Department of Pure and Applied Chemistry

College of Arts and Sciences

Visayas State University
Visca, Baybay City, Leyte, Philippines, 6521

Name: Eugene L. Codis Date Performed: 02/26/19 & 3/5/19

Laboratory Instructor: M.A. Villar Date Submitted: April 5, 2019

Experiment 5
HYDROCARBONS

Introduction
The simplest organic compounds are called hydrocarbons and contain only the carbon and
hydrogen elements. Although they consist of only two types of atoms, there is a wide variety of
hydrocarbons as they may consist of varying chains lengths, branched chains, and carbon atom
rings, or combinations of these structures. Furthermore, the types of carbon-carbon bonds present
in their molecules may differ from hydrocarbons. In plants, animals and their fossils, many
hydrocarbons are found; other hydrocarbons have been prepared in the laboratory.
Every day we use hydrocarbons, mainly as fuels such as natural gas, acetylene, propane,
butane, and the main components of petrol, diesel fuel, and heating oil. Hydrocarbons are also the
familiar plastics of polyethylene, polypropylene, and polystyrene. Differences in bonding between
carbon atoms that include alkanes, alkenes, alkynes, and aromatic hydrocarbons can distinguish
several types of hydrocarbons.
Alkanes, or saturated hydrocarbons, contain only one carbon atom covalent bond. Each of
an alkane's carbon atoms has hybrid sp3 orbitals and is bonded to four other atoms, each of which
is either carbon or hydrogen. Organic compounds containing one or more double or triple bonds
between carbon atoms are described as unsaturated and alkenes are called unsaturated
hydrocarbons.
Hydrocarbon molecules are called alkynes with one or more triple bonds; they form another
series of unsaturated hydrocarbons. Two carbon atoms attached to each other by a triple bond are
linked together by one π bond and two π bonds. Aromatic hydrocarbons have a cyclic molecule
consisting of carbon and hydrogen with single and double bonds alternating delocalized carbon-
carbon, resulting in increased stability.
Objectives
 To identify the different types of hydrocarbons.
Methodology
The liquid hydrocarbon samples were examined and each compound was subjected to the
tests described below.
A. Ignition Test
Three (3) drops of each hydrocarbon were placed in a porcelain cover and brought with
crucible tongs to the edge of a burner flame. All observations were recorded regarding each
sample's flammability and the nature of the flame (color and sootiness).

B. Reaction with Bromine

One (1) mL of 0.1 M Br2 in CCl4 solution was placed into each of 2 test tubes, one
tube wrapped in carbon paper to protect the contents from light. Three (3) drops of the
sample were added to each tube with stopper, and shaken gently to mix. The unwrapped
tubes were then compared to the contents of the two test tubes for fading Br2 after about
10 minutes. Where fading occurred, the presence of HBr was tested by adding 10 drops of
distilled water to the final mixture and the water layer was tested using litmus paper. The
findings have been recorded.

C. Reaction with Cold Dilute Permanganate

One (1) mL of dilute KMnO4 solution was placed in a test tube, adding 5 drops of the
sample and shaking to mix. The tube content was examined after 5 minutes of intermittent
shaking.

D. Reaction with Ammoniacal Silver Nitrate Solution

The silver reagent was placed in a clean, small test tube with ten (10) drops and added
with 2 drops of hydrocarbon. The tube contents were thoroughly mixed and observed. Any
precipitate obtained by the laboratory instructor was transferred to a vessel.

E. Preparation and Testing of Acetylene Gas

Approximately 5 g of calcium carbide limps were inserted into a dry 250-mL distilling
flask and the rest of the acetylene generation set-up was assembled. Approximately 100
mL of water was added to the dropping funnel, then a few drops were allowed to fall on
the solid and waited for the air to be removed from the apparatus for a few minutes. The
gas evolved was used to test B, C and D to add water when necessary. The gas was bubbled
for a full minute through the test tube contents, wherever the hydrocarbons were added to
the procedure.
Results and Discussion
Table 1. Ignition Test
Samples Sootiness Flammability Color
Cyclohexane No soot Flammable Orange
Cyclohexene Less soot Flammable Light Orange
Acetylene Sooty Flammable Yellow
Benzene Sooty Flammable Yellow
Toluene Sooty Flammable Yellow

When burned, Cyclohexane gave off the yellow color and there was no soot present. This
was because cyclohexane is saturated hydrocarbon, meaning all carbon bonds are single bonds.
When ignited, cyclohexene and acetylene also produced yellow flame but, due to the presence of
unburned carbon, soot was present after burning. Aromatic compounds with a higher ratio of
carbon to hydrogen, such as benzene and toluene, burn with a yellow - orange and sooty flame that
is also the result of unburned carbon particles.

Table 2. Reaction with Bromine in CCl4

Test with Litmus Test with Litmus
Wrapped No Wrap
Samples (Wrapped) (No Wrap)
Test Tube Test Tube
Blue Red Blue Red
Dark color
Light color
Cyclohexane red
red
Turned Remained Turned Remained
Cyclohexene Clear Clear
red red red red
Dark color
Acetylene
red Light red

Dark color
Benzene
red Dark red

Dark color
Toluene
red Light red

The bromine test is a qualitative test for the presence of aniline, phenols and unsaturation.
Only cyclohexene showed Br2 fading out of the five samples in the reaction with the bromine part
of the experiment. Since cyclohexane has only single carbon-carbon bonds, there has been no
bromine reaction as it cannot add bromine. Alkanes are very unreactive, but in the presence of
ultraviolet light they can be brominated.

In an electrophilic reaction, cyclohexene reacts with bromine. The approaching pi bond in

cyclohexene polarized bromine, which was a "polarizable" molecule, inducing a dipole in the
bromine molecule. One of the bromine atoms is attached to both carbon atoms, with the bromine
atom having the positive charge. A bromonium ion was formed at that time. A bromide ion formed
in a nearby reaction, forming a 1,2-Dibromocyclohexane and HBr as a by-product, then attacked
the bromonium ion from the back. The blue litmus paper turned red while the red litmus paper
remained red when the final reaction mixture was added with 10 drops of distilled water and tested
with litmus paper. This indicates that because of the presence of HBr the mixture is acidic.

Acetylene in the wrap test tube did not react while acetylene had a slight color fading in
the test tube without wrap. Due to their aromacity, possession of a closed loop of electrons,
aromatic compounds such as benzene and toluene do not react with the bromine. Although they
have double carbon-carbon bonds, they do not react because aromatic rings are less reactive to
bromine-like electrophiles than alkenes or alkynes. Aromatic rings do not favor electrophilic
addition as the stability will be lost. They require a catalyst to react like iron filings or aluminum
chloride. Benzene and toluene Pi bonds contain delocalized electrons located in the double bonds
above and below the two carbon atoms. This creates a region of high density of electrons.

Table 3. Reaction with Cold Dilute Permanganate

Samples Observations Reaction

Cyclohexane No change Negative
Cyclohexene Substance turned dark brown Positive
Acetylene Brown color Positive
Benzene No change Negative
Toluene No change Negative
 The Baeyer's reagent was a cold Potassium permanganate alkaline solution, a powerful
oxidant, making it a redox reaction. Only cyclohexene and acetylene reacted to form a brown
precipitate when each sample was added to 1 mL of potassium permanganate and shaken for 5
minutes while cyclohexane, benzene and toluene remained as violet-colored solutions. Because
alkanes are saturated hydrocarbons, cyclohexane had no color change and the solution remained
violet with no layers formed. Potassium permanganate therefore does not react with it.

Cyclohexene reacted with the Baeyer's reagent changing the violet-colored solution into
brown due to the reaction with the double bond in the organic compound. The decolorization of
the violet solution and the formation of a brown precipitate (MnO2) is considered as a positive
result. This redox reaction lowers Mn7+ to Mn4+ and oxidizes the alkene to a diol. Alkenes '
reaction to KMnO4 yields a diol and MnO2.
With KMnO4, acetylene reacted to form a diol and a brown precipitate, magnesium oxide.
The presence of the triple bond had a major impact on the reactivity of acetylene so that it changed
from violet to brown in the presence of permanganate. In addition, acetylene is unsaturated; it is
possible to react to oxidation with KMnO4.

When the Baeyer's reagent added benzene and toluene, the solution's color remained violet.
Although aromatic rings are unsaturated, they do not react with KMnO4. Compared to acetylene,
they are relatively stable, causing them not to oxidize in the presence of KMnO4.

Table 4. Reaction with Ammoniacal Silver Nitrate Solution

Samples Observations
Cyclohexane Formed 2 layers
Cyclohexene Bubble formation with 2 layers
Acetylene Bubble formation with 2 layers
Benzene Formed 2 layers
Toluene Formed white precipitate

To determine the presence of a triple bond, the reaction with Ammoniacal Silver nitrate
was done. Only acetylene had a positive reaction from the five samples indicated by white
precipitate formation. In the reaction, the alkyne's terminal proton was released so that the
acetylide ion with Ag+ could form an insoluble precipitate. Acetylene reacted with AgNO3's
ammonia solution, forming silver acetylide.

Because the ammonia silver nitrate reaction was exclusive to alkynes, cyclohexane,
cyclohexene, benzene, and toluene resulted in a negative test where no reaction occurred.

