Core practical 6 Teacher sheet

EDEXCEL Chemistry Teacher Resource Pack 1 Investigating chlorination of 2-methylpropan-2-ol

Core practical 6: Investigating chlorination of 2-methylpropan-2-ol

Objective
● To produce and purify a sample of 2-chloro-2-methylpropane
Safety Specification links
● Wear goggles and gloves. ● Practical techniques 2, 4, 7, 9,
● 2-methylpropan-2-ol is flammable and harmful. 11
● CPAC 1a, 2a, 2b, 3a, 3b, 3c
● Concentrated hydrochloric acid is corrosive and the
hydrogen chloride fumes it produces are toxic and
corrosive. Carry out this practical in a fume cupboard or
well-ventilated room.
● 2-chloro-2-methylpropane is flammable.
● Calcium chloride is an irritant.
Procedure Notes on procedure
1. Pour 10 cm3 of 2-methylpropan-2-ol and 35 cm3 of ● This practical procedure is
concentrated hydrochloric acid into a large conical probably best carried out over
flask. Swirl the contents of the flask very gently. two lessons with the crude
2. Place the bung in the mouth of the flask. Gently swirl product being left to dry between
again, then remove the bung to release the pressure. lessons.

3. Continue swirling the mixture with the bung fitted and

then releasing the pressure for around 20 minutes.
There should be two layers in the flask. The upper
layer is the crude product.
4. Add approximately 6 g of powdered anhydrous calcium
chloride to the flask and swirl until it has dissolved. This
ensures that any unreacted alcohol is in the lower
aqueous layer.
5. Transfer the reaction mixture to a separating funnel.
Allow the mixture to settle into the two layers. Run off
and discard the lower layer. Retain the upper organic
layer in the separating funnel.
6. Add approximately 20 cm 3 of sodium
hydrogencarbonate solution to the separating funnel.
Swirl the funnel and remove the bung to release the
pressure, caused by the production of carbon dioxide,
at frequent intervals. Run off and discard the lower
aqueous layer.
7. Repeat the washing with sodium hydrogencarbonate,
shake the separating funnel and release the carbon
dioxide gas produced, at frequent intervals.
8. Run off and discard the lower layer. Ensure none of the
aqueous layer remains
in the tap.
9. Run off the organic layer into a small conical flask. Add
a spatula full of anhydrous sodium sulfate. Place the
bung in the flask and swirl the contents to mix. Leave
the mixture until the liquid looks completely clear,
swirling occasionally.
10. Decant the organic liquid into a 50 cm 3 pear-shaped (or
round-bottomed) flask.

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 Core practical 6 Teacher sheet
EDEXCEL Chemistry Teacher Resource Pack 1 Investigating chlorination of 2-methylpropan-2-ol

11. Set the flask up for distillation, as shown in the diagram

below.

12. Collect the fraction boiling between 50 °C and 52 °C.

13. Place your pure product in a labelled sample tube.
Answers to questions
1. (CH3)3COH + HCl → (CH3)3CCl + H2O
2. (unreacted) HCl
HCl + NaHCO3 → NaCl + CO2 + H2O
3. 2-methylpropan-2-ol can form hydrogen bonds, 2-chloro-2-methylpropane cannot.
2-methylpropan-2-ol is able to form hydrogen bonds with water and so it is soluble
in water.
2-chloro-2-methylpropane cannot form hydrogen bonds with water and so is insoluble in water.
Intermolecular hydrogen bonds in 2-methylpropan-2-ol are stronger than the dipole-dipole
attractions and London forces between molecules in 2-chloro-2-methylpropane so more energy
is required to separate the molecules.

Practical activities have been safety checked but not trialled by © Pearson Education Ltd 2015
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 Core practical 6 Student sheet
EDEXCEL Chemistry Teacher Resource Pack 1 Investigating chlorination of 2-methylpropan-2-ol

Core practical 6: Investigating chlorination of 2-methylpropan-2-ol

Objective
● To produce and purify a sample of 2-chloro-2-methylpropane
Safety
● Wear goggles and gloves.
● 2-methylpropan-2-ol is flammable and harmful.
● Concentrated hydrochloric acid is corrosive and the hydrogen chloride fumes it produces are
toxic and corrosive. Carry out this practical in a fume cupboard or well-ventilated room.
● 2-chloro-2-methylpropane is flammable.
● Calcium chloride is an irritant.
All the maths you need
● Use ratios to construct and balance equations.
● Use percentages to calculate percentage yield.
Equipment
● large 250 cm3 conical flask with bung
● 100 cm3 (or larger) separating funnel with bung
● 250 cm3 beaker for liquid run out of separating funnel
● filter funnel to fit separating funnel
● apparatus for distillation with 50 cm 3 pear-shaped (or round-bottomed) flask and thermometer
able to read up to 100 °C
● 25 cm3 and 100 cm3 measuring cylinders
● 2-methylpropan-2-ol
● sodium hydrogencarbonate solution
● 6 g powdered anhydrous calcium chloride
● anhydrous sodium sulfate
● small conical flasks with bungs
● sample tube
● silver nitrate solution
● dilute sodium hydroxide solution
● dilute nitric acid
● 70 cm3 concentrated hydrochloric acid
● test tubes
● spatulas
● 5 cm3 ethanol
● Bunsen burner

