Biochemistry for Allied Medical Courses 35

Laboratory Manual

Laboratory Procedure Activity

Hydrocarbons: 7
Structure and Properties

INTRODUCTION

The term “hydrocarbons” refers to those organic compounds which contain only carbon
and hydrogen. On the basis of structure, hydrocarbons are divided into two main
classes, aliphatic and aromatic. Aliphatic hydrocarbons are further divided into two
groups: saturated hydrocarbons and unsaturated hydrocarbons. Saturated hydrocarbons
include alkanes and the cyclic aliphatic which are characterized by the presence of only
sigma bonds (), hence the carbon atoms are all single-bonded. Unsaturated
hydrocarbons include the alkenes and the alkynes which have pi bonds. The presence of
pi bonds in unsaturated hydrocarbons is due to less number of hydrogen atoms
compared to the saturated counterparts. The carbon-carbon double bond (C=C) in
alkenes or triple bond (CC) in alkynes is therefore the distinguishing feature of
unsaturated hydrocarbons.

Saturated hydrocarbons or alkanes are inert towards HCl and H2SO4 as well as towards
oxidizing agents like KMnO4 and Na2Cr2O7 at room temperature. This inertness can be
attributed to the type of bonds involved in the molecule. In general, alkanes and other
saturated hydrocarbons react towards some reagents by substitution reaction under
rigorous conditions.

On the other hand, the characteristic reactions of an alkene are those that take place at
the double bond. The double bond (C=C) consists of a strong sigma bond and a weak
pi-bond (); one might expect, therefore that reaction would involve in the breaking of
the weak pi bond. The typical reaction of the double bond is indicated in the following
equation:

+ YZ
Y Z
alkene

This is addition reaction, where the pi bond is broken and sigma bonds are formed.

In the laboratory, unsaturation may be detected by using Bromine and CCl4. The
reaction is:
CCl4
+ Br2
Br Br
alkene orange or red colorless

Natural Sciences Department, College of Science and Information Technology, Ateneo de Zamboanga
University, Zamboanga City, Philippines.
Biochemistry for Allied Medical Courses 36
Laboratory Manual

Baeyer’s test is another method of detecting unsaturation. Alkenes can decolorize a cold
dilute, neutral permanganate solution by which the purple color disappears and is
replaced by brown MnO2. This reaction is also exhibited by alkynes (CC).

- CCl4
+ MnO 4 MnO 2 +
HO OH
alkene brown
orange or red colorless
precipitate

Aromatic compounds contain pi bonds in conjugation. Because of the special

arrangement of pi bonds, they exhibit resonance that results to conjugative stability of
the molecule. In reaction, aromatic compounds such as benzene undergo chiefly
substitution reaction, resembling more the saturated hydrocarbons than the unsaturated
hydrocarbons. They 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.

APPARATUS/MATERIALS CHEMICALS/REAGENTS

watch glass benzene

evaporating dish cyclohexane
medicine dropper gasoline
test tubes kerosene
test tube holder n-hexane
graduated cylinder conc. H2SO4
small corks 0.1% KMnO4
medicine dropper 1% NaOH
graduated cylinder 5% solution of bromine in CCl4
medicine droppers naphthalene
anthracene
anhydrous AlCl3
dry chloroform

PROCEDURE

CAUTION: Wear safety goggles, rubber gloves and double-lined mask

! at all times during this activity.

Natural Sciences Department, College of Science and Information Technology, Ateneo de Zamboanga
University, Zamboanga City, Philippines.
Biochemistry for Allied Medical Courses 37
Laboratory Manual

1. Ignition Test

a. Place 1 drop of benzene in a dry watch glass. Ignite it with a lighted

match stick. 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: (1) n-hexane, (2) cyclohexane, (3) kerosene and
(4) gasoline, in place of benzene. Record your observations.

