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Esterification

Abstract

Production of esters through an acid-catalyzed nucleophilic
substitution reaction of carboxylic acids and alcohols can be done
through the Fischer esterification reaction
1
. The process is carried
on a reflux setup, where the evaporation of volatile chemicals is
prevented by boiling reactants while continually cooling the vapor,
returning it to the flask as a liquid
2, 3
. The reaction is reversible with
an equilibrium constant which only slightly favors the products, so
one of the reactants should be added in excess to drive the
equilibrium to the right and produce a decent yield. In this
experiment, it is aimed to produce isopropyl acetate using the
Fischer esterification method and calculate the percent yield of the
process. The boiling point range of the synthesized ester was 78-
80C and the percent yield was 28.0%.

Introduction

Esters are an example of a carboxylic acid derivative
4
. The carboxylic acid hydrogen is
replaced by another hydrocarbon group. Its general formula is:

(from http://upload.wikimedia.org/wikipedia/commons/f/f6/Ester-general.png)

Fischer esterification is a common method of synthesizing esters from carboxylic acids and
alcohols. Its net effect is substitution of an OH group to an OR group. All steps are reversible,
but since the equilibrium constant is nearly equal to 1, the equilibrium position can be driven to
either direction, depending on the condition of the reaction. Ester formation is highly favored when
an excess of alcohol is present
1
.

The goal in this experiment is to synthesize isopropyl acetate, an ester with a fruit-like
odor.


Experimental Details

To produce isopropyl acetate through Fischer esterification, a reflux setup has to be used.


Figure 1. A reflux setup
5


A reflux setup consists of a boiling flask with a condenser attached to its mouth. The side arm of
the boiling flask (if any) has to be closed. However, the condenser should not be stoppered to avoid
a potential explosion due to air pressure inside the system. Water flows from the bottom to the top,
where it exits on its way to the sink.

The reagents used were: 0.65 mol (49.6 mL) of isopropyl alcohol, 0.50 mol (28.6 mL) of
glacial acetic acid and 8 g of sulfuric acid. Boiling chips were also added to the mixture.

Upon refluxing, a brown solution was obtained. When this solution was collected, a
colorless liquid was collected. It formed two layers with water, with the distillate on top.

Two grams of sodium carbonate were added to the distillate (the ester) to neutralize the
acid which may have also been distilled. Ten mL of water was added to the ester because no
separate layer appeared in the neutralization process. The ester was washed with ice water, then
the water was removed, and then two separate 10-mL portions of 50% calcium chloride solution
were added to the ester. The washings were discarded. After washing, anhydrous calcium chloride
was added to the ester. After two days, two layers formed.

The ester was decanted from the water layer, and then a distillation process was carried to
the ester. The boiling point range was measured (78-80C) and the percent yield was calculated
(28.0%). The theoretical yield was 51.0 g, and the mass of the collected ester was 14.29 g.

Results and Discussion

The mechanism of the synthesis of isopropyl acetate is as follows
5
:
1. The carbonyl
oxygen of the
acetic acid
takes a proton
from
concentrated
sulfuric acid.
The proton
transfer gives
the oxygen a
positive
charge.
Resonance also
shows us that
the positive
charge is
delocalized on
the carbonyl
end, giving us
three possible
structures
(shown on the
right).

2. The positive
charge of the
ion is attacked
by one of the
lone pairs of
the alcohol
oxygen.


3. A proton is
transferred
from the
oxygen with
the positive
charge to
another
oxygen.

4. Water is lost
from the ion.

5. The hydrogen
attached to the
carbonyl
oxygen is
eliminated
from the
oxygen, thus
forming
isopropyl
acetate, the
final organic
product, and
regenerating
the sulfuric
acid catalyst.



From the theoretical yield and mass of collected ester previously recorded, the percent yield
can be computed as follows:
% =
14.29
51.0
= 28.0%

Conclusion

Isopropyl acetate was synthesized through the Fischer esterification process, but the yield
turned out to be low. This can most likely be accounted to some of the ester which evaporated
during reflux or the ester left from the solution inside the distilling flask (which should no
longer be distilled because distillation is never done to dryness).

References

1
McMurry, J. E. (2012). Organic Chemistry. Brooks/Cole, Cengage Learning.
2
Heating under reflux. (n.d.). Retrieved from
http://www.halesowen.ac.uk/chemistry/heating_under_reflux.htm
3
The Organic Chemistry Laboratory Web Pages - UW Madison. (n.d.). Retrieved from
http://www.chem.wisc.edu/areas/organic/orglab/tech/reflux.htm
4
Clark, J. (n.d.). An Introduction to Esters. Retrieved from
http://www.chemguide.co.uk/organicprops/esters/background.html
5
(n.d.). Retrieved from
http://www.chem.wisc.edu/areas/organic/orglab/images/tech/REFLUX.JPG
6
Clark, J. (n.d.). The Mechanism for the Esterification Reaction. Retrieved from
http://www.chemguide.co.uk/physical/catalysis/esterify.html

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