CHM142L Organic Chemistry 1 Laboratory

2nd Quarter SY 2013-2014

Preparation and Characterization of Hydrocarbons

Miranda, Marilyn1, Salen, Vladimir, A.2
Miranda, Marilyn, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; 2Salen, Vladimir A., CHM142L/B22, School of Chemical
Engineering, Chemistry and Biotechnology, Mapua Institute of Technology
1

ABSTRACT
In this experiment, we are expected to prepare and characterize unsaturated and saturated hydrocarbons. Hydrocarbons are
compounds that contain carbon and hydrogen atoms only. They are generally classified as alkanes, alkenes, alkynes and
aromatic hydrocarbons. Alkanes are those that do not contain functional groups. Alkenes are those that contain C-C double
bonds. Alkynes are those that contain C-C triple bonds. Aromatic hydrocarbons are those that contain the aromatic ring. The
main purpose of this experiment are (1) to differentiate alkanes, alkenes, alkynes and aromatic hydrocarbos through their
properties, (2) to visualize the characteristic reaction of alkanes, alkenes, alkynes and aromatic hydrocarbons and (3) to
prepare acetylene gas.The main point of the methodology is recording your observation as best / accurate as you can. In order
to perform this experiment we used the reagents such as benzene, cyclohexene, cyclohexane, concentrated sulphuric acid,
calcium carbide and potassium permanganate while the materials used are micro test tubes, pipet, iron clamp, iron stand,
evaporating dish and water trough. There different test to distinguish hydrocarbons such as flammability test, bromination,
oxidation and ammoniacal silver nitrate test.Flammability test is used to distinguish between saturated and unsaturated
hydrocarbons as unsaturated produced black sooty flame when burned and saturated hydrocarbons produced no soot when
subjected to combustion. Saturated hydrocarbons will only react with bromine under free radical conditions, meaning you
have to add UV light. So simply adding some bromine to cyclohexane wont cause a reaction to occur. Observation and proper
preparation of the compound is the key point of this experiment and depends on how you analyze the your obtained result. The
results of the experiment has a good observation and satisfactory results.
Keywords: Hydrocarbons, Flammability test, Bromination, Oxidation, Ammoniacal siver nitrate test, saturated and unsaturated.

INTRODUCTION
Hydrocarbons are compounds that contain carbon
and hydrogen atoms only. They are generally classified as
alkanes, alkenes, alkynes and aromatic hydrocarbons.
Alkanes are those that do not contain functional groups.
Alkenes are those that contain C-C double bonds. Alkynes
are those that contain C-C triple bonds. Aromatic
hydrocarbons are those that contain the aromatic ring.
Hydrocarbons may be differentiated in terms of
their physical and chemical properties. Among the more
useful physical properties that distinguish hydrocarbons are
flammability and solubility. Compounds that are
unsaturated, such that, those that have C-C multiple bonds
usually produce a black sooty flame when burned. This is
primarily due to imcomplete combustion which results in the
formation of unburned carbon residues. Saturated
compounds, on the other hand, produce no soot when
subjected to combustion.
The hydrocarbons may also be identified as
lacking solubility in water. Hydrocarbons are not capable of
forming hydrogen bonds with water due to lack of hydrogen
atoms attached to oxygen, nitrogen or fluorine.

Experiment 07 Group No. 1December 3, 2013

The aliphatic unsaturated hydrocarbons generally

undergo addition reactions. Examples of addition reactions
include bromination and addition of sulphuric acid. These
reactions do not require any catalyst and may therefore
occur even at low temperatures and in the dark. Alkanes
undergo bromination only when heated or in the presence
of light via a mechanism known as free-radical substitution.
Aromatic hydrocarbons, while unsaturated, do not undergo
addition reactions as such reactions would disrupt the
stability of the aromatic ring.
Alkenes and alkynes easily undergo oxidation
reactions even under very mild conditions. Examples of
oxidizing agents that may be used to distinguish alkenes
and alkynes from other hydrocarbons include potassium
permanganate, chromatic acid, and osmium tetraoxide. The
aromatic compounds are not oxidized at room temperature.
Terminal alkynes, or those that have a hydrogen
atom attached to a carbon in a C-C triple bond, may be
identified by using reactions that take advantage of the
acidity of the terminal hydrogen. The terminal hydrogen is
slightly acidic due to the electronegativity of the sp-

