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CHEM 281L – Organic Chemistry Laboratory 1

Synthesis of Isopentyl Acetate

Objective:

In this experiment, you are going to reflux an alcohol with a carboxylic acid, in the
presence of an acid catalyst, to yield an ester and water. The formed ester (isopentyl
acetate) will then be purified by distillation in the next lab (exp # 5).

Introduction:

Isopentyl acetate, which is a clear colorless liquid, was first discovered as one of the
alarm pheromones of honeybees. Most esters have distinctive fruity tastes or
odours. Isopentyl acetate is sometimes called banana oil, due to its banana-like
flavour and smell. The primary way of synthesizing isopentyl acetate is by the
direct esterification (Fisher esterification) of acetic acid with isopentyl alcohol in the
presence of concentrated sulphuric acid as catalyst (see equation).

Chemical equation:

Alcohol Carboxylic acid Ester

O O
H2SO4
+ + H 2O
OH OH O

Fisher esterification is normally an equilibrium reaction. Since the equilibrium does

not favour the formation of the ester, it must be shifted to the right, in favour of the
product, by using an excess of one of the reagents. Acetic acid is used in excess
since it is less expensive than isopentyl alcohol and more easily removed from the
reaction mixture.
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In the isolation procedure, most of the excess acetic acid and the unreacted isopentyl
alcohol can be removed by extraction with water. Any remaining acid is removed by
extraction with aqueous sodium bicarbonate (NaHCO3). The isopentyl acetate is
then dried using sodium acetate.

Set-up:

The set-up for the experiment will be displayed in the lab, so no worries, the lab
instructor will walk you through its assembly at the beginning of the lab.

The set-up consists of a 5 mL conical vial, a magnetic spinvane, a reflux condenser,

and a drying tube. Once put together, the set-up should be secured to a ring stand
with a clamp.

Experimental:

In a 5 mL conical vial equipped with a spinvane, add 1.5mL of acetic acid and 1mL
of isopentyl alcohol (already pre-weighed), followed by 2~3 drops of sulphuric acid
(conc. H2SO4) as catalyst, and reflux the mixture for 75 minutes.

After the reflux is completed allow the reaction to cool down, then remove the
spinvane and add 2 mL of water. Stopper the conical vial, and shake it well. All
shaking in this experiment is to be done with ventilation. Allow the mixture to
settle and the layers to separate (be patient!), and then use a pipette to remove the
bottom layer (aqueous layer). This procedure is called a wash.
Add 1 mL of aqueous sodium bicarbonate solution (aq NaHCO3) to the mixture
then, using a spatula, stir the reaction mixture gently until it stops bubbling. Cap
the vial and shake it well, with ventilation. Again allow the mixture to settle and
remove the bottom layer (aqueous layer).
Repeat the wash with aqueous sodium bicarbonate solution two more times, but
without any stirring; just add the sodium bicarbonate, cap and shake the mixture.
After drying the isopentyl acetate with sodium sulfate, the product is transferred into
a vial, capped, labeled and handed to the TA for storing. The product will be
purified by distillation during the next lab period.
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Set-up Display: