EXPERIMENT #3: REACTIONS OF HYDROCARBONS

The reactions of saturated hydrocarbons are different from that of unsaturated

ones. Generally, unsaturated hydrocarbons are more reactive than saturated
hydrocarbons. Addition of strong oxidative reagent like Bayer’s reagent (basic potassium
permanganate) leads to the formation of alcohol for alkenes and carboxylic acids for
alkynes. Tollen’s reagent is a weak oxidizing agent composed of ammoniacal silver
nitrate. It reacts with terminal alkynes to form silver alkylides. Halogenation is the
addition of halide substituents like bromine. This occurs via different mechanisms and
extent with different hydrocarbons.

Objectives
In this experiment, you will be able to distinguish hydrocarbons based on their
characteristic reactions. Using this knowledge, you will understand how to identify
unknown hydrocarbon samples. Lastly, you will be able to generate acetylene, an
economically useful alkyne, from a simple reaction.

Materials and Reagent

Hexane Bromine in CCl4 Screw-
capped test tubes
D-Limonene Bayer’s reagent Separatory funnel
Calcium carbide Distilled water Distilling
flask
Unknown hydrocarbon 1 Tollen’s reagent Iron ring and clamp
Unknown hydrocarbon 2 Pasteur pipettes Rubber tubing and
pinchcock

Procedures

PRECAUTIONS: Hydrocarbons are combustible compound. Generation of acetylene is a

highly exothermic process. Avoid direct skin contact and inhalation of vapour of
hydrocarbons. Tollen’s reagent has an explosive tendency when it forms alkylide
precipitates. Dilute with copious amount of water and dispose of it immediately!

1. Place 5 drops of hexane, D-limonene, unknown hydrocarbon 1, and unknown

hydrocarbon 2 on separate dry test tubes. Prepare new set of samples for each of
the chemical test below:
a. Bayer’s test – add 5 drops of Bayer’s reagent to each sample. Shake and then
observe.
b. Bromination (with light) – add 5 drops of bromine. Shake and then observe.
c. Bromination (without light) – wrap the test tube with paper, add 5 drops of
bromine and immediately place the sample in a dark place for 2 minutes.
Observe afterwards.
d. Tollen’s test – add 5 drops of Tollen’s reagent. Shake and then observe.

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2. Prepare the set-up for acetylene generation as in Figure 1 [one set-up will suffice for
the whole class]. Add the chemicals as listed in #1 a-d to four separate dry screw-
capped test tubes [one for each group].
3. Add small increments of water to calcium carbide at a time to initiate the formation
of acetylene. Collect acetylene into the test tubes by inserting the end of the rubber
tubing and then opening the pinchcock. When enough acetylene is collected, cap
the tubes immediately and observe any ensuing reaction.
4. From the results of the tests, identify whether your unknown sample is an alkane,
alkene, or alkyne.
5. Write the pertinent general equations involved in each reaction.

Figure 1. Acetylene Generation Set-up

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 DATA SHEET

NAME:________________________________________________________________
SCORE:_________

SECTION:______ DATE PERFORMED:____________

INSTRUCTOR:_____________________________

A. Chemical Test Results (20pts)

Bayer’s Br2 Test Br2 Test Tollen’s

Test (light) (dark) Test
Visible +
result
SAMPLES
Hexane
D-Limonene
Acetylene
Unknown 1
Unknown 2
Legend: ++  fast reaction; +  slow reaction; -  no reaction

Identities of Unknown Hydrocarbons

Sample 1:___________________________
Sample 2:___________________________

B. Pertinent General Reactions (15 pts)

(1) Bayer’s oxidation:

(2) Bromination (light):

(3) Bromination (dark):

(4) Tollen’s Test:

C. Follow-up Questions and Applications (15 pts)

1. Which of the above chemical tests can be used to distinguish the following? (3 pts)
a. Alkane from alkene

b. Alkane from alkyne

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c. Alkene from alkyne

2. Why are unsaturated hydrocarbons more reactive than saturated ones? (3 pts)
3. What is the difference between the mechanism of bromination of saturated and
unsaturated hydrocarbons? (3pts)
4. What is the chemical equation involved in the generation of acetylene? (3 pts)
5. What are the economic uses of acetylene? (3pts)