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hybridized carbon atom in alkyne. Examples of bases that

may react to terminal alkynes are ammoniacal silver nitrate
and sodium metal.
The main purpose of this experiment are (1) to
differentiate alkanes, alkenes, alkynes and aromatic
hydrocarbos through their properties, (2) to visualize the
characteristic reaction of alkanes, alkenes, alkynes and
aromatic hydrocarbons and (3) to prepare acetylene gas.
MATERIALS AND METHODS
In determining the flammability of alkane, alkene
and aromatic hydrocarbons, the reagents needed are
cyclohexane, cyclohexene and benzene and the material
are three evaporating dish. First, (1) place two drops of the
test compounds in an evaporating dish. (2) Ignite the
compound using a match. (3) Note whether the compound
is flammable or not. If flammable note the color of the flame
produced. Finally, (4) Record your observations.
In determining the solubility of alkane, alkene and
aromatic hydrocarbons, the reagents needed are
cyclohexane, cyclohexene and benzene and the material
are three micro test tubes. First, (1) place two drops of each
of the test compounds in separate micro test tubes. (2) Add
1 mL of distilled water. Shake. (3) Note whether the test
compounds are miscible or immiscible. Finally, (4) Record
your observations.
In determining the reactions of alkane, alkene and
aromatic hydrocarbons by bromination, the reagents
needed are cyclohexane, cyclohexene, benzene and 1.0M
bromine in carbon tetrachloride and the materials needed
are three micro test tubes. First, (1) place 2 drops of each
of the test compounds in separate micro test tubes. (2) Add
drop by drop with shaking freshly prepared 1.0 M bromine
in CCl4 until a change is observed. (3) Record your
observation. Finally, (4) Give the equation involved in the
reaction.
In determining the reactions of alkane, alkene and
aromatic hydrocarbons by oxidation, the reagents needed
are cyclohexane, cyclohexene, benzene and 1.0M solution
of potassium permanganate and the materials needed are
three micro test tubes. First, (1) place 2 drops of each of the
test compounds in separate micro test tubes. (2) Add drop
by drop with shaking 1.0 M solution of potassium
permanganate. (3) Observe the solution for 2 minutes. (4)

Experiment 07 Group No. 1December 3, 2013

Record your observation. Finally, (5) Give the equation

involved in the reaction.
In determining the reactions of alkane, alkene and
aromatic hydrocarbons by sulfuric acid test, the reagents
needed are cyclohexane, cyclohexene, benzene and
concentrated sulfuric acid and the materials needed are
three micro test tubes. First, (1) place 2 drops of each of the
test compounds in separate micro test tubes. (2) Add 0.50
mL of concentrated sulfuric acid. (3) Observe whether heat
is released from each test tube. (4) Record your
observation. Finally, (5) Give the equation involved in the
reaction.
In preparation of acetylene, the reagents needed
is calcium carbide and the materials needed are 8-in test
tube, cork, rubber tubing and water trough. First, (1) place
2.0 g calcium carbide inside an 8-in test tube (this will serve
as the generation tube). (2) Clamp the generation tube 450
in an iron stand. (3) Pour 10 mL of distilled water into the
tube and stop up it with a cork having a rubber tubing long
enough to extend into a small water reservoir (water
trough). Note: The reservoir should contain 5 micro test
tubes submerged in water. Have 5 small corks ready to
stopper the generated gas. (4) Collect the acetylene gas via
downward water displacement method (the instructor will
demonstrate this method). The first tube should be
discarded. Finally, (5) Save the test tubes containing the
gas for characterization.
In determination of properties of acetylene by
ammoniacal silver nitrate test, the reagents needed are
acetylene gas, ammoniacal silver nitrate solution,
concentrated sulfuric acid and the material needed is test
tube. First, (1) get one of the test tubes containing the
previously generated acetylene gas. (2) Carefully transfer 1
mL of freshly prepared ammoniacal silver nitrate solution in
the test tube. (3) Note the reaction that took place. (4)
Record your observation. (5) Give the equation involved in
the reaction. Note: Discard the solution by adding 1 mL of
concentrated sulfuric acid. Shake the solution until all the
solids are dissolved. Set aside the solution for 5 minutes. If
the solid remains undissolved, gently heat the solution.
Allow the solution to cool down before discarding it using
plenty of water.
In determination of properties of acetylene by
bromination, the reagents needed are acetylene gas and
1.0M potassuim permanganate solution and the material is
test tube. First, (1) get one of the test tubes containing the