2. Reaction with Concentrated Sulfuric Acid

a. Transfer 2 mL of concentrated sulfuric acid in a dry test tube and add 1

mL of benzene. Shake it vigorously and let it stand for a few minutes.
Note if a single phase is formed.
b. Repeat the test with: (1) n-hexane, (2) cyclohexane, (3) kerosene and
(4) gasoline, in place of benzene.

3. Baeyer’s Test for Unsaturation

a. Render 5 mL of 0.1% KMnO4 solution alkaline by adding 1% NaOH drop

by drop until it gives a positive test with red litmus paper. Set aside 1 mL
of the prepared solution as standard. Use the rest as reagent.
b. In 5 separate dry test tubes, place 10 drops of the ff: benzene, n-hexane,
cyclohexane, kerosene, and gasoline. Then add 15 drops of the alkaline
KMnO4 on each test tube. Compare the color with the standard.

IMPORTANT: Avoid strong light and heat. Record the results

 immediately.

4. Bromine in Carbon Tetrachloride Test

a. Prepare 5 mL of 5% solution of bromine in CCl4. Set aside 1 mL of the

prepared solution as standard. Use the rest as reagent.

! CAUTION: Bromine gas is toxic. Cover all containers tightly. Perform

this test in the HOOD.

b. In 5 separate test tubes place 10 drops of the ff: benzene, n-hexane,

cyclohexane, kerosene, and gasoline. Then add 15 drops of the bromine

Natural Sciences Department, College of Science and Information Technology, Ateneo de Zamboanga
University, Zamboanga City, Philippines.
Biochemistry for Allied Medical Courses 38
Laboratory Manual

in CCl4 reagent to each test tube. Observe and compare the color with
the standard.

IMPORTANT: Avoid strong light and heat. Record the results

 immediately.

5. Test for Aromatic Hydrocarbons

a. Heat 0.1 g of anhydrous AlCl3 in a dry Pyrex test tube until the AlCl3 has
sublimed. Cool.
b. Add 1 drop of benzene by allowing it to flow on the side of the test tube.
Do the same with 2 to 3 drops of dry chloroform. Observe the color
produced at the point of contact.
c. Repeat the test using a pinch of (1) naphthalene and (2) anthracene in
place of benzene.

QUESTIONS

1. How can methane, ethylene and acetylene be prepared in the laboratory? Write
the chemical reactions involved in such preparations.
2. What type of reaction is exhibited by alkenes? Why?
3. Explain the reaction of benzene with anhydrous AlCl3 and chloroform.
4. Account for the reactivity of gasoline.
5. Hydrocarbons comprise a majority of fossil fuels. What are the environmental
implications of this activity?

Natural Sciences Department, College of Science and Information Technology, Ateneo de Zamboanga
University, Zamboanga City, Philippines.
Biochemistry for Allied Medical Courses 39
Laboratory Manual

Group No.___ Date Performed :___________

Subject & Section: ________ Facilitator’s Initials :___________
Members:
1. _____________________
2. _____________________
3. _____________________

Data Sheet Activity

Hydrocarbons: 7
Structure and Properties

Data

Observations:

1. Ignition Test

benzene n-hexane cyclohexane kerosene gasoline

2. Reaction with Concentrated Sulfuric Acid

benzene n-hexane cyclohexane kerosene gasoline

3. Baeyer’s Test for Unsaturation

Color of standard solution: _________________________________

benzene n-hexane cyclohexane kerosene gasoline

Natural Sciences Department, College of Science and Information Technology, Ateneo de Zamboanga
University, Zamboanga City, Philippines.
Biochemistry for Allied Medical Courses 40
Laboratory Manual

4. Bromine in Carbon Tetrachloride Test

Color of standard solution: _________________________________

benzene n-hexane cyclohexane kerosene gasoline

5. Test for Aromatic Hydrocarbons

benzene chloroform naphthalene anthracene

Natural Sciences Department, College of Science and Information Technology, Ateneo de Zamboanga
University, Zamboanga City, Philippines.