PRACTICAL ACTIVITIES

10.1

PRACTICAL
ACTIVITIES

PREPARATION OF AN ESTER
Aim

1. Select the alkanol and acid from the following

tabulated information. Measure out the required
volumes using clean measuring cylinders.
Experiment

Alkanoic acid

Alkanol

acetic acid
(24 mL)

ethanol (8 mL)

acetic acid
(24 mL)

propan-1-ol (8 mL)

acetic acid
(24 mL)

butan-1-ol (18 mL)

acetic acid
(24 mL)

pentan-1-ol (10 mL)

butanoic acid
(24 mL)

ethanol (8 mL)

To prepare an ester using the reflux technique

Materials
alkanoic acid (choose either glacial acetic acid or
butanoic acid)
alkanol (choose one from ethanol, propan-1-ol,
butan-1-ol or pentan1-1-ol)
concentrated sulfuric acid (dropper bottle)
(teacher use only)
Quickfit round-bottom boiling flask (100 mL or
250 mL)
reflux condenser with hoses
water bath and Bunsen burner or electric heating
mantle
retort stand, boss heads and clamps
boiling chips
stirring rod
beaker
measuring cylinder
Pasteur pipette

Safety
Wear safety glasses throughout this experiment.
Sulfuric acid is corrosive. Clean up spills
immediately. If the acid is spilled on the skin
then wash the area with large quantities of water.
Seek assistance.
Organic chemicals are flammable. Do not allow
liquids or vapours to come into contact with
sparks or flames.
Identify other safety precautions relevant to this
experiment by reading the method.

Method
Preparation of the ester
Refer to Figure 10.11 in the text to help you set up
the apparatus.

2. Pour the acid and the alkanol into the dry

round-bottom flask. Your teacher will then add
2 mL (40 drops) of concentrated sulfuric acid to
the flask. Now add 2 or 3 boiling chips.
3. Set up the flask and condenser for reflux as
shown. Use a heating mantle, hotplate, Bunsen
burner (with gauze) or hot-water bath to supply
the heat once the apparatus is set up. A Bunsen
burner can be used, but care should be taken
that the reflux rate is controlled. A hot-water
bath is not very suitable if the boiling points of
the reactants and product are too high.
4. Before you begin to heat the flask, ensure that
cold water is flowing from the tap to the base of
the condenser jacket and then out the top and
back into the sink.
5. Heat the flask and maintain reflux so that no
vapours are lost, and that the condensate drips
back into the reaction flask at about 2 drops
per second.
6. Reflux the mixture for at least 30 minutes
(or longer if time allows).
7. Turn off the heat and allow the apparatus to
cool. (Remove the heating mantle, hotplate or
water bath).

Isolation
You may wish to isolate the ester from the reaction
mixture. If so, then omit this section and proceed
with the optional extension.
8. Remove the boiling flask and carefully pour the
reaction mixture into a beaker containing
CHAPTER 10 ALKANOIC ACIDS AND ESTERS 231

PRACTICAL ACTIVITIES
70 mL of water. Stir with a glass rod. The
mixture contains the ester plus unreacted
alkanol and alkanoic acid. Compare the odour
of this solution with the odours of the original
reactants (see Results and analysis).
9. Clean up the equipment and workbench as
directed by your teacher. Keep the aqueous
mixture of the ester for further examination.

Results and analysis

1. Depending on the solubility of the ester you
have made, the aqueous mixture will either
remain as one phase, or separate into two layers.
(e.g. 1-butyl acetate is insoluble in water). If
separation occurs, the upper layer will be the
crude ester. It can be removed carefully using a
Pasteur pipette or by using a separation funnel.
2. Compare the odour of the ester (or the final
aqueous solution) with that of the original
alkanol and alkanoic acid. To do this you can
waft vapours towards your nose with your hand.
Describe what you smell in each case. Did the
ester have a distinctly different odour from that
of the reactants?
3. Explain how the ester could be extracted and
separated from the unreacted alkanol and
alkanoic acid.
4. Name the ester you have prepared and draw its
structural formula.

232 THE ACIDIC ENVIRONMENT

Conclusion
Write an appropriate conclusion for your
experiment.

Optional extension: Isolation of the ester

1. Add the reaction mixture to 30 mL of saturated
salt water in a beaker.
2. Pour the mixture into a separating funnel and
isolate the upper layer of crude ester.
3. Place the crude ester layer in a beaker and add
saturated sodium hydrogen carbonate to remove
any acid. Stop when fizzing ceases.
4. Isolate the ester once more using a separating
funnel.
5. Dry the ester using crystals of anhydrous calcium
chloride. Filter the mixture.
6. Set up a distillation apparatus and distil the
dried ester. Collect the distillate in a clean
beaker. The boiling points of the esters are:
ethyl acetate (77C)
1-propyl acetate (102C)
1-butyl acetate (127C)
1-pentyl acetate (147C)
ethyl butanoate (120C)
7. Compare the odours of the esters to those of the
original alkanol and alkanoic acid. Name the
ester you have prepared and draw its structural
formula.