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previously generated acetylene gas. (2) Carefully transfer 1

mL of 1.0 M KMnO4 solution in the test tube. (3) Note the
reaction that took place. (4) Record your observations.
Finally, (5) Give the equation involved in the reaction.
In determination of properties of acetylene by
oxidation, the reagents needed are acetylene gas and 1.0M
potassium permanganate and the material needed is test
tube. First, (1) get one of the test tubes containing the
previously generated acetylene gas. (2) Carefully transfer 1
mL of 1.0 M KMnO4 solution in the test tube. (3) Note the
reaction that took place. (4) Record your observations.
Finally, (5) Give the equation involved in the reaction.
RESULTS
Table 7.1: Physical Properties of Alkane, Alkene and
Aromatic Hydrocarbons

precipitate
formed

Reactions
with conc.
H2SO4 (3)

No heat
released;
the color
remain
unchanged

precipitate
formed and
immiscible
to each
other
Heat
released;
the color
changed to
dark brown
solution
become
dried

and
immiscible
to each
other.
No heat
released;
the color
remain
unchange
d;
immiscible

Reaction Involved

Observations
Properties

Cyclohexane

Cyclohexene

Flammabilit
y

Flammable;
Yellow

Flammable;
Orange
with little
sooty black

Solubility

Immiscible

Immiscible

Benzene
Flammable

; Orange
with
sooty
black

(1a)

Immiscible

Table 7.2: Reactions of Alkane, Alkene and Aromatic

Hydrocarbons

Reactions
Brominatio
n (1)

Oxidation
(2)

Cyclohexa
ne (a)
The color
changed
from
colorless to
golden
yellow

The color
changed
from
colorless to
purple and

Observations
Cyclohexe
ne (b)
The color
changed
from
colorless to
golden
yellow and
back to
colorless
The color
changed
from
colorless to
black and
black

Experiment 07 Group No. 1December 3, 2013

(1b)

Benzene
(c)
The color
changed
from
colorless
to golden
yellow

The color
changed
from
colorless
to black

(1c)

(2a)

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Observations and Reactions Involved

(2b)

The test tube was positioned downward and the water

replacement with gas took place. The first replacement
was discarded. The succeeding ones where stored.
In the reaction between calcium carbide and
water, acetylene gas is produced:

(2c)

CaC2(s) + 2H2O(l) Ca(OH)2(s) + C2H2(g)

The rapid oxidation of acetylene by oxygen
produces its combustion products of carbon
dioxide and water.
2C2H2(g) + 5O2(g) 4 CO2(g) + 2H2O(g) +
heat

(3a)

Table 7.4: Reaction of Ammoniacal Silver Nitrate,

Bromination and Oxidation on Acetylene

Reactions

Observations

Ammonical Silver
Nitrate (1)

The ammoniacal silver nitrate

produce white precipitate as it
mix with acetylene gas
The color of the bromide
solution change from golden
yellow to light brown to
colorless as it mix with
acetylene gas
The color of the potassium
permanganate solution
changed frompurple to brown
as it mix with acetylene gas

(3b)

Bromination (2)

Oxidation (3)
(3c)

Reaction Involved

2AgNO3+ C2H2

Ag2C2+ 2HNO3

2
Table 7.3: Preparation of acetylene gas

Experiment 07 Group No. 1December 3, 2013

3 C2H2 + 2 KMnO4 + 4 H2O

3 C2H2(OH)2

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+ 2 MnO2 + 2 KOH 3
DISCUSSION
Flammability test is used to distinguish between
saturated and unsaturated hydrocarbons as unsaturated
produced black sooty flame when burned and saturated
hydrocarbons produced no soot when subjected to
combustion. The unsaturated hydrocarbons produce a
black sooty flame when burned due to incomplete
combustion which the result in the results in the formation
of unburned carbon residue.
The forces that hold molecules together in a liquid,
solid and solution phases are very weak. They are
generally called London dispersion forces. The electrons in
the orbitals of a molecule are free to move around. If you
could compare a "snapshot" of the molecule at an instant in
time, you would see that there would be slightly different
charge distributions caused by the different positions of the
electrons in the orbitals. The amount of difference is based
on the polarizability of the molecule, which is a measure of
how well electrons can move around in their orbitals. In
general, the polarizability increases as the size of the orbital
increases; since the electrons are further out from the
nucleus they are less strongly bound and can move about
the molecule more easily. When two molecules come
together, these variations in charge can create a situation
where one end of a molecule might be slightly negative and
the other end of that molecule could be slightly positive.
This would result in a slight attraction of the two molecules
(until the charges moved around again) but is responsible
for the attractive London dispersion forces all molecules
have. These London dispersion forces are weak, the
weakest of all the intermolecular forces. Their strength
increases with increasing size and polarizability of the
molecule. On the other hand, the rule to use when
determining hydrocarbon solubility is: Like dissolves like.
This means that polar compounds (water, alcohols, and
carboxylic acids) dissolve other polar compounds. Water
can be broken down into H - OH, thus it has the -OH group
which identifies alcohol and carboxylic acids. Nonpolar
compounds dissolve other nonpolar compounds but tend
not to dissolve polar compounds. When you test for
solubility you are looking for either a homogeneous solution
or a heterogenous solution. Homogeneous solutions have
no layers evident indicating the hydrocarbon being tested is
soluble. These hydrocarbons are miscible. Heterogenous