Practical activities have been safety checked but not trialled by © Pearson Education Ltd 2015
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This document may have been altered from the original 1
local circumstances.
 Core practical 6 Student sheet
EDEXCEL Chemistry Teacher Resource Pack 1 Investigating chlorination of 2-methylpropan-2-ol

Diagram

Procedure
1. Pour 10 cm3 of 2-methylpropan-2-ol and 35 cm3 of concentrated hydrochloric acid into a large
conical flask. Swirl the contents of the flask very gently.
2. Place the bung in the mouth of the flask. Gently swirl again, then remove the bung to release
the pressure.
3. Continue swirling the mixture with the bung fitted and then releasing the pressure for around 20
minutes. There should be two layers in the flask. The upper layer is the crude product.
4. Add approximately 6 g of powdered anhydrous calcium chloride to the flask and swirl until it has
dissolved. This ensures that any unreacted alcohol is in the lower aqueous layer.
5. Transfer the reaction mixture to a separating funnel. Allow the mixture to settle into the two
layers. Run off and discard the lower layer. Retain the upper organic layer in the separating
funnel.
6. Add approximately 20 cm 3 of sodium hydrogencarbonate solution to the separating funnel.
Swirl the funnel and remove the bung to release the pressure, caused by the production of
carbon dioxide, at frequent intervals. Run off and discard the lower aqueous layer.
7. Repeat the washing with sodium hydrogencarbonate, shake the separating funnel and release
the carbon dioxide gas produced, at frequent intervals.
8. Run off and discard the lower layer. Ensure none of the aqueous layer remains
in the tap.
9. Run off the organic layer into a small conical flask. Add a spatula full of anhydrous sodium
sulfate. Place the bung in the flask and swirl the contents to mix. Leave the mixture until the
liquid looks completely clear, swirling occasionally.
10. Decant the organic liquid into a 50 cm 3 pear-shaped (or round-bottomed) flask.
11. Set the flask up for distillation, as shown in the diagram above.
12. Collect the fraction boiling between 50 °C and 52 °C.
13. Place your pure product into a labelled sample tube.

Practical activities have been safety checked but not trialled by © Pearson Education Ltd 2015
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local circumstances.
 Core practical 6 Student sheet
EDEXCEL Chemistry Teacher Resource Pack 1 Investigating chlorination of 2-methylpropan-2-ol

Analysis of results
Perform the following test on the distillate:
● Place a few drops of the distillate into a test tube. Add 5 cm3 of ethanol and 1 cm 3 of aqueous
sodium hydroxide to the test tube. Warm the mixture in a water bath. Add excess nitric acid to
the mixture followed by a few drops of silver nitrate solution.
Learning tips
● The –OH group in an alcohol can be replaced by a halogen. PCl5 can be used to make a
chloroalkane, HBr (which is made in situ) can be used to make a bromoalkane, and red
phosphorus with iodine can be used to make an iodoalkane.
● The purity of a substance can be checked by measuring its boiling temperature.
Questions
1. Write an equation for the reaction of 2-methylpropan-2-ol with concentrated hydrochloric acid.
2. What is removed from the crude product when it is shaken with sodium hydrogencarbonate
solution? Write an equation for any reaction that occurs.
3. 2-methylpropan-2-ol has a boiling temperature of 82 °C and is soluble in water.
2-chloro-2-methylpropane has a boiling temperature of 51 °C and is insoluble in water. Explain
these differences.

Practical activities have been safety checked but not trialled by © Pearson Education Ltd 2015
CLEAPSS. Users may need to adapt the risk assessment information to
This document may have been altered from the original 3
local circumstances.
 Core practical 6 Technician sheet
EDEXCEL Chemistry Teacher Resource Pack 1 Investigating chlorination of 2-methylpropan-2-ol

Core practical 6: Investigating chlorination of 2-methylpropan-2-ol

Objective
● To produce and purify a sample of 2-chloro-2-methylpropane
Safety
● Wear eye protection.
● 2-methylpropan-2-ol is flammable and harmful.
● Concentrated hydrochloric acid is corrosive and the hydrogen chloride fumes it produces are
toxic and corrosive.
● 2-chloro-2-methylpropane is flammable.
● Calcium chloride is an irritant.
Equipment per student/group Notes on equipment
large 250 cm3 conical flask with bung
100 cm3 (or larger) separating funnel with bung
250 cm3 beaker for liquid run out of separating
funnel
filter funnel to fit separating funnel
apparatus for distillation with 50 cm 3 pear-shaped
(or round-bottomed) flask and thermometer able to
read up to 100 °C
25 cm3 and 100 cm3 measuring cylinders
2-methylpropan-2-ol 10 cm3 per student
concentrated hydrochloric acid 35 cm3 per student
sodium hydrogencarbonate solution 0.1 mol dm–3
powdered anhydrous calcium chloride 6 g per student
anhydrous sodium sulfate 1 g
small conical flasks with bungs No bigger than 100 cm3
test tubes
sample tube
silver nitrate solution Normal concentration of ion tests
dilute sodium hydroxide solution
dilute nitric acid
spatulas
ethanol 5 cm3 per student
Bunsen burner
kettle To prepare the water bath

Notes

Practical activities have been safety checked but not trialled by © Pearson Education Ltd 2015
CLEAPSS. Users may need to adapt the risk assessment information to
This document may have been altered from the original 1
local circumstances.