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Reporter: Cesarah Justine M. Cabungcal Instructor: Engr.

Aldrin Lorrenz Chan


Section: 2 ChE B Date Performed: March 28, 2017
Group No: 2 Date Submitted: April 18, 2017

Experiment No. 7: Analysis of Hydrocarbons


INTRODUCTION
Hydrocarbons are the simplest forms of organic compounds and are formed by a series of
bonds between carbon atoms. These are present in natural gas, crude oil, petroleum, plant life,
and as well as pesticides. The structural appearance of hydrocarbons may vary from branched,
linear, or ring. The structural differences between them affects the conformation, stability, and
how the molecule functions (as shown in figure 1). Formation of isomers are also possible within
hydrocarbons. Molecules that share the same chemical formula but have their atoms connected
differently, or arranged differently in space, are known as isomers. (Khan, 2017).
The goal of this experiment is to conduct
series of qualitative tests to differentiate various types
of hydrocarbons (saturated, unsaturated, aromatic,
etc.), to distinguish hydrocarbon from each type, and
to characterize an unknown hydrocarbon through
parallel chemical tests from the given unknown
sample and three (3) reference standards which are
cyclohexene, toluene, and hexane. There are three (3)
qualitative tests involved in the determination of what
type of hydrocarbon the samples are: Nitration test,
bromine test, and basic oxidation. In nitration test, a
nitrating mixture is to be dropped on the samples
while in bromine test, a bromine reagent is added to
the samples. Potassium permanganate (KMnO4) and
10% NaOH was added in the mixture in the basic
oxidation test. After the addition of aforementioned
reagents and mixture, the color, odor or any changes
that will be occuring should be observed. However, a
set of conditions must first be followed to proceed or
to stop a sample from proceeding to another test. A
sample that has undergone a test and has met the
required result or not can be classified which type of
hydrocarbon it is.
Figure 1: Structural differences of
hydrocarbons
METHODOLOGY
The objective of this experiment is is to conduct series of qualitative tests to differentiate
various types of hydrocarbons (saturated, unsaturated, aromatic, etc.), to distinguish hydrocarbon
from each type, and to characterize an unknown hydrocarbon through parallel chemical tests. To
do so, four (4) test tubes were prepared containing 5 drops sample of the unknown, cyclohexene,
toluene, and hexane. The nitration test was first done on all the prepared samples by adding eight
(8) drops of nitrating mixture and was shaken well. The samples were further heated due to no
immediate change in physical appearance. A yellow oil precipitate will confirm that the sample
has passed the nitration test or not. Moreover, a different set of tests will be followed if the
sample has manifested a yellow oil precipitate (refer to the diagram below as shown in figure 2).

Unknown Sample

NITRATION TEST BROMINE TEST
NO
NO SATURATED
Yellow Colorless
ALIPHATIC ALIPHATIC
oil? soln?

YES

AROMATICS UNSATURATED
ALIPHATIC

BASIC OXIDATION

Brown NON-
ppt? ALKYLATED
NO AROMATICS

YES
AROMATICS
ALKYLATED

Figure 2: Schematic diagram of the tests (nitration test, bromine test, and basic oxidation)
Figure 3: Nitration test Figure 4: Bromine test

Figure 5: Basic oxidation test Figure 6: Water bath set-up


The samples that showed a yellow oil precipitate were toluene and cyclohexene,
therefore, the samples are aromatics (as shown in figure 3) and further proceeds to the basic
oxidation test which are the aliphatics. However, for the cases of the unkown sample and hexane
as having showing no signs of the yellow oil, these samples will proceed to the bromine test. The
next test was the bromine test on the unkown sample and hexane. Every new test to be made
must be done using new set of samples. After preparation of 5 drops of new sample again on the
labeled test tubes, 3 drops of bromine reagent were added. Bromine reagent has a color of
reddish-brown and it has decolorized the samples meaning the unkown sample and hexane
passed the bromine test and has reached a classification of saturated aliphatics (as shown in
figure 4). The remaining samples were yet to be known of what type of hydrocarbon and has
undergone basic oxidation test. Upon the preparation of fresh samples, 3 drops of potassium
permanganate (KMnO4) and 10% NaOH was added and the mixture was placed in a water bath
for 2 minutes (as shown in figure 6). A confirmatory sign of the basic oxidation is the appearance
of a brown precipitate and only the cyclohexene sample manifested a brown precipitate and
classified under alkylated aromatics. A violet color was seen on the mixure was toulene, not a
brown precipitate, therefore it is described as a non-alkylated aromatic (as shown in figure 5).

