Unit 14: Applications of Organic Chemistry
Learning aim D: investigate organic chemistry reactions in order to gain skills in preparative organic
chemistry
Assignment title: Making Designer Chemicals
Preparation of a compound without a carbonyl functional group (e.g. an alcohol from a
halogenoalkane, a halogenoalkane from an alcohol)
Investigating chlorination of 2-methylpropan-2-ol
Objectives:
To produce and purify a sample of 2-chloro-2-methylpropane
Health and safety
Make sure to wear safety goggles, a lab coat, and gloves
2-methylpropan-2-ol is a flammable and harmful substance
2-chloro-2-methylpropane can easily catch fire
Calcium chloride is an irritant chemical
Concentrated hydrochloric acid is corrosive and the hydrogen chloride fumes it produces are toxic and
corrosive.
Equipment
Large 250cm3 conical flask with bung
100cm3 separating funnel with bung
250cm3 beaker for liquid run out of separating funnel
Filter funnel to fit separating funnel
Apparatus for distillation with 50cm3 pear-shaped (or round-bottomed) flask and thermometer
able to read up to 100 C
25cm3 and 100cm3 measuring cylinders
2-methylpropan-2-ol
Sodium hydrogen carbonate solution
6g 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
5cm3 ethanol
, Bunsen burner
Method
1. In a large conical flask, combine 10cm3 2-methylpropan-2-ol and 35cm3 concentrated
hydrochloric acid. Gently swirl the contents in the flask.
2. Place the bung in the flask's mouth. Remove the bung and gently spin once more to release the
pressure.
3. Continue spinning the liquid with the bung in place for about 20 minutes before releasing the
pressure. In the flask, there should be two layers. The crude product is on the top layer.
4. Swirl around 6 grammes of powdered anhydrous calcium chloride into the flask until it dissolves.
This keeps any unreacted alcohol in the watery layer below.
5. Fill a separating funnel halfway with the reaction mixture. Allow two layers to form in the
mixture. Remove the lower layer and discard it. Keep the organic layer on top in the separating
funnel.
6. In the separating funnel, pour around 20cm3 of sodium hydrogen carbonate solution. Swirl the
funnel and remove the bung at regular intervals to relieve the pressure created by the carbon
dioxide production. The lowest watery layer should be run off and discarded.
7. At regular intervals, repeat the washing with sodium hydrogen carbonate, shake the separating
funnel, and release the carbon dioxide gas created.
8. Remove the lower layer and discard it. Make sure the aqueous layer is not left in the tap.
9. Using a tiny conical flask, drain the organic layer. A spatula full of anhydrous sodium sulphate
should be added. Swirl the contents of the flask with the bung to combine them. Allow the
mixture to sit until it seems fully clear, swirling it occasionally.
10. Fill a 50 cm3 pear-shaped (or round-bottomed) flask halfway with organic liquid.
11. As shown in the diagram, set up the flask for distillation.
12. Collect the portion that is boiling between 50 and 52 degrees Celsius.
13. Fill a sample tube with your pure product and label it.
Learning aim D: investigate organic chemistry reactions in order to gain skills in preparative organic
chemistry
Assignment title: Making Designer Chemicals
Preparation of a compound without a carbonyl functional group (e.g. an alcohol from a
halogenoalkane, a halogenoalkane from an alcohol)
Investigating chlorination of 2-methylpropan-2-ol
Objectives:
To produce and purify a sample of 2-chloro-2-methylpropane
Health and safety
Make sure to wear safety goggles, a lab coat, and gloves
2-methylpropan-2-ol is a flammable and harmful substance
2-chloro-2-methylpropane can easily catch fire
Calcium chloride is an irritant chemical
Concentrated hydrochloric acid is corrosive and the hydrogen chloride fumes it produces are toxic and
corrosive.
Equipment
Large 250cm3 conical flask with bung
100cm3 separating funnel with bung
250cm3 beaker for liquid run out of separating funnel
Filter funnel to fit separating funnel
Apparatus for distillation with 50cm3 pear-shaped (or round-bottomed) flask and thermometer
able to read up to 100 C
25cm3 and 100cm3 measuring cylinders
2-methylpropan-2-ol
Sodium hydrogen carbonate solution
6g 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
5cm3 ethanol
, Bunsen burner
Method
1. In a large conical flask, combine 10cm3 2-methylpropan-2-ol and 35cm3 concentrated
hydrochloric acid. Gently swirl the contents in the flask.
2. Place the bung in the flask's mouth. Remove the bung and gently spin once more to release the
pressure.
3. Continue spinning the liquid with the bung in place for about 20 minutes before releasing the
pressure. In the flask, there should be two layers. The crude product is on the top layer.
4. Swirl around 6 grammes of powdered anhydrous calcium chloride into the flask until it dissolves.
This keeps any unreacted alcohol in the watery layer below.
5. Fill a separating funnel halfway with the reaction mixture. Allow two layers to form in the
mixture. Remove the lower layer and discard it. Keep the organic layer on top in the separating
funnel.
6. In the separating funnel, pour around 20cm3 of sodium hydrogen carbonate solution. Swirl the
funnel and remove the bung at regular intervals to relieve the pressure created by the carbon
dioxide production. The lowest watery layer should be run off and discarded.
7. At regular intervals, repeat the washing with sodium hydrogen carbonate, shake the separating
funnel, and release the carbon dioxide gas created.
8. Remove the lower layer and discard it. Make sure the aqueous layer is not left in the tap.
9. Using a tiny conical flask, drain the organic layer. A spatula full of anhydrous sodium sulphate
should be added. Swirl the contents of the flask with the bung to combine them. Allow the
mixture to sit until it seems fully clear, swirling it occasionally.
10. Fill a 50 cm3 pear-shaped (or round-bottomed) flask halfway with organic liquid.
11. As shown in the diagram, set up the flask for distillation.
12. Collect the portion that is boiling between 50 and 52 degrees Celsius.
13. Fill a sample tube with your pure product and label it.