Conclusion
The simplest organic compounds consist of just two elements: carbon and hydrogen. These
are called hydrocarbons. Aliphatic hydrocarbons and aromatic hydrocarbons are separated into two
types. Aliphatic hydrocarbons are C chains - based hydrocarbons. There are three types of
hydrocarbons that are aliphatic. Alkanes are aliphatic, covalent - only hydrocarbons. They are also
referred to as saturated hydrocarbons because, according to covalent bond rules, they have the
maximum number of H atoms possible. Alkenes are aliphatic hydrocarbons containing a double
bond of at least one C - C. They are called unsaturated hydrocarbons because they have fewer than
the highest possible number of H atoms. Alkynes are aliphatic hydrocarbons with a triple bond of
C - C. Similarly, alkynes, except their names end in –yne, are also called unsaturated hydrocarbons.
Sometimes there are aliphatic hydrocarbons with a ring of C atoms, called cycloalkanes (or
cycloalkenes or cycloalkynes). When burned, saturated hydrocarbons do not produce any soot.
Due to the incomplete combustion that takes place during burning, unsaturated hydrocarbons
produce soot when ignited. Due to the higher carbon to hydrogen ratio, incomplete combustion
results from lack of oxygen during combustion. In the form of soot, unburned carbon is observed.
Aromatic hydrocarbons, like benzene, are flat ring systems that consistently overlap p
orbitals. Electrons in the benzene ring have special energetic properties which give physical and
chemical properties of benzene which differ markedly from alkanes. Originally, the term aromatic
was used to describe this compound class because it was especially fragrant. The term aromatic in
modern chemistry denotes the presence of a very stable ring which gives a molecule different and
unique properties.
Hydrocarbons are rather unreactive, but some classical chemical reactions involve them.
The most common reaction to carbon dioxide and water is the combustion reaction of hydrocarbon
with oxygen. It is accompanied by energy release and is our society's primary source of energy
production. Halogens also react in an additional reaction to alkenes and alkynes. Chemical
reactions such as halogenation and oxidation are helpful in predicting the type of hydrocarbon
being tested, saturated or unsaturated.
Answers to Questions
1. Balance the following reactions:
a. Cyclohexane + 9O2 → 6CO2 + 6H2O
b. Cyclohexene + Br2 → C6H10Br2
c. Cyclohexene + Br2 → C6H10Br2
d. Cyclohexene + KMnO4 → 3C6H12O2 + 2MnO2 + 2KOH
e. CaC2 + H2O → C2H2 + Ca (OH)2
f. Acetylene + AgNO3 → Ag2C2 + 2HNO3
g. Acetylene + Br2 in CCl4 → C2H2Br4
h. Acetylene + KMnO4 → H2CCOOK + MnO2

2. Describe the Baeyer’s test for unsaturation. What is a glycol?

The Baeyer unsaturation test is designed to determine the presence of double or triple
carbon bond. Diluted Potassium permanganate is used to oxidize the double or triple
bond carbon-carbon. It is called oxidation because a hydroxyl group replaces the double
bond. The charge of the carbon ranges from + 1 to + 2 in order to lose an electron. A
diol is replaced by an alkene. There is evidence of the reaction because the violet
potassium permanganate has become colorless. A glycol is a compound that attaches
two groups of hydroxyls to different atoms of carbon.

3. Differentiate the hydrocarbons under study in terms of:

a. Hybridization of carbon
Hydrocarbons Cyclohexane Cyclohexene Acetylene Benzene Toluene
Hybridization sp3 sp2 sp sp2 sp3 (Methyl
group)
2
sp (Benzene
ring)

b. Geometry
Hydrocarbons Geometry
Cyclohexane Tetrahedral
Cyclohexene Trigonal Planar
Acetylene Linear
Benzene Trigonal Planar
Toluene Trigonal Planar Tetrahedral
(Benzene ring) (Methyl group)
c. Bond angle
Hydrocarbons Cyclohexane Cyclohexene Acetylene Benzene Toluene
Bond angle 109.5° 120° 180° 120° 109.5°
(Methyl
group)
 120°
(Benzene
ring)
d. Reactivity
Hydrocarbon Cyclohexane Cyclohexene Acetylene Benzene Toluene
Reactivity Unreactive Reactive Reactive Unreactive Unreactive

REFERENCES:
Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry.

https://www.chemguide.co.uk/mechanisms/elsub/nitration.html

https://chem.libretexts.org/Textbook_Maps/Organic_Chemistry/Supplemental_Modules_(Organic_Che
mistry)/Arenes/Reactivity_of_Arenes/Nitration_and_Sulfonation_of_Benzene

(n.d.). Retrieved April 5, 2019, from www.enotes.com/homework-help/write-balanced-equation-

complete-combustion-hexane-264002
Baeyer's Test. (2007, October 22). Retrieved April 5, 2019, from The Physics Van:
https://van.physics.illinois.edu/QA/listing.php?id=505&t=baeyers-test
(n.d.). Retrieved February 21, 2019, from www.enotes.com/homework-help/write-balanced-
equation-complete-combustion-hexane-264002
Baeyer's Test. (2007, October 22). Retrieved April 5, 2019, from The Physics Van:
https://van.physics.illinois.edu/QA/listing.php?id=505&t=baeyers-test
Reaction of Cyclohexene with Bromine and Potassium Permanganate. (2009, March 13).
Retrieved April 5, 2019, from Chemistry Online:
chem2all.blogspot.com/2009/03/reaction-ofcyclohexene-with-bromine.html?m=1
Experiment: Combustion test of saturated and unsaturated hydrocarbons. (2010). Retrieved April
5, 2019, from All About Alkenes: https://alkenes.wordpress.com/2010/02/01/experiment-
combustion-test-of-saturated-and-unsaturated-hydrocarbons/amp
Ball, D. W., & Key, J. A. (n.d.). Hydrocarbons. Retrieved February 26, 2019, from BCcampus:
https://opentextbc.ca/introductorychemistry/chapter/hydrocarbons-2/