DATA SHEET
Table 1: Chemical Test Samples
Chemical Time Unkown Reference Standards Procedures Positive
Tests Sample visible
[+] [-] result
Nitration 10 minutes [-] no Toluene Hexane Yellow
test yellow oil oil/ppt
Cyclohexene
was
observed
Bromine 20 minutes [-] no Hexane Reagent
test brown ppt decolorizes:
brown ppt
Basic 5 minutes Cyclohexene Toluene Brown ppt
oxidation
test
TREATMENT OF RESULTS AND DATA
Table 2: Samples and their hydrocarbon classifications
Samples Type of hydrocarbon
Unknown sample Saturated aliphatic
Hexane Saturated aliphatic
Cyclohexene Alkylated aromatics
Toluene Non-alkylated aromatics

DISCUSSION OF RESULTS
Hydrocarbons have four (4) general classes namely alkanes, alkenes, alkynes, and arenes.
The following reference standards used were each of these classes: cyclohexene alkenes,
hexane alkanes, & toluene arenes. The production of yellow oil in the mixture is due to the
nitration of arenes and alkenes. It is confirmed that they are aromatic compounds. The bromine
test showed the reactivity of alkanes to bromine. Bromine only reacts with alkanes or aromatic
hydrocarbons under special conditions. However, bromine reacts readily, and rapidly, with
alkenes to produce dibromoalkanes. A successful reaction is indicated when the reddish-brown
bromine is used up and colorless products are formed (as shown in figure 4 and figure 7). The
appearance of a reddish-brown precipitate indicates that the mixture is a saturated aliphatic.
Aliphatics are hydrocarbons containing carbon and hydrogen joined together in straight chains,
branched trains or non-aromatic rings. Aliphatic compounds may be saturated (e.g., hexane and
other alkanes) or unsaturated (e.g., hexene and other alkene, as well as alkynes) (Helmenstine,
2016).

R R Br Br

C C + Br2 R C C R

R R R R

(reddish) (colorless)
Figure 7: Bromine test reaction

The basic oxidation test showed the reactivity of confirmed aromatic compounds to
potassium permanganate (KMnO4) and were further classified whether the samples were
alkylated or non-alkylated aromatics. Potassium permanganate is an oxidizing agent that can
react with alkenes to form diols, but does not react with alkanes or with aromatic rings. It can
react with alkyl substituents on aromatic rings, but only under very vigorous conditions (high
temperature etc.) A successful reaction will produce a brown precipitate (MnO2), and the purple
color of the potassium permanganate will disappear (as shown in figure 8) (Buckler, 2010).

R R HO OH

C C + 2KMnO4 + 2CH3OH R C C R + 2MnO2 + 2KOCH3


R R R R
(purple) (brown)

Figure 8: Basic oxidation test reaction

The cyclohexene (alkene) produced a brown precipitate which indicates it is an alkylated


aromtic while toluene (arene) manifested only a purple color indicating it is a non-alkylated
aromatic. Aromatic compounds, originally named because of their fragrant properties,
are unsaturated hydrocarbon ring structures that exhibit special properties, including unusual
stability, due to their aromaticity. They are often represented as resonance structures containing
single and double bonds. However, the bonding is stronger than expected for a conjugated
structure, and it is more accurately depicted as delocalized electron density shared between all
the atoms in the ring (Boundless, 2016).

CONCLUSIONS AND RECOMMENDATIONS


Hydrocarbons can be classified into various types using a series of tests. The
determination of the type of hydrocarbon present in the sample is made possible through the
execution of the nitration test, bromine test, and basic oxidation test. Observations made an
essential role in the qualitative tests done because a positive visible result must be seen to
confirm the reactivity of the given sample from the added solvent in the mixture. The structure of
the sample also influenced its reactivity towards specific solvents like nitrating mixture, bromine,
and potassium permanganate. Errors in the visibility of the result can be encountered due to the
impurity of the solvents. To see a much clearer precipitate or changes in the mixture, the
preparation of the solvents must be done well to avoid errors furthermore in the performance of
the experiment.
REFERENCES
[1] Boundless. "Properties of Aromatic Compounds." Boundless
Chemistry Boundless, 20 Sep. 2016. Retrieved 18 Apr.
2017 from https://www.boundless.com/chemistry/textbooks/boundless-
chemistry-textbook/organic-chemistry-23/aromatic-hydrocarbons-
165/properties-of-aromatic-compounds-635-3608/.

[2] Buker, N. (2010). Lab 2: Physical and Chemical properties of hydrocarbons.


Retrieved from 131Nlab2Hydrocarbins.pdf.

[3] Cavida, C. (2010). Experiment 7: Classification tests for hydrocarbons. Formal-


Report-Experiment-7-Classification-test-for-hydrocarbons.pdf.

[4] Experiment 3: Reaction of hyrdocarbons. (n.d.). Retrieved from


http://www.pcc.edu/staff/pdf/662/ch102_exp_3.pdf.

[5] Experiment 9: Qualitative tests for hydrocarbons; unknown hydrocarbon. (n.d.).


Retrieved from http://myweb.brooklyn.liu.edu/swatson/Site/
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[6] Hydrocarbon structures and isomers. (2017). Retrieved from


https://www.khanacademy.org/science/biology/properties-of-
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[8] Rev. (2003). Experiment 3: Hydrocarbons. Retrieved from


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[9] The saturated hydrocarbons: alkanes and cycloalkanes. (n.d.). Retrieved from
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