also a substitution reaction Test Reaction with Bromine
(Ramsden, 2001). In the case of butane, a carbon- Compound Combustibility with without
+/- +/-
light light
hydrogen bond was broken, causing the slight Blue flame
Lighter No
change in color, to form a carbon-bromine bond. Butane without any
yellow
+
reaction
-
visible soot
The equation below summarizes the halogenation
Ethylene NA Clear + Clear +
of butane: Yellow flame
No
Acetylene with visible Clear + -
reaction
soot
CH4 + Br2 → CH3Br + HBr Figure 1. Summary of the results of combustibility and
bromine tests
For ethylene, there was both discoloration of the
liquid, with and without the presence of light. The As shown in figure 1, butane produced a non-sooty
reaction of alkenes with bromine is light blue flame which implies the low percentage of
independent. The solution turning clear on both carbon in butane, as a saturated hydrocarbon, and
the absence and presence of light is due to is completely oxidized by the oxygen present in air.
On the other hand, acetylene, an unsaturated Hahn, E. (2019). Blue Flame vs Yellow Flame vs
hydrocarbon, produced a sooty yellow flame due to Red Flames - Gas Flame Color. Retrieved from
incomplete combustion. https://www.elgas.com.au/blog/1585-why-
does-a-gas-flame-burn-blue-lpg-gas-natural-
Likewise, both butane and acetylene manifested a propane-methane
negative result under the bromine test without
light. This concedes to the concept of halogenation Greiner, T. H. (1997, September). Carbon Monoxide
which states that when the hydrocarbon and Poisoning: Checking for Complete Combustion.
halogen reactants are not exposed to UV light or Retrieved from
heat, the reaction does not occur (Clayden et. al., https://www.abe.iastate.edu/extension-and-
2001). Nevertheless, once a reaction is started, the outreach/carbon-monoxide-poisoning-
light or heat source can be removed, and the
checking-for-complete-combustion-aen-175/
reaction will continue. This explains why ethylene,
even without light, showed a positive result in
Royer, Ferrón, Wilson, Karl, & Pardha-Saradhi.
reaction with bromine. On that premise, it is
(2018). Production of methane and ethylene
recommended to ensure that the solution is well-
wrapped before starting the test. from plastic in the environment. Public Library
of Science, 13(8). doi:
Furthermore, in bromine test with light, all of the 10.1371/journal.pone.0200574
hydrocarbons exhibited a positive result. Butane,
however, exhibited a slight change in color due to Sheehan, W. (1964). Chemistry, a Physical
factors such as the low intensity of light; hence, it is Approach. Allyn and Bacon.
recommended to expose the sample under intense
sunlight, or high intensity light. Breitmaier, E. (2016). Efficiently Studying Organic
Chemistry: For Students of Chemistry,
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