Drexel University

Preparation of an Ester

LAB REPORT #5
Tuesday, January 19, 2016

INTRODUCTION
Esters are organic compounds synthesized through a condensation reaction involving a
carboxylic acid and an alcohol. In this reaction, the carboxylic acid loses one hydrogen atom and the
alcohol loses one hydroxyl group. As a result, this esterification reaction produces the products of an
ester and one water molecule, due to the reaction between the hydrogen atom and hydroxyl group.
Below, Figure 1 shows the general formula of each organic compound and Figure 2 shows the overall
condensation/esterification reaction.

Carboxylic Acid

Alcohol

Ester

Figure 1 Organic Compound General Formulas

RCOOH (aq) + HOOCR(aq) RCOOOCR(aq) + HOH (aq)

Acid anhydride

Figure 2 Condensation/Esterification Reaction

To further elaborate on Figure 1, the general formula of an ester is mainly due to the reaction of a
carboxylic acid and an alcohol. As shown above, the carboxylic acid functional group involves a carbon
atom double-bonded to an oxygen, which makes it a carbonyl group, Furthermore, an alcohol group
and an R group, which represents a variable for a particular chemical formula, are branched off from
this carbonyl group. As for the alcohol functional group, theres a hydroxyl group attached to an arbitrary
R group. In terms of the ester functional group, the hydroxyl group of an alcohol and the hydrogen
atom of a carboxylic acid are removed within the condensation/esterification reaction, which results in

the formation of water, as mentioned before. In addition, the ester functional group involves both R
groups from the carboxylic acid and alcohol and the carbonyl group remain intact.
With nomenclature, esters are slightly difficult to name compared with other functional groups and
organic molecules. Since an ester is a reaction between a carboxylic acid and an alcohol, the
nomenclature of these two organic compounds are slightly altered to fit the needs of an ester. An ester is
named in two parts and the first part represents the alcohol as an alkyl group, as it replaces the H in the
hydroxyl group. For example, methanol would become methyl. For the second part, the ic in the
carboxylic acid is replaced with ate and the acid is dropped at the end. For example, pentanoic acid
would become pentanoate. Figure 3 shows an example of how esters are properly named.

Figure 3 Ester Nomenclature

The general use of esters is typically common within modern society. Esters tend to have a sweet
aromatic fragrance and are used in most artificial flavoring substances and scented products. For
example, methyl butanoate and ethyl butanoate are common within certain types of fruits, as they largely
account for the overall smell and taste. Their sweet smell and aromatic fragrance account for most of the
common, everyday uses that people generally take into consideration.

OBSERVATIONS & DISCUSSION

Description of Observations
The experiment was completed in an incredibly short amount of time, approximately 6 minutes for the
entire reaction to subside. Based off the observations of the overall reaction, there werent any prominent
phase changes or color changes. Once the experiment was finished, however, the odor was quite unfamiliar
at first. It had a sharp and quite distinct scent. Thereafter, as the odor began to evenly distribute throughout
the room, it became easily identifiable, as it had a strong scent of bananas. Based off these results, the
process of classifying the synthesized ester was underway, as it was found to be isoamyl acetate. This ester
is made from isoamyl alcohol and acetic acid. It was highly suspected that the odor was quite unfamiliar at
first due to the strong scent of the acetic acid, as it does share a few properties with that of vinegar.
Possibly, the most interesting observation of this experiment was the fact that it took such a short amount of
time to complete.

Fundamental Factors
Throughout the experimental procedure, there were certain factors that greatly influenced the overall
overcome of the experiment. For instance, a cold finger condenser was utilized since the beginning of the
experiment and its main purpose was to reflux the reaction. To further elaborate, refluxing a reaction means
that the initial vapor, which enters the system, undergoes condensation and returns as condensate. This
helps to keep the liquid volume stable within the reaction, as most of it begins to evaporate due to the high
temperatures as its boiling. Another key element of the experiment was Drierite, a desiccant that assists in
the removal of excess water. During the reaction, water is formed along with the ester, as mentioned before
in the Introduction. This water can be quite detrimental, as it can combine with the resulting ester and
produce an alcohol and a carboxylic acid instead. Therefore, Drierite helps with removing this excess water
by drying it up in the forms of small crystals. The final and most important factor of this experiment is sulfuric
acid. The effects of sulfuric acid are not physically visible, however, it greatly contributes to the prevention of

de-esterification, which is when water combines with the resulting ester to return it as a carboxylic acid and
an alcohol. It does this by combining with the water, which helps it act as an addition acid to the reaction
and speeds up the synthesis of the ester. These fundamental factors might have been overlooked from the
beginning, however, they greatly contribute to the overall synthesis of the resulting ester.

Calculations
Conversion of volume (mL) into mass (grams)
isoamyl alcohol 18.1 mL x 0.810 g/mL = 14.661 g
acetic acid 9.5 mL x 1.049 g/mL = 9.9655 g
Conversion of mass (grams) into moles (mol)
isoamyl alcohol 14.661 g/88.15 g/mol = 0.1663187748 mol
acetic acid 9.9655 g/60.05 g/mol = 0.1659533722 mol
Molar ratio of alcohol to acid
isoamyl alcohol 0.1663187748 mol
acetic acid 0.1659533722 mol
ratio = 0.1663187748 mol/0.1659533722 mol = 1.002201839
As shown from the results above the esterification ratio from the reaction between isoamyl alcohol
and acetic acid is 1:1.

CONCLUSION
In a vast world of chemistry, organic compounds make up an entirety of the common elements
seen within modern society. The synthesis of esters provided a new perspective, as one does not
ponder upon the originality of certain smells and tastes. Moreover, this experiment has contributed to the
overall development of easily understanding the properties of a carboxylic acid and an alcohol, as they
are used in a condensation/esterification reaction. Elements such as sulfuric acid and a desiccant, such
as Drierite, also contribute heavily to the outcome of the experiment. In addition, these experimental
factors have provided a theoretical analysis to most of the effects and causes of organic compounds, as
their functional groups and reactions clearly explain and define them. Ultimately, organic compounds are
heavily used within modern society and understanding its uses is quite interesting.