Title: Esterification

Aim: To make ethyl ethanoate and isopropyl ethanoate.

Apparatus: Glacial (concentrated) ethanoic acid (CORROSIVE) (15 ml), ethanol

(10 ml), isopropyl alcohol (10ml), concentrated sulfuric acid (CORROSIVE),0.5M
sodium carbonate solution (40 ml), boiling tubes (2), test tube rack (1), test tube
holders (2), 50 ml beakers (4), 100ml beakers (1), water bath, 10ml measuring
cylinder (2), droppers (2), distilled water.

Method: 10 drops of concentrated sulphuric acid were placed into a clean, dry
boiling tube. 6 ml of glacial ethanoic acid was added to the boiling tube. 4ml of
propan-2-ol was added to the mixture. The contents of the boiling tube were
shaken to ensure thorough mixing. The water in the water bath was heated until the
water began to boil, then the water bath was heated no longer. The boiling tube was
placed and left in the hot water for 20 minutes. When the mixture in the tube began
to boil, the boiling tube was quickly removed from the water until the boiling
ceased, and was then returned to the hot water bath. The contents of the boiling
tube were shaken periodically to ensure proper mixing. After 20 minutes, the
boiling tube was carefully placed in a 100ml beaker that was half-filled with tap
water and was allowed to cool completely. When cooling was complete, 20 ml of
the 0.5 M sodium carbonate was slowly added to the boiling rube in 5 ml portions.
The boiling tube was shaken well to ensure thorough mixing. The product was
smelled by gently wafting the odor towards the experimenter’s nose with the
experimenter’s hands. The above procedure was repeated using ethanol instead of
propan-2-ol.
 Result:
TABLE 1: THE OBSERVATIONS MADE DURING THE STAGES IN THE
ESTERIFICATION OF ETHYL ETHANOATE AND PROPYL
ETHANOATE.
Carboxylic OBSERVATIONS
acid and
alcohol
combined
respectively

After mixing During heating During the addition of Whether or The relative Scent of
carboxylic acid the boiling tube NaCO3 in 5 ml not a layer ease with product
and alcohol with in the water bath portions formed which the
H2SO4 in the layer formed
boiling tubes

Ethanoic Clear, transparent No boiling was Effervescence was Layer formed Not very easy Sweet fruity
acid + solution observed observed observed. A very thin smell, the
propan-2-ol transparent layer slowly scent of pears.
separated above the
solution after the third 5
ml addition.

Ethanoic Clear, transparent The solution Effervescence was Layer formed Very easy Sweet fruity
acid + solution observed began boiling observed. A thin layer smell, the
ethanol several times began to form above the scent of
solution on the initial 5 grapes.
ml addition.

Discussion: Esterification refers to a type of condensation reaction which occurs

when a carboxylic acid reacts with an alcohol. Esterification produces an ester and
water. The functional group of esters is the ester group/linkage (-COO-). In the
experiment conducted, the esters ethyl ethanoate and propyl ethanoate were
produced by reacting ethanoic acid and ethanol, and ethanoic acid and propan - 2 -
ol respectively. The volume of the ethanoic acid was greater than the alcohol in the
esterification process because the carboxylic acid is more easily removed from the
reaction mixture. Hence by Le Chateleir’s principle, using excess ethanoic acid
served to force the reaction equilibrium to the right in favor of the ester. Because
esterification reactions are generally slow and reversible, small quantities of esters
are produced. Thus concentrated sulphuric acid is used in esterification reactions.
The concentrated sulphuric is added for two reasons; It acted as a catalyst to speed
up the slow reaction and it removes the water produced in the condensation
reaction. By Le Chateleir’s principle, this forwards the reverse reaction and
increases the small yield of the ester. Since esterification reactions are also
endothermic, the heat from the water bath for 20 minutes also served to favor the
forward reaction in favor of the ester by Le Chateleir’s principle. The mixtures in
the test tubes were not allowed to boil because the reagents of the mixtures and the
esters are particularly volatile and consequently, they vaporize easily. Hence the
mixtures were not allowed to boil to prevent the reagents from evaporating before
the ester products were formed. After cooling the boiling tubes on heating in the
water bath for 20 minutes, sodium carbonate was added in 5ml portions to the
boiling tubes. The sodium carbonate (a base) served to neutralize the sulphuric acid
(an acid) added as a catalyst. The occurrence of this neutralization reaction was
physically expressed by the effervescence which was observed on adding the
sodium carbonate in 5 ml portions. The balanced chemical equation for the
neutralization of the sulphuric acid using sodium carbonate is as follow:
H2SO4 (aq) + Na2CO3 (aq) → Na2SO4 (aq) + CO2 (g) + H2O (l)

Esters are virtually soluble in water and tend to form a thin layer on the surface
because they have low densities than the alcohols and carboxylic acids used to
make them. Excess acid and alcohol used both dissolve and remain below the ester
layer.
The balanced chemical equation for the synthesis of ethyl ethanoate from ethanoic
acid and ethanol catalyzed by sulphuric acid is as follows:
Conc. H2SO4
Ethanoic acid + ethanol ⇌ ethyl ethanoate + water
Heat

Conc. H2SO4
CH3COOH (l) + C2H5OH (l) ⇌ CH3COOC2H5 (l) + H2O (l)
Heat
The balanced chemical equation for the synthesis of propyl ethanoate from
ethanoic acid and propan -2- ol catalyzed by sulphuric acid is as follows:

Conc. H2SO4
Ethanoic acid + propan - 2 - ol ⇌ propyl ethanoate + water
Heat

Conc. H2SO4
CH3COOH (l) + CH3CH(OH)CH3 (l) ⇌ CH3COOC(CH3)2H (l) + H2O (l)
Heat
A thin layer began to form above the solution in the test boiling to which ethanoic
acid and ethanol were added on the initial 5 ml addition of sodium carbonate The
very thin layer above the solution in the boiling tube was the ester ethyl ethanoate,
while the solution below was excess ethanoic acid and ethanol.
On the other hand, a very thin layer began to form above the solution in the test
boiling to which ethanoic acid and propan-2-ol were added only after the third 5 ml
addition of sodium carbonate. The very thin layer above the solution in this boiling
tube was the ester propyl ethanoate, while the solution below was excess ethanoic
acid and propan -2- ol. The propyl ethanoate ester formed with greater ease and
was of greater yield than the ethyl ethanoate ester. The ethyl ethanoate ester had a
fruity scent, the smell of grapes, while the propyl ethanoate ester also had a fruity
scent, but the scent of pears.

Because esterification reactions are slow and reversible heat is required which
would favor the forward reaction to increase the yield of the ester, since the
reaction is also endothermic. If the heat supplied to the boiling tubes was
insufficient, or the 20 minute time period for which the boiling tubes were left in
the waster bath was insufficient then this may have decreased the yield of the ester,
or affected whether the ester formed or not.

Conclusion: Ethyl ethanoate and propyl ethanoate were made by reacting ethanol
and propan -2 - ol, each with ethanoic acid.