Experiment 7 - Hydrocarbons

INORGANIC AND ORGANIC CHEMISTRY LABORATORY
UNIVERSITY OF LA SALETTE, INC.

Santiago City, Philippines
COLLEGE OF MEDICINE AND ALLIED MEDICAL PROGRAMS
Medical Laboratory Science Department
LABORATORY ACTIVITY NO. 7:

HYDROCARBONS—STRUCTURES AND CHEMICAL PROPERTIES
OBJECTIVES:
• To observe the properties of samples of hydrocarbons and relate them with their
classification and structures
PRE-LABORATORY DISCUSSION:
The term hydrocarbons refer to those organic compounds, which contain only carbon
and hydrogen.
Classification of Hydrocarbons
A. Based on structure
1. Open-chain or Aliphatic Hydrocarbons
2. Closed-chain or Cyclic Hydrocarbons
B. Based on the number of bonds present
1. Saturated Hydrocarbons
‒ characterized by the presence of only sigma bonds
‒ carbon atoms are all SINGE BONDS
‒ include alkanes and the cycloalkanes
‒ generally inert towards HCl and H2SO4 as well as oxidizing agents like
KMnO4 and Na2Cr2O7 at room temperature
‒ Rationale: This inertness can be attributed to the relative strength
of the bonds in the molecule.
‒ in general, alkanes and other saturated hydrocarbons react by
substitution under rigorous conditions
2. Unsaturated Hydrocarbons
‒ characterized by the presence of pi bonds
‒ carbon—carbon double bonds and/or triple bonds are the
distinguishing feature of unsaturated compounds

HYDROCARBONS—STRUCTURES AND CHEMICAL 1
PROPERTIES
Chemical Reactions involving Unsaturated Hydrocarbons
The characteristic reactions of unsaturated hydrocarbons are those that take place at the
double bond. It is therefore expected that the reaction would involve the breaking of the weak
pi bond. The typical reaction of the double bond is indicated in the following equation:
1. Halogenation of Alkenes
‒ Addition of halogen to alkenes
‒ Addition reaction where the pi bond is broken and converted to sigma
bond
‒ Addition of Br2 acts as a simple and rapid laboratory test for
unsaturation.
‒ A sample of unknown structure is dissolved in dichloromethane,
CH2Cl2 (or in other case, CCl4 is used) and several drops of Br2
are added.
‒ Positive result: immediate disappearance of the reddish Br2 color
2. Baeyer’s Test
‒ Alkenes and alkynes can decolorize cold dilute, neutral permanganate
solutions.
‒ Positive results:
‒ Purple color of KMnO4 disappears
‒ Brown color of MnO2 is produced

PROPERTIES
Aromatic Compounds
‒ contain pi bonds in conjugation
‒ exhibit resonance that results in conjugative stability of the molecule
‒ chemical reaction: ELECTROPHILIC AROMATIC SUBSTITUTION
‒ resist addition to the pi bonds in which the ring system would be destroyed, but readily
undergo substitution in which the ring system is preserved
MATERIALS AND REAGENTS:
TEST SAMPLES APPARATUS/MATERIALS REAGENTS

naphthalene watch glass KMnO4
n-hexane evaporating dish 1% NaOH
cyclohexane medicine droppers Bromine in acetic acid solution
gasoline test tubes
benzene small corks
acetanilide test tube holder
1-mL pipette
PROCEDURE:
1. IGNITION TEST
a. Place 1 drop of benzene in a dry watch glass. Ignite it with a lighted matchstick.
Observe whether the flame is luminous or non-luminous.
b. Place a dry evaporating dish over the flame. Note if soot is formed at the bottom
of the evaporating dish.
c. Repeat the test with:
‒ n-hexane
‒ cyclohexane
‒ gasoline, in place of benzene
d. Record your observations.
2. BAEYER’S TEST FOR UNSATURATION

a. Add 1 drop of 1% NaOH to 5 mL of 0.1% KMnO4 to make the solution alkaline.
Set aside 1 mL of the prepared solution as standard. Use the rest as reagent.
b. Place 10 drops of each of the following: benzene, n-hexane, cyclohexane, and
gasoline in 4 separate dry test tubes. Keep in the test tube rack.

PROPERTIES
c. Perform this in the hood: Add 15 drops of the alkaline KMnO4 to each test tube.
Compare the color formed in each test tube with the standard. Avoid strong heat
and light. Present the results immediately to your instructor.
3. ELECTROPHILIC AROMATIC SUBSTITUTION

NOTE: Perform this part in the hood.
a. Dissolve 0.67 g of acetanilide in 2.5 mL of glacial acetic acid in a big test tube.
b. Add drop by drop, with stirring, 0.76 mL (approximately 15 drops) of bromine in
acetic acid solution.
c. Stir the solution for 3 minutes more and add distilled water slowly with stirring
until the solution turns cloudy or a precipitate is formed.
d. Repeat Step A – C using naphthalene instead of acetanilide.

PROPERTIES
POST-LABORATORY DATA SHEET: RESULTS AND OBSERVATIONS
NAME OF TEST COMPOUND REAGENTS OBSERVATION

IGNITION TEST
Benzene
n-hexane
Cyclohexane
Gasoline
BAEYER’S TEST
Benzene
n-hexane
Cyclohexane
Gasoline
ELECTROPHILIC AROMATIC SUBSTITUTION

Acetanilide
Naphthalene

PROPERTIES
POST-LABORATORY QUESTIONS
• Answer the following questions.
• Indicate the references with proper APA format.
1. IGNITION TEST
a. How do the reactions in the ignition test of the hydrocarbon samples of
compare?
b. What is your conclusion regarding the type of combustion each undergoes?
2. BAEYER’S TEST
a. How do you account for the observed reactions of the test compounds in
Baeyer’s Test?
b. What generalization can you give regarding their unsaturation?
3. ELECTROPHILIC AROMATIC SUBSTITUTION

a. What is indicated by the result obtained in the reaction of acetanilide with
bromine in acetic acid?
b. What is indicated by the result obtained in the reaction of naphthalene with

bromine in acetic acid?

PROPERTIES
c. What compounds are the expected products of the reactions in 3A and in 3B,
respectively?
4. Explain what happens to a compound that undergoes electrophilic aromatic

substitution.

PROPERTIES

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INORGANIC AND ORGANIC CHEMISTRY LABORATORY

UNIVERSITY OF LA SALETTE, INC.

LABORATORY ACTIVITY NO. 7:

LABORATORY ACTIVITY NO. 7:

Chemical Reactions involving Unsaturated Hydrocarbons

LABORATORY ACTIVITY NO. 7:

MATERIALS AND REAGENTS:

TEST SAMPLES APPARATUS/MATERIALS REAGENTS

2. BAEYER’S TEST FOR UNSATURATION

LABORATORY ACTIVITY NO. 7:

3. ELECTROPHILIC AROMATIC SUBSTITUTION

LABORATORY ACTIVITY NO. 7:

POST-LABORATORY DATA SHEET: RESULTS AND OBSERVATIONS

NAME OF TEST COMPOUND REAGENTS OBSERVATION

ELECTROPHILIC AROMATIC SUBSTITUTION

LABORATORY ACTIVITY NO. 7:

b. What is your conclusion regarding the type of combustion each undergoes?

b. What generalization can you give regarding their unsaturation?

3. ELECTROPHILIC AROMATIC SUBSTITUTION

b. What is indicated by the result obtained in the reaction of naphthalene with

LABORATORY ACTIVITY NO. 7:

4. Explain what happens to a compound that undergoes electrophilic aromatic

LABORATORY ACTIVITY NO. 7:

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