Section 097

Dr. Balsubramaniam
Preparation of an Ester Lab
 Introduction

The purpose of this laboratory experiment is to react molecules together to synthesize and
identify a specific product based on smell. Then, the masses of reactants utilized in the reaction
can be used to stoichiometrically prove or disprove the conclusion.
The molecules in this experiment are reacted to create a product known as an ester. Esters
are aromatic compounds and are utilized to create the flavoring or scents of fruits in certain foods
and drinks. Moreover, they can be used to create the odors associated with air fresheners or
scented candles. Structurally, these esters can be identified in their formulas by the ester
functional group comprising of a carbonyl group bonded to an oxygen and located between two
“R groups” of the molecules chain. To create this defining functional group an alcohol (hydroxyl
group) and a carboxylic acid (carboxyl group and hydroxyl group) are reacted together in a
dehydration process, which requires a catalyst and heat. Seen in the figure below, these two types
of molecules form an ester bond between the R-O and R’-CO- fragments to join through
dehydration of the O-H in the alcohol and the H in the carboxylic acid. As a result, H2O is
separated out of the reactants and become a by-product of the ester formed.

As observed in the reaction, only the functional groups change within the reactant
molecules. The R groups – the alkyl groups of each molecule – stay the same. Although not
included in the figure above, each esterification reaction is reversible and exists in a state of
chemical equilibrium. Furthermore, these reactions can be sped up by the input of a catalyst,
such as an acid (H+) in the forward reaction and the input of a base (OH-) in the reverse reaction.
Because this reaction can be catalyzed so easily with the ions of water, it can be easily reversible.
Consequently, some specific uses that involve the contact of water can limit esters as their
decomposition can result in often unpleasantly scented odors.
Organic compounds have often complex names due to their molecular specificity and
large number of combinations. To name esters the oxygen bonded on both sides to carbons is
located. Then, the largest chain of carbons bonded to the oxygen is numbered. The alkyl group is
written first and then the IUPAC name for the longest chain is added with an “-oate” ending
instead of a “-e” ending. If attached to a ring, the ester is named as a substituent.
 Discussion
In order to synthesize a given ester molecule, a specific material set up was utilized in the
laboratory. A measured volume (mL) of alcohol along with a measured mass (g) of acid was
poured into an Erlenmeyer flask where the reaction takes place. Next, a volume (8-10 drops) of
H2SO4 was dropped into the flask to serve as the catalyst for the reaction. To prevent the reaction
from escaping, multiple cold finger condensers were created by inserting ice into test tubes.
These condensers were placed in fixed positions in the neck of the Erlenmeyer flask and replaced
once all ice was melted. Because esterification reactions are easily reversible due to the presence
of water, a desiccant called Drierite was utilized to absorb excess water. Providing the ideal heat
required for the reaction to take place, a hot plate and magnetic stir rod were used to heat and
continuously mix while the reaction occurred.
During the approximate 40 minutes that the solution reacted, it could be observed that
there was an obvious color change. The solution was originally a cloudy gray color, but after
time passed the reaction mixture became transparent. Phase changes also occurred during the
time of the reaction. The solution kept transition from liquid to gas phase, but the cold finger
aided in the condensation of the gas created back to liquid. When replacing the cold fingers
during the reaction, the flask smelt like banana, cinnamon, and then strawberry. After sufficient
time elapsed and the reaction had run its course the smell of strawberry was evident from the
flask. Based on the odor, the ester was assumed to be methyl cinnamate. Since the ester created
was assumed to be methyl cinnamate, then the reactants used were methanol and cinnamic acid.
Chemical Equation:
CH3 – OH (aq) + C6H5CHCH-COOH (s)  C6H5CH=CH-COOH (aq) + H2O (l)
Calculations
Constants:
Volume of Methanol (Alcohol B): 6.80 mL
Mass of Cinnamic Acid (Acid A): 2.50 g

Mole Conversion for Methanol:

Mass of Methanol = Volume * Density

Mole Conversion for Cinnamic Acid:

Mass of Acid
Moles of Acid =
Molar Mass
2.50 g
Moles of Acid = g
148.16
mol
Moles of Acid = 0.0169 mol

Molar Ratio:
Moles of Methanol
Molar Ratio =
Moles of Acid
0.162 mol
Molar Ratio =
0.0169 mol
Molar Ratio = 9.58

Conclusion
The goal of this laboratory experiment was to react an acid and an alcohol to produce an
ester. The specific type of ester was to be identified by the odor given off once the reaction ran
its course. Based on the odor, the ester produced was determined to be methyl cinnamate. From
this conclusion, the reactants were ascertained to be methanol and cinnamic acid. Through
stoichiometric calculation, the molar ratio of methanol to cinnamic acid was established as 9.58.
The molar ratio that was calculated based on the experimental results confirms the theoretical
molar ratio of methanol to cinnamic acid, which is 10.00. Although the experimentally
determined molar ratio does deviate from the theoretical value, it is close enough that the same
conclusion can be drawn. A possible error that could have created the small deviation in molar
ratios is the masses of each reactant gathered. If the number of moles of methanol used was less
than the theoretical amount, then the molar ratio would have decreased. Additionally, if the
number of moles of cinnamic acid was less than the theoretical amount, then the molar ratio
would also have decreased. Another possible experimental error could be related to the use of the
same scooper to collect acid for each group. Because each group had different acids and every
group used the same scoop, some cross-contamination of the sample could have occurred. As a
result, the collected sample of acid would have been less than the theoretical amount leading to a
smaller molar ratio.
From the experiment, the esterification process was learned. More specifically, the
reactants – an alcohol and an acid – to produce an ester with excess water. Also, the functional
groups involved with the creation of an ester and the catalysts needed for the forward and reverse
reaction were learned through the experiment. Experimentally, the techniques of measuring
quantities, mixing, combining solutions, recording data, and observing reactions were utilized in
this experiment.