Test for unsaturation

Background: When alkanes are shaken with aqueous bromine, a substitution reaction occurs
in which a colourless oily bromoalkane and hydrogen bromide are formed. This reaction is
very slow in the dark but speeds up in the presence of sunlight.

An addition reaction occurs between an alkene and bromine, the only product of the reaction
being a dibromoalkane. This reaction needs no sunlight or other form of radiation to go to
completion.

A student carrying out the reaction between cyclohexane and aqueous bromine reported: ‘The
cyclohexane is not miscible with the lower aqueous layer which initially contains the
bromine. Initially, the upper layer is colourless whereas the lower layer is orange coloured.
But the bromine is more soluble in the organic layer and moves into it when the mixture is
shaken. The colour of the lower layer begins to lighten as the substitution reaction occurs.’

Plan and design a lab to investigate the reactions of alkanes and alkenes.

Syllabus Topic: Organic Chemistry

Title: Comparing the reactions of a saturated (alkane) and unsaturated (alkene) carbon
compound with bromine.
Hypothesis: The alkene compound would be more reactive than the alkane compound.

Aim: To investigate the reactions of alkanes and alkenes with aqueous bromine and
potassium permanganate (VII).

Apparatus and Material: test tubes, test tube rack, droppers, cyclohexane, cyclohexene,
aqueous bromine, potassium permanganate (VII).

Method:

1) Set aside 4 test tubes and label each in the order A, B, C, and D.

2) Assign a designated dropper for each solution to be used in the experiment.

3) In test tube A, using the designated dropper, add 1 ml of cyclohexane and 1 ml of

aqueous bromine solution. Stir the solution and record any observations made.

4) In test tube B, using the designated dropper, add 1 ml of cyclohexane and 1 ml of

potassium permanganate (VII). Stir the solution and record any observations made.

5) In test tube C, using the designated dropper, add 1 ml of cyclohexene and 1 ml of

aqueous bromine solution. Stir the solution and record any observations made.

6) In test tube D, using the designated dropper, add 1 ml of cyclohexene and 1 ml of

potassium permanganate (VII). Stir the solution and record any observations made.

Variables:

Controlled:

1) Volume of each solution used in the experiment.

2) Concentration of aqueous bromine solution.

Manipulated:

1) The aqueous bromine solution and potassium permanganate (VII).

Responding:

1) Colour changes observed in the experiment.

Data to be collected/Results::

Results:
TITLE: Table 1 ________________________________

Test 1 with Test 2 with

aqueous bromine Potassium
solution. permanganate
(VII)

Alkane

Alkene

Statement of predicted results:

No reaction will occur between cyclohexane, aqueous bromine, and potassium permanganate
(VII). Therefore, the saturated compound will be less reactive than the unsaturated
compound. If the results do not support the hypothesis, the hypothesis will be false.

Precautions:

1) All protective equipment such as gloves and lab coats are to be worn during the
experiment.
2) Different droppers should be used for each solution to prevent contamination.

Limitations:

1) Bromine is volatile.