CHM142L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

Preparation and Characterization of Hydrocarbons

Terrado, Rence Christian L.

Professor Marilyn Miranda, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; Bote,Jairus Lemuel ; Brillas, Catherine Jill
CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology

ABSTRACT
The organic compounds cyclohexane, cyclohexene, benzene, and toluene were subjected to
different physical and chemical tests to differentiate their intrinsic physical properties and
chemical properties in terms of structure and behavior. The aim of this experiment is to (1) to
differentiate alkanes, alkenes, and aromatic hydrocarbons through their properties (2) to visualize
the characteristics reactions of alkanes, alkenes, alkynes, and aromatic compounds and also (3)
to prepare (acetylene gas). The physical state, color, and odor were noted by simple physical
observation. Miscibility was tested by introducing a drop of the sample to water and concentrated
H2SO4. Flammability was tested by placing 2-4 drops of the sample to an evaporating dish and
lighting it with a match. Active unsaturation was tested using the Baeyers and Bromine test and
aromaticity was determined by subjecting the organic compounds to Nitration. Oxidation was
tested by introducing drops of KMnO4 solution and 3 drops of 10% NaOH solution to 4 drops of the
sample organic compound in a test tube. All organic compounds showed immiscibility in
concentrated H2SO4 and flammability in the ignition test. All but cyclohexane were not actively
unsaturated. All turned out to be aromatic compounds except cyclohexane and cyclohexene. All
are not oxidized except cyclohexene.
Keywords: Benzene, Cyclohexane. Baeyers test, hydrocarbons
INTRODUCTION H2C
CH3
Hydrocarbons are compounds that contain only Figure 2. Saturated Hydrocarbon
carbon and hydrogen atoms. Hydrocarbons
may be divided into two large classes namely: Cyclohexane is a cycloalkane with the
Saturated hydrocarbons and Unsaturated molecular formula C6H12, molar mass of 84.160
hydrocarbons. Saturated hydrocarbons are the g/mol, and boiling point of 80.74C. It is used
simplest type of organic compounds. They are as a non-polar solvent and a raw material for
hydrocarbons in which all carbon-carbon bonds the production of adipic acid and caprolactam.
are single bonds. An example of a saturated Cyclohexane is produced on an industrial scale
hydrocarbon is an alkane. Unsaturated by reacting benzene with hydrogen.
hydrocarbons are hydrocarbons that contain
one or more carbon-carbon multiple bonds like
double bonds, triple bonds, or both. Saturated
and Unsaturated hydrocarbons have similar
physical properties, but their chemical Figure 3. Cyclohexane

properties are different. Unsaturated

Cyclohexene is a cycloalkane with a chemical
hydrocarbons are chemically more reactive
formula of C6H10, molar mass of 82.143 g/mol,
than saturated ones. This is because of the
and a boiling point of 82.98C. It is not very
presence of carbon-carbon multiple bonds in
stable upon long term storage and exposure to
such compounds and these multiple bonds
light and air should be distilled before use to
serve as locations were chemical reactions can
eliminate peroxides. It has a very sharp smell
occur.
resembling an oil refinery.

