Alkenes and Alkanes

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Name: _______________________

First hand Investigation: Alkenes V Alkanes


Dot Point 9.2.1.2.2

Identify data, plan and perform a first- hand investigation to compare the reactivity of appropriate alkenes
with the corresponding alkanes in bromine water

Aim: To compare the reactivity of an alkene and its corresponding alkane in bromine water (aqueous
bromine) and describe the chemistry involved.

Background Information

Cyclohexane and cyclohexene are both colourless, volatile liquids at room temperature, and are therefore
suitable to be used in this experiment as long as they are handled properly. Ethane and ethene are both gases
under laboratory conditions and are therefore not suitable to be used in this experiment.

Reaction with bromine is often used in the laboratory to distinguish between alkenes and alkanes.

Bromine can either be dissolved in a non-aqueous solvent, such chloroform, or in an aqueous solution called
bromine water. Bromine water is favoured in school laboratories as it is safer to use.

In either case, drops of bromine solution are added to the colourless sample to be tested and shaken gently.
If the sample decolourises the bromine solution, the sample is an alkene; if the sample takes on the brown
colour of the bromine (but does not react with the bromine) it is an alkane.

In the case of bromine water, the bromine is dissolved in water to form an equilibrium mixture of
hypobromous acid.

Br2 + H2O  H+ + Br- + HOBr


Shaking bromine water with an unsaturated hydrocarbon will rapidly decolourise the bromine water. The
hydrocarbon reacts with the hypobromous acid (HOBr). As this occurs more Br2 reacts with water and so its
colour fades.

Risk Assessment

Cyclohexane, cyclohexene and bromine water are toxic substances with unpleasant odours. In order to
minimise the risks, the following procedures should be followed:

 Small quantities only should be used


 Stock solutions should be in dropper or stoppered bottles
 Transfer of chemicals and observation should occur inside a working fume cupboard
 Waste materials should be placed in the halogenated hydrocarbons bottle (also located in the fume
cupboard).
 Aprons and safety glasses should be worn by all students
Complete the following before beginning the experiment

1. Write the molecular formula for:

(a) cyclohexane

(b) cyclohexene

(c) bromine

2. Draw the structural formula for:

(a) cyclohexane

(b) cyclohexene

(c) a bromine molecule


3. Classify cyclohexane, cyclohexene and bromine as polar or non- polar substances.

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4. Comment on their expected solubility in water.

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5. Bromine water (aqueous bromine) contains bromine molecules dissolved (at about 2.8%) in water.
Explain why this is referred to as partial solubility.

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Procedure

 Place 2 medium test tubes in a test tube rack and proceed to the fume cupboard.
 Add 1 mL of cyclohexane to one test tube and 1 mL of cyclohexene to the other.
 Add 1 mL of bromine water to each test tube.
 Observe each test tube before and after gentle shaking.
 Record your observations.

Observations

The test tube containing the cyclohexane and bromine water:


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The test tube containing the cyclohexene and bromine water:


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Explain the chemistry relating to your observations

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Write the equation (using structural formula) that shows the reaction between the cyclohexene and the
bromine water. NB; The reaction between Bromine and H2O in bromine water is an equilibrium reaction.
This means bromine water contains Br2, H2O, H+, Br- and HOBr at all times. Hypobromous acid has a far
greater affinity for Cyclohexene than B2 so while both are capable of reacting with the alkene, the reaction
with HOBr predominates.

Write the equation (using structural formula) that shows the reaction that would have occurred had a non-
aqueous solution of bromine been used instead of bromine water.

Write the word equations for the above 2 reactions.

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Analysis & Discussion
Was a catalyst used in this reaction? Explain.

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What type of chemical reaction did the cyclohexene undergo?

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An extension of this investigation involves exposing the test tube containing the cyclohexane and bromine
water to sunlight.

What would you expect to observe?

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What type of chemical reaction would be taking place?

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Explain the chemistry behind this reaction.

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Write the structural and word equations that describe this reaction.

SE

WE

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Name the carbon based compound that would be formed if this reaction continued to completion.

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Write a suitable Conclusion for this experiment.

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