Activity 9

WMSU-ISMP-GU-002.
00
Effective Date: 7-DEC-2016
Activity No. 9
ESTERIFICATION REACTION:
SYNTHESIS OF ISOPENTYL ACETATE
Introduction
Isopentyl acetate (also known as isoamyl acetate) is an ingredient of a

bee’s highly irritating stinging device. The bee ejects approximately one
microgram per sting. When a bee stings an intruder, the said pheromone is
also secreted with the venom. In addition, this then serves to attract other bees
to become aggressive and attack the intruder.
Concepts/ Explanation
In this activity, isopentyl acetate (which has the odor of bananas), is

synthesized under a Fischer esterification reaction from acetic acid and
isoamyl alcohol under a strong acid as a hydrogen ion catalyst. The overall
reaction is presented as follows:
The following is the most probable mechanism of the acid- catalyzed

formation of isoamyl acetate:
Prepared by the Organic Chemistry Committee

Chemistry Department, College of Science and Mathematics
Western Mindanao State University
WMSU-ISMP-GU-002.00
The reaction, like most ester formation, do not proceed rapidly even in
the presence of an acid catalyst. Thus, they must be heated for an extended
period.
Boiling is not an option as the reactants are very volatile and would
simply convert into gas before any substantial number of products are formed.
Thus, to ensure that they do not simply volatilize after heating the reaction
vessel, the reactants should continuously recondense and drop back to its
container.
Procedure
CAUTION: Careful in using both glacial acetic acid as well as concentrated

sulfuric acid, as they are both corrosives. Gloves, laboratory
safety goggles as well as masks must be always worn when
using these reagents.
1. Add 5.4 mL isoamyl alcohol in a clean and dry 100- mL round

bottomed, single- necked flask. After which, carefully add 8.5 mL
glacial acetic acid. Place the resulting solution in a water bath filled
with cold water.
2. Add 1 mL of concentrated sulfuric acid slowly and carefully into the

flask, then place a few boiling chips. Heat in the flask in expected to
form
3. After allowing the flask to cool down, assemble it in a reflux apparatus

setup as shown below. The alcohol lamp in the sample can be replaced
with a water bath in a hot plate. Have the setup checked first by the
instructor before proceeding.
Figure 1. Reflux setup for the synthesis of isopentyl acetate.

WMSU-ISMP-GU-002.00
4. Heat the flask containing the solution to boiling under reflux for 1- 1.5
hours. After the reflux operation has been completed, remove the flask
and cool it in an ice bath for about 10-15 minutes.
5. After cooling, pour carefully the contents in the flask into a 250- mL
separatory funnel. Rinse the reaction flask with 25 mL of cooled
distilled water and pour the washing into the separatory funnel. Note
that the boiling chips should not be allowed to be transferred with the
mixture into the separatory funnel.
6. Shake the separatory funnel carefully for a few minutes to allow the
separation of water and isopentyl acetate. Drain off the discard the
water solution. If the organic phase and water solution do not separate
rapidly, add 25 mL of saturated NaCl solution and shake to stimulate
separation.
7. Extract the isopentyl acetate solution with one 25- mL portion of 10%
Na2CO3 solution. After which, allow the separatory funnel to stand in
an upright position for a few minutes. Again, drain off any lower
water phase present.
8. Purify the isopentyl acetate with drying with anhydrous sodium sulfate
and is separated using simple filtration. The ester is expected to be
collected in the form of a filtrate.
9. If time permits, further purify the synthesized compound by simple

distillation. Collect the fraction that distills at 138- 142 °C. Either of
which, the final product should be collected in a pre- weighed and
properly- labeled 25 mL vial. Determine the weight of isoamyl acetate
and calculate its percent yield.
Cleaning Up
1. Dilute the water layer in the separatory funnel with copious amount of
water and flush it down the drain.

WMSU-ISMP-GU-002.00
Guide Questions
1. What is the purpose of the reflux setup in the synthesis of the liquid
ester?
2. How is the adding of NaCl in the separatory funnel promotes the

separation of two layers in the mixture?
3. Why is carbon dioxide produced during the extraction procedure after

the addition of sodium carbonate? Write a balanced equation that
produced it.
4. Concentrated sulfuric acid is used as a catalyst for the esterification of

acetic acid in the preparation of isopentyl acetate. Why is the sulfuric
acid needed if another acid (i.e. acetic) is already present?
References
1. Pavia, D.L., Lampman, G.M., Kriz, G.S. & Engel, R.G. Microscale
and Macroscale Techniques in the Organic Laboratory. (2002). CA,
USA: Brooks/Cole Cengage Learning.
2. Miller, J.A. & Neuzil, E.F. Modern Experimental Organic Chemistry.

(1982). Western Washington University, USA: D.C. Heath and
Company.
3. Mayo, D.W., Pike, R.M. & Forbes, D.C. Microscale Organic

Laboratory with Multistep and Multiscale Syntheses Fifth Edition.
(2011). NJ, USA: John Wiley & Sons, Inc.


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WMSU-ISMP-GU-002.

Isopentyl acetate (also known as isoamyl acetate) is an ingredient of a

In this activity, isopentyl acetate (which has the odor of bananas), is

The following is the most probable mechanism of the acid- catalyzed

Prepared by the Organic Chemistry Committee

CAUTION: Careful in using both glacial acetic acid as well as concentrated

1. Add 5.4 mL isoamyl alcohol in a clean and dry 100- mL round

2. Add 1 mL of concentrated sulfuric acid slowly and carefully into the

3. After allowing the flask to cool down, assemble it in a reflux apparatus

Figure 1. Reflux setup for the synthesis of isopentyl acetate.

9. If time permits, further purify the synthesized compound by simple

Prepared by the Organic Chemistry Committee

2. How is the adding of NaCl in the separatory funnel promotes the

3. Why is carbon dioxide produced during the extraction procedure after

4. Concentrated sulfuric acid is used as a catalyst for the esterification of

2. Miller, J.A. & Neuzil, E.F. Modern Experimental Organic Chemistry.

3. Mayo, D.W., Pike, R.M. & Forbes, D.C. Microscale Organic

Prepared by the Organic Chemistry Committee

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