CH4
Figure 4. Cyclohexene
Figure 1. Unsaturated Hydrocarbon

Experiment 07 Group No. 4 Date 12/05/14 1 of 5

 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015
Benzene is an organic chemical compound with
a molecular formula of C6H6, molar mass of
78.11g/mol, and a boiling point of 80.1C. It is
a colorless, highly flammable. It is a known
carcinogen, therefore its role as an additive in
gasoline is now limited, though it is an
important industrial solvent and a precursor in
the production of drugs, plastics, synthetic
rubber, and dyes.
Figure 5. Benzene
The miscibility is determined by the weight
percentage of the hydrocarbon chain. The
solvent used in the experiment is concentrated
H2SO4. If a compound is unsaturated, it is said
to be easily sulfonated, or possesses a
functional group containing oxygen, it will
dissolve in sulfuric acid. Alkanes, cycloalkanes,
and their halogen derivatives are insoluble in
sulfuric acid. Simple aromatic hydrocarbons
and their halogen derivatives do not undergo
sulfonation and are also insoluble in sulfuric
acid. Nevertheless, the presence of two or
more alkyl groups on the aromatic ring permits
the compound to be sulfonated easily. Many
secondary and tertiary alcohols are dehydrated
readily by concentrated sulfuric acid, which
results tothe formation of olefins which then
undergo polymerization. The polymers formed
are insoluble in concentrated sulfuric acid and
forms a distinct layer on top of the acid.
Baeyers test is a test for the presence of
unsaturation (double bonds). A similar test can
be done using bromine. Baeyers test uses a
solution called the Baeyers reagent, which is a
solution of alkaline potassium permanganate.
Reaction with double or triple bonds in an
organic material causes the color to fade from
purplish-pink to brown. Easily oxidized
compounds like aldehydes, formic acid and its
esters, alcohols with trace of impurities,
phenols, and thio ethers give positive results.
Quantitatively, the iodine value is used to
determine the presence of unsaturation. The
oxidation was tested using potassium
permanganate. Potassium permanganate is an
inorganic compound and a very strong
oxidizing agent. It is used in the determination
of the total oxidizable organic material in an
Experiment 07 Group No. 4 Date 12/05/14
aquaeous sample. The value determined is
known as the permanganate value.
The objectives of the experiment are: (1) to
differentiate alkanes, alkenes, and aromatic
hydrocarbons through their properties (2) to
visualize the characteristics reactions of
alkanes, alkenes, alkynes, and aromatic
compounds and also (3) to prepare acetylene
gas.
MATERIALS AND METHODS
The part one of the experiment entitled
Physical Properties of Alkane, Alkene, and
Aromatic Hydrocarbons, the group did the
following procedures for testing cyclohexane,
cyclohexene and benzene. First is to test its
flammability, first step is two drops of the
compounds are placed in the evaporating dish
and then ignited using a match. Flames were
observed. Second test done is the solubility of
the compound, first step is to place two drops
of each compound in a micro test tube and
added 1 mL of distilled water then observed
the solubilities if the compound is miscible or
not.
In part two of the experiment entitled
Reactions of alkane, alkene and aromatic
hydrocarbons, the group followed the following
procedures for bromination test. First is two
drops of each hydrocarbons were placed in
micro test tubes then added drop by drop of
1.0 M bromine in CCl4 and observed its reaction
and changes. The group did the same
procedures for Oxidation test and Sulfuric Acid
test but it depends on the concentration of the
reagents used.
In part three of the experiment entitled
Acetylene because acetylene gas was used in
the experiment, the group did the following
procedures. The preparation of acetylene gas
was done by the lab assistant and gaseous
properties and reactions were obtained by
bromination test, Silver nitrate test, and
oxidation test. The same procedure was
followed in the bromination test in part two
which the reagents in the micro test tube are in
liquid form. Ammonical Silver Nitrate test was
done by obtaining one test tube containing
acetylene gas and transferring 1 mL of freshly
prepared ammonical silver nitrate in the test
2 of 5
 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015

tube. Observations were noted. In oxidation Bromina Colorless to Orange to Colorle

process. Acetylene gas was mixed with KMnO4 tion redish lighter ss to
to determine its reaction. orange orange/yel Orang
low e
The apparatuses used in the experiment are
the following: 8-in test tube for preparing Oxidatio
acetylene gas, iron clamp, evaporating dish, n
small corks for cover, micro test tubes, 2.0 mL
pipette, water trough, and iron stand while the Reaction Red/Violet Settled at Not
reagents used are: benzene, cyclohexene, with the Solubl
cyclohexane, calcium carbide, concentrated some bottom e
-formed
H2SO4, 1.0 M Br2 in CCl4, and 1.0M KMnO4 H2SO4 layers

Conc. -gets hot -Smoke, Layere

H2SO4 gets hot d
RESULTS and DISCUSSIONS (strong -
dehydrat Layered(Up -Brownish (Upper
In the experiment, many tests are done to ing per- black -
know the physical properties of organic reagent) colorless; Colorle
compounds and to differentiate the Bottom- ss;
characteristic reactions of different organic orange)
compounds like alkenes, alkynes, and aromatic Botto
compounds. m-
light
Here shows the table that contains the orange
compounds and their properties )

