CHE214L: Organic Chemistry Laboratory University of Santo Tomas

Laboratory Manual (1st Semester: AY 2019 – 2020) Department of Chemical Engineering

Laboratory Safety and Assessment Form

Course: CHE 214L Organic Chemistry Laboratory Group No.:

Experiment No. 7: Analysis of Hydrocarbons

Personnel Involved: undergraduates, laboratory staff, and instructors

Quantity Used
Substances Involved* in Experiment
Hazards and Toxicities Precautions and First Aid

*identify all chemical reagents / substances that you will use in the experiment.

Signed: _____________
Date: _____________

For the exclusive use of University of Santo Tomas Chemical Engineering students.
CHE214L: Organic Chemistry Laboratory University of Santo Tomas
Laboratory Manual (1st Semester: AY 2019 – 2020) Department of Chemical Engineering

Experiment No. 7

ANALYSIS OF HYDROCARBONS

OBJECTIVE
to characterize an unknown organic compound as either saturated aliphatic, unsaturated aliphatic,
alkylated aromatic, or non-alkylated aromatic using chemical analysis

INTRODUCTION
Hydrocarbons are organic compounds that contain only carbon and hydrogen, which can be straight
chain, branched, or cyclic molecules. Hydrocarbons can be further classified as either aromatic or aliphatic.
Cyclic hydrocarbons with structures related to that of benzene are aromatic, otherwise it is aliphatic.
Aliphatic hydrocarbons are divided into three classifications: alkanes have only single bonds; alkenes have
C=C double bonds; and alkynes have C≡C triple bonds. Alkanes are saturated due to the presence of
hydrogen atoms in every possible location, while alkenes and alkynes are both unsaturated.

Utilizing a systematic approach based on the scheme provided, the unknown hydrocarbon will be
classified as either saturated aliphatic, unsaturated aliphatic, alkylated aromatic, or non-alkylated aromatic.
The qualitative tests in this experiment shall illustrate fundamental reactions of the aforementioned
hydrocarbon classifications that give rise to visible indicators, which will aid in deciding for the presence
or absence of a particular hydrocarbon in the sample.

MATERIALS AND EQUIPMENT

1:1 H2SO4-HNO3 nitrating reagent toluene beaker
5% Br2 in CH2Cl2 hexane thermometer
2% KMnO4 (aqueous) cyclohexene test tubes
10% NaOH solution unknown compound droppers

PROCEDURE
Following the schematic diagram in Figure 2, perform chemical tests on the following known compounds
- toluene, hexane, cyclohexene (shown in Figure 1). Classify each compound as either a positive or a
negative reference standard for each test. Refer to these reference standards in deciding whether the
unknown compound yields a positive or a negative result for a particular test. Based on the results, identify
the compound as either saturated aliphatic, unsaturated aliphatic, alkylated aromatic or non-alkylated
aromatic.

For the exclusive use of University of Santo Tomas Chemical Engineering students.
CHE214L: Organic Chemistry Laboratory University of Santo Tomas
Laboratory Manual (1st Semester: AY 2019 – 2020) Department of Chemical Engineering

H3C

CH3
CH3
toluene hexane cyclohexene
Figure 1. Skeletal structure of reference standards

A. Nitration Test

Caution!! The nitrating agent contains sulfuric acid (H2SO4) and nitric acid (HNO3).
Both acids are corrosive and oxidizing. Use the fume hood when working with this reagent.

Note: Using a hot plate, prepare a 50-oC water bath before proceeding with this test.
1. Add 8 drops of 1:1 H2SO4-HNO3 nitrating agent to 5 drops of the sample and shake well.
2. If no visible change appears within 2 minutes, heat the solution in a water bath at 50oC for 8 minutes.
3. Dilute the solution with 20 drops of water.
4. The test yields a positive result if a yellow oil or precipitate is produced. Otherwise, the result is
negative.

B. Bromine Test
1. Add 3 drops of the bromine reagent (5% Br2 in CH2Cl2) to 5 drops of the sample. If the red-brown
bromine reagent decolorizes, add 3-5 more drops of the reagent or until no color change is observed.
2. The test yields a positive result if the reagent decolorizes. Otherwise, the result is negative.

C. Basic Oxidation Reaction

Note: Using a hot plate, prepare a 50-oC water bath before proceeding with this test.
1. Add 3 drops of 2% aqueous KMnO4 and 2 drops of 10% NaOH to 5 drops of the sample.
2. Warm the solution in a water bath at 50oC for 2 minutes.
3. The test yields a positive result if brown precipitates form. Otherwise, the result is negative.

For the exclusive use of University of Santo Tomas Chemical Engineering students.
CHE214L: Organic Chemistry Laboratory University of Santo Tomas
Laboratory Manual (1st Semester: AY 2019 – 2020) Department of Chemical Engineering

Figure 2. Schematic diagram for hydrocarbon characterization

TREATMENT OF RESULTS
1. From the chemical test results, describe your observations and briefly discuss your conclusion on the
hydrocarbon characterization of the unknown sample.

QUESTIONS
1. Describe how hydrocarbons are characterized for each chemical test. Provide general chemical
reactions that explain the appearance of the indicators for each test result (i.e. yellow oil or precipitate
for the nitration test).
2. Name at least two alternative chemical tests that can be performed to characterize hydrocarbons in an
unknown sample. Cite your references.

REFERENCES

Garcia, C. (2014). Laboratory Experiments in Organic Chemistry.

Lancashire, R. J. (2005). Qualitative analysis of organic compounds. Retrieved from

http://wwwchem.uwimona.edu.jm/lab_manuals/c10expt25.html

For the exclusive use of University of Santo Tomas Chemical Engineering students.
CHE214L: Organic Chemistry Laboratory University of Santo Tomas
Laboratory Manual (1st Semester: AY 2019 – 2020) Department of Chemical Engineering

Data Sheet (copy to your respective logbooks)

Experiment No. 7

ANALYSIS OF HYDROCARBONS

Names: ___________________________ Analysis Score: _____________

___________________________ Section / Group No.: _____________
___________________________ Date(s) Performed: _____________

Note: Use the schematic diagram (Figure 2) as guide. You do not need to do all chemical tests for the
unknown hydrocarbon.

Reference Standards Unknown Sample

Chemical Tests (write the known compound) (write either positive or negative;
positive standard negative standard if not done, write N/A)
Nitration Test

Bromine Test

Basic Oxidation Reaction

Conclusion based on results of the chemical tests:

Unknown compound number is a

(sample no.) (type of hydrocarbon)

Observations:

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