Experiment 3

Properties of Hydrocarbons

Objectives
During this lab, students will:
 Observe the chemical properties of alkanes, alkenes, and aromatic compounds
 Classify an unknown hydrocarbon as an alkane, alkene, or aromatic compound by its
chemical properties
 Familiarize with the reactions that are characteristic of the principal types of hydrocarbons

Introduction
HYDROCARBONS can be divided into four groups: alkanes, alkenes, alkynes, and aromatic
compounds. ALKANES are compounds that have only single bonds between their carbon
atoms. ALKENES have at least one double bond between their carbon atoms. ALKYNES have at
least one triple bond between their carbon atoms. AROMATIC COMPOUNDS are based on
BENZENE, a six-carbon ring with alternating single and double bonds. Each class of
hydrocarbons has its own chemical properties.
In this lab, you will observe five types of reactions: hydrocarbons with bromine, acidified
permanganate, alkaline permanganate, concentrated sulfuric acid, and in combustion. You will
use cyclohexane, cyclohexene, and toluene as your alkane, alkene, and aromatic, respectively.
You will use the observations you make with these hydrocarbons to determine whether three
unknown liquids are alkanes, alkenes, or aromatic compounds.

Pre-lab Questions
Answer the questions on the last page of this document BEFORE the lab session and submit
your answers to your instructor upon entry into the lab. You may print out the last page and
submit it to your instructor.

Page 1 of 7
CHEM3011 Experiment 3

Materials
Aluminum dish 24 test tubes
Bunsen burner Test tube rack
6 wooden splints 150 mL beaker

Procedure
Part A: Reactions of Hydrocarbons
1. Prepare a data table (Table 1) to record the observations of each of the 5 tests (A to E)
below. Each test will be conducted on an alkane, alkene, and an aromatic compound.
2. Perform each of the tests below on cyclohexane, cyclohexene and toluene. Compare the
results of each test for the 3 hydrocarbons.

Test 1: Combustion Reactions

1. Make sure that the extractor in the fume hood is switched on.
2. Place an aluminum dish in the fume hood.
3. Add 3-4 drops of cyclohexane to the aluminum dish.
4. Close the bottle of cyclohexane and move it away from the aluminum dish.
5. Light a Bunsen burner in the fume hood.
6. Light a wooden splint with the Bunsen burner.
7. Close the fume hood window so the opening is only 10 cm or less.
8. Light the cyclohexane with the wooden splint.
9. Observe the color of the flame and any smoke or soot (black product) that is produced.
Record these observations in Table 1.
10. Repeat Steps 2 to 9 using cyclohexene.
11. Repeat Steps 2 to 9 using toluene.
12. Turn off the Bunsen burner.

Page 2 of 7
CHEM3011 Experiment 3

Test 2: Reaction with Bromine

Note: Bromine is toxic and corrosive. Wear gloves during this part!
1. In the fume hood, add approximately 2 mL of cyclohexane to a test tube.
2. Close the bottle of cyclohexane.
3. Close the fume hood window so the opening is 30 cm or less.
4. In the test tube, add 5 drops of bromine solution and 5 drops of acetone.
5. Observe any change in color or gas that is produced. Record these observations in Table 1.
6. Repeat Steps 1 to 6 using cyclohexene.
7. Repeat Steps 1 to 6 using toluene.
8. Close the bottle of bromine solution.
9. Dispose of the solutions in the “Halogenated Hydrocarbons” dump.

Test 3: Reaction with Acidified Potassium Permanganate

1. In the fume hood, add 3-4 drops of cyclohexane to a new test tube.
2. Close the bottle of cyclohexane.
3. Add approximately 1 mL of dilute sulfuric acid to the test tube.
4. Gently mix the solution by tapping the bottom of the test tube.
5. Add 5-6 drops of potassium permanganate solution and mix the solution by tapping the
bottom of the test tube.
6. Record the color of the mixture in Table 1.
7. Repeat Steps 1 to 6 using cyclohexene.
8. Repeat Steps 1 to 6 using toluene.
9. Dispose of the solutions in the “Permanganate” dump.

Page 3 of 7
CHEM3011 Experiment 3

Test 4: Reaction with Concentrated Sulfuric Acid

Note: Concentrated sulfuric acid is very corrosive. Wear gloves during this part!
1. In the fume hood, add 1 mL of concentrated sulfuric acid to a new test tube.
2. Add approximately 1 mL of cyclohexane to the test tube.
3. Close the bottle of cyclohexane.
4. Observe the solubility of the two substances. Record all observations in Table 1.
5. Repeat Steps 1 to 4 using cyclohexene.
6. Repeat Steps 1 to 4 using toluene.
7. Dispose of all three mixtures by slowly adding them to a 150 mL beaker filled with
approximately 100 mL of water.
8. Dispose of the mixture in the “Sulfuric Acid” dump.

Part B: Determination of Unknown Hydrocarbons

1. Prepare a second data table (Table 2) to record the observations of each of the 5 tests to be
conducted on each of three (3) unknown hydrocarbon compounds.
2. Obtain 3 unknown liquids from your instructor.
3. Repeat all steps in Test 1 for the three unknowns. Record all observations in Table 2.
4. Repeat all steps in Test 2 for the three unknowns. Record all observations in Table 2.
5. Repeat all steps in Test 3 for the three unknowns. Record all observations in Table 2.
6. Repeat all steps in Test 4 for the three unknowns. Record all observations in Table 2.
7. Complete your report and submit it to the lab instructor.

Page 4 of 7
CHEM3011 Experiment 3

Questions
1. Write a balanced chemical equation for each of the reactions observed for Tests 1-3 in
Table 1.

2. Did the result of the bromine test with cyclohexane give you the expected result? Why
did you not observe a reaction?

3. Alkanes usually resist oxidation with oxidizing agents such as KMnO4, however alkanes
containing a tertiary hydrogen (hence tertiary carbon) can be oxidized.
a. Did Test 3 give you the expected results with cyclohexane?
b. Write a chemical equation for the oxidation reaction of 2-methylbutane with
KMnO4.

4. Why do you think aromatic compounds produce more soot (black powder) than
alkanes?

5. Which test(s) can distinguish between the groupings indicated below?

a. Alkanes and alkenes?
b. Alkanes and aromatics?
c. Alkenes and aromatics?

6. Use the data collected in Table 1 and Table 2 to identify whether each of your three
unknowns is an alkane, alkene, or aromatic hydrocarbon. Justify each of your
selections.

Page 5 of 7
CHEM3011 Experiment 3

References

Page 6 of 7
CHEM3011 Experiment 3

Pre-Lab Assignment 3
Properties of Hydrocarbons

STUDENT NAME Grade:

❑ =¿
6
STUDENT ID

Answer the following questions BEFORE the lab session and submit to your instructor upon
entry into the lab.
1. Write a balanced chemical equation for the complete combustion of cyclobutane.
[2 marks]

2. Write a balanced chemical equation for the reaction of propene with chlorine.
[2 marks]

3. Write a balanced chemical equation for the reaction of cyclopentane with bromine, and
indicate what conditions must exist for the reaction to take place. [2 marks]

Page 7 of 7