Title: Esterification

Aim: To make methyl ethanoate, ethyl ethanoate and isopropyl ethanoate

Apparatus: Glacial (concentrated) ethanoic acid (CORROSIVE) (25 ml), methanol (10ml),
ethanol (10 ml), isopropyl alcohol (10ml), concentrated sulfuric acid (CORROSIVE),0.5M
sodium carbonate solution (60 ml), boiling tubes (3), test tube rack (1), test tube holders (3), 50
ml beakers (4), 100ml beakers (1), water bath, 10ml measuring cylinder (2), droppers (2),
distilled water

Method: Into a clean, dry boiling tube, 10 drops of concentrated sulfuric acid was placed. Six
ml of glacial ethanoic acid was added to the boiling tube. Then, 4 ml of propan-2-ol was added to
the mixture. The contents of the boiling tube were shaken to ensure thorough mixing. The water
was heated in a water bath until the water began to boil. When this happened, the heating was
stopped. After, the boiling tube was left for 20 minutes in the hot water. If the mixture was
boiling in the tube, it was removed quickly from the water until the boiling stops. Then, the tube
returned to the hot water. The contents of the tube was then shaken gently and periodically to
ensure proper mixing. After 20 minutes, the boiling tube was carefully removed and placed in a
100ml beaker half filled with tap water. This was to allow the content to cool completely. When
the cooling was completed, 20 ml of 0.5M of sodium carbonate was added slowly to the boiling
tube in 5 ml portions. The boiling tube was shaken to ensure thorough mixing. A 100 ml beaker
was half filled with distilled water and the water was added into the mixture to help the
separation to occur. The product was smelled gently by wafting the odor towards the
experimenter’s nose with his or her hand. The experiment was repeated using methanol and
ethanol.
 Results:
TABLE SHOWING THE OBSERVATIONS AND IF ESTER LAYERS WERE FORMED
WHEN EXPERIMENTED WITH ISOPROPYL, METHANOL AND ETHANOL

Formation of Ester
Experiment Layer
with (addition of Observations
Na2CO3)
Before Heating After Heating Solubility in Smell of the
the Contents the Contents Distilled Water Ester Layer

Isopropyl Yes, ester layer was Solution was Remained the Insoluble Scent of fruits
(propan-2-ol) formed after 10 ml transparent. same. specifically
of Na2CO3 was pears.
added.
Methanol Yes, ester layer was Solution was Remained the Soluble Scent of nail
formed upon the transparent. same. polish remover
addition of Na2CO3. (distinct,
pleasant smell).
Ethanol Yes, ester layer was Solution was Remained the Insoluble Scent of nail
formed after 5 ml transparent. same. polish remover
Na2CO3 was added. (distinct,
pleasant smell).

Discussion:

Esterification is the process where esters are formed by reacting acid, carboxylic acid, with
alcohol or compounds containing the hydroxyl group. It normally occurs under acidic conditions
which in the experiment, sodium carbonate was added to the glacial ethanoic acid. In
esterification, water is also produced. An ester is a compound formed when the H on the COOH
group is replaced by an R group (methanol, ethanol, propan-2-ol etc). Esters can be used for
synthetic flavors, perfumes and cosmetics as well. It can also be used as solvents for paints and
varnishes.

In the experiment, isopropyl, methanol and ethanol were transparent. They remained transparent
after being heated. However, isopropyl and ethanol were insoluble in distilled water but
methanol was soluble in distilled water. Both, methanol and ethanol had distinct smell which was
of nail polish remover while isopropyl had a smell of fruits specifically pears scent. Isopropyl
and ethanol were insoluble in distilled water because isopropyl has a long carbon chain which
causes it harder to break bonds. There are many carbon atoms joined together so the bond is
stronger than the bonds in water. For ethanol, a double bond is present thus enabling the bond of
ethanol to be stronger than the water bonds and also it contain more than one carbon atom.
Methanol dissolved in distilled water because it has only one carbon and there are no double
bonds to strengthen the molecule, hence, it was soluble in distilled water. These reactions then
gave off the scents for methanol, ethanol and isopropyl respectively. The equations for the
reactions are as follows:

For isopropyl - CH3CH(OH)CH3 (aq) + CH3COOH (aq) ⇌ CH3CO2C3H7 (aq) + H2O(l) (forming
isopropyl ethanoate)

For ethanol - C2H5OH (aq) + CH3COOH (aq) ⇌ CH3CO2C2H5 (aq) + H2O (l) (forming ethyl ethanoate)

For methanol - CH3OH (aq) + CH3COOH (aq) ⇌ CH3CO2CH3 (aq) + H2O (l) (forming methyl
ethanoate)

In the experiment, the ease of separation was compared. It was observed that ethanol separated
easily, the isopropyl separated and then methanol was separated. So, the ease of separation was
from ethanol to isopropyl to methanol. This was so because each solvent had different boiling
points. Ethanol has a boiling point of 78 ⁰C while isopropyl has a boiling point of 82.5 ⁰C. The
ease of separation between the two was evident because ethanol evaporates more quickly
because it has a low boiling point. Methanol has a boiling point of 64 ⁰C. This ease of separation
was not seen because methanol boiling point is very low, hence it was recorded that it separated
slowly than the other two solvents. However, methanol ease of separation is very quick that the
methanol evaporates quickest than the other two solvent thus not allowing the experimenters to
observe correctly. So, the ease of separation should originally be from methanol to ethanol to
isopropyl.

In the experiment, the volume of the ethanoic acid was greater than alcohols, methanol, ethanol
and isopropyl, because the equilibrium does not favour the formation of esters. So, equilibrium
must be shifted to the right, to the product side, to balance the reaction with the help of a catalyst.
Hence, excess or more ethanoic acid was used. The mixtures were not allowed to be boiled in the
esterification reaction because the reaction will not occur. the solvents have low boiling points so
if they were left to boil, they would have evaporated. Hence, it was advised to not allow the
solutions to be boiled. Sulfuric acid was used in the experiment as an acid catalyst. It helped to
fasten up the process of ester formation knowing that the process is slow. The catalyst, sulfuric
acid was used to shift the excess ethanoic acid over to the product side creating equilibrium.
Sodium carbonate was used to attract H+ ions from the catalyst or remove the acid or the catalyst
from the mixture. This was done so that distilled water can be added and the separation of ester
layer and water can be seen.

One source of error that could have possible occurred in the experiment was evaporation. This
could have affected the experiment where the solvents had very low boiling points and can be
easily evaporated thus making it very hard for the experimenters to see if an ester was formed.
For instance, in the experiment, it was not seen that methanol formed an ester with ethanoic acid
but an ester was formed. This occurred because of the low boiling point of methanol and the sixe
of methanol. Methanol contains one carbon and has a low boiling point so it was soluble in
distilled water and the ester hence, was not visible.

Conclusion: In the experiment, methyl ethanoate, ethyl ethanoate and isopropyl ethanoate were
made and each was observed. It was observed that ease of separation was from ethanol to
isopropyl to methanol but the original ease of separation was to be from methanol to ethanol to
isopropyl. However, the observations were clarified each ester was made.