Table 1. Compounds and their Physical

properties Flammability the measure of the extent to
which a material or a substance will support
Properties Cyclohex Cyclohex Benzen combustion. The degree of difficulty required to
ane ene e cause the combustion of a substance is subject
to quantification through fire testing or ignition
Flammab Less - Sooty test. Vapour pressure is an important
ility sooty parameter in determining the ease of ignition
of a substance or material. The higher the
Solubility Immiscibl Immiscibl Immisci vapor pressure, the more flammable vapour is
e e ble evolved from a free liquid surface at a given
temperature. Many compounds are determined
by the characteristics of their flame when they
burn. Aromatic hydrocarbons burn with a
yellow, sooty flame due to their high carbon
content. Aliphatic hydrocarbons, saturated or
unsaturated burn with flames that are yellow,
but less sooty.

Hydrocarbons are non-polar. Water is polar. So

from like dissolves like you wouldnt expect
any of these three to be very soluble in water.
In fact, unsaturated and aromatic
Reaction Cyclohexan Cyclohexe Benze hydrocarbons are slightly soluble in water- the
s e ne ne solubility of benzene in water is ~1500mg/L
not very much. Cyclohexene is even less than

Experiment 07 Group No. 4 Date 12/05/14 3 of 5

 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015
that. Cyclohexane is completely insoluble in
water. 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.
Baeyers test is a test for the presence of
unsaturation (double bonds). A similar test can
be done using bromine. Baeyers test uses a
solution called the Baeyers reagent, which is a
solution of alkaline potassium permanganate.
Reaction with double or triple bonds in an
organic material causes the color to fade from
purplish-pink to brown. Easily oxidized
compounds like aldehydes, formic acid and its
esters, alcohols with trace of impurities,
phenols, and thio-ethers give positive results.
Quantitatively, the iodine value is used to
determine the presence of unsaturation.
Aromaticity is the special stability of planar,
cyclic, fully conjugated molecules with 4n + 2
electrons. Such molecules have orbital systems
with all bonding molecular orbitals completely
filled with all anti-bonding and nonbonding
orbitals empty. The criterion for a compound to
be aromatic is expressed by the Huckels rule.
The oxidation was tested using potassium
permanganate. Potassium permanganate is an
Experiment 07 Group No. 4 Date 12/05/14
inorganic compound and a very strong
oxidizing agent. It is used in the determination
of the total oxidizable organic material in an
aquaeous sample. The value determined is
known as the permanganate value.
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 toluene wont
cause a reaction to occur. Cyclohexene will
readily reacts with bromine. Potassium
permanganate reacts with anything
unsaturated. KMnO4 reacts with alkenes to
form vicinal diols. KMnO4 will also react with
alkyl benzenes, such as benzene, to form
benzoic acids. Although I dont think any
reaction will take place without adding heat.
Alkanes wont react with KMnO4.
CONCLUSIONS AND RECOMMENDATIONS
In this lab experiment, the group determined
some of the physical properties of
hydrocarbons which
After subjecting all 3 organic samples to
different physical and chemical tests, it was
observed that all 6 organic samples were
flammable and immiscible in concentrated
H2SO4. All except hexane produced soot when
ignited. Only cyclohexene behaved as an
actively unsaturated hydrocarbon. All were
aromatic compounds except cyclohexane and
cyclohexene. The only compound oxidized was
cyclohexene.
REFERENCES
1. Shriner, Hermann, Morill, et. Al. 2004.
TheSystematic Identification of
OrganicCompounds. John Wiley and Sons Inc.
2. Hornback, J.M. 1998. Organic
Chemistry.Brooks/ Cole Publishing Company,
Pacificgrove. p.p 816-817
3. L. Gattermann, Die Praxis des organischen
Chemikers, 40th ed., de Gruyter & Co., Berlin,
1961, pp 260-261.
4 of 5
 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015

Experiment 07 Group No. 4 Date 12/05/14 5 of 5