Experiment 07 Group No. 1December 3, 2013

solutions have layers evident indicating the hydrocarbons

are insoluble. These hydrocarbons are immiscible.
Based on the reaction involved on Table 7.2:
Reactions of Alkane, Alkene and Aromatic Hydrocarbons,
Saturated hydrocarbons will only react with bromine under
free radical conditions, meaning you have to add UV light.
So simply adding some bromine to cyclohexane wont
cause a reaction to occur. Aromatic hydrocarbons can react
with bromine only in the presence of a strong Lewis acid
catalyst such as FeBr3. So simply adding some bromine to
benzene wont cause a reaction to occur. Cyclohexene will
readily reacts with bromine .
Another reaction that alkenes undergo is oxidation.
When a purple solution of the oxidizing agent KMnO is
added to an alkene, the alkene is oxidized to a diol and the
KMnO is converted to brown MnO. Thus, if the purple color
changes to brown in this reaction, it is a positive reaction.
The chemical test used to distinguish 1-pentyne
and 2-pentyne is addition of ammoniacal silver nitrate
solution as 1-pentyne gives white precipitate with
ammoniacal while 2-pentyne does not. In distinguishing 1pentyne and 1-pentene, addition of ammoniacal silver
nitrate solution would give white precipitate with 1-pentyne
and not with 1-pentene, thats why addition of ammoniacal
silver nitrate solution is appropriate chemical test. In
distinguishing cyclohexane and cyclohexene, flammability
test is the simple test to used as cyclohexene produce liitle
sooty black flame while cyclohexane dont. In distinguishing
1,3-cyclohexadiene and benzene, addition of concentrated
sulfuric acid is appropriate as heats of hydrogenation would
reflect the relative thermodynamic stability of the
compounds. In practice, 1,3-cyclohexadiene is slightly more
stable than expected, by about 2 kcal, presumably due to
conjugation of the double bonds. However, benzene is an
extraordinary 36 kcal/mole more stable than expected. This
sort of stability enhancement is now accepted as a
characteristic of all aromatic compounds. Lastly, in
distinguishing cyclohexane and benzene, flammability test
is the best as benzene produce sooty black flame and
cyclohexane dont.
CONCLUSIONS AND RECOMMENDATIONS
In the experiment, it is successful to differentiate
alkanes, alkenes, alkynes and aromatic hydrocarbons
through their properties such as flammability and solubility
as the unsaturated and saturated hydrocarbons
distinguished by using flammability and solubility test.

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It is also successful to visualize the characteristic

reaction of alkanes, alkenes, alkynes and aromatic
hydrocarbons by bromination, oxidation and adding
concentrated sulphuric acid. In bromination, there was a
change in color when bromine solution is added to different
hydrocarbons. In oxidation, there was a precipitate formed
when potassium permanganate is added in different
hydrocarbons. Lastly, there was a heat released on different
cycloalkene but no heat released cycloalkanes and
benzene when added on different hydrocarbons.
It is also successful to prepare the acetylene gas.
In preparing acetylene gas, the test tube was positioned
downward and the water replacement with gas took place.
The first replacement was discarded. The succeeding ones
where stored.

Experiment 07 Group No. 1December 3, 2013

It is experiment , I recommend that proper

attention and observation on the reaction will lead to
satisfactory result. Observation is the key point of this
experiment and depends on how you analyze the your
obtained result.
.REFERENCES
1. Baluyot, J.Y. G. and De Castro, K. Organic Chemistry
Laboratory Manual for Chemical Engineering Students, Part
1, Mapua Institute of Technology, Manila, Philippines

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