Organic Chemistry Laboratory

Formal Report

Date Performed: April 08, 2015

Date Submitted: April 22, 2015
Institute of Biology, University of
the Philippines, Diliman, Quezon
City 1101

Instructor: Mariel Clores

Nucleophilic Acyl Subtitution: The Synthesis

of Ethers
J.M. Garcia
Synthesis of ester involves a reversible nucleophilic acyl substitution reaction of a carboxylic acid and an
alcohol. In this experiment, butyric acid (CH 3CH2CH2COOH) and ethanol (C2H5OH) was used to yield
ethyl butanoate (CH3CH2CH2COOCH2CH3), an ester which is responsible for the aroma and flavour of
fruits, pineapple specifically. The reaction was catalyzed with a strong acid, H 2SO4. A percent yield of
____ was obtained from the reaction of 6.0 mL butyric acid and 5.5 mL ethanol producing a 1.2 g of
ethyl butanoate. The product did not exactly give off a defined pineapple odor but since a relatively high
percent yield was obtained, it could be concluded that this reaction is efficient and is able to produce
esters. Better conduction of the experiment and use of a more accurate ratio of carboxylic acid to alcohol
is recommended for better results.

Chem 31.1 WFW/WFQR2, 326-327, 7:00-10:00 a.m.

Garcia, 2015| 1

Introduction

liquid dripped back to the flask at a rate of 2 drops per

second.

Esters are organic compounds that provide the

odors of fruits and flowers, and are used to
create
an
artificial
flavouring
in
fruity
beverages. Esters can also be used in industries
as organic solvents and making plastics because
it helps maintain plasticity and prevents it from
hardening.[2]
Esters are a class of compounds that are
composed of a carbonyl group attached to an
oxygen atom and are considered derivatives of
carboxylic acids. [1] In a process called the
Fisher esterification reaction, esters could be
synthesized by an acid-catalyzed nucleophilic
substitution reaction of a carboxylic acid with an
alcohol. [2] Other methods of ester synthesis
include reaction of carboxylic acids to alkyl
halides in basic medium, and the reaction an
acyl halide with an alcohol in pyridine. [3]
Fischer esterification reaction mechanism is
shown in Figure 1. Carboxylic acids are not
reactive
enough
to
undergo
nucleophilic
addition, so addition of a strong acid such as
HCl or H2SO4 is needed to enhance the
reactivity. The acid protonates the attached
oxygen to the carbon which makes this more
reactive because it gives way for the alcohol to
attack the carbon. The transfer of protons leads
to formation of OH. As the leaving group
detaches from the molecule, an ester is formed
with water as a side product [2]

(PICTURE)

Experimental
In a 25 mL round bottom flask, a ratio of 6.0 mL
butyric acid and 5.5 mL ethanol was mixed to produce
an ester with a pineapple like odor. Washed broken
glasswares was added and used as boiling chips to
prevent violent bubble formation. Glass boiling chips
were used instead of marble boiling chips because
marbles are formed by calcium carbonate which will
dissolve in an acidic medium since 2-3 drops of H2SO4
were added while swirling gently to acidify and
medium.
The flask was attached to a reflux condenser and
allowed to reflux for 45 minutes to complete the
reaction. Reflux set-up is shown in Figure 1. This was
done to prevent volatilization and to maintain a
temperature above the boiling point to which the

Figure 1. Reflux Set-up

The mixture was then cooled to room temperature and
poured into a 30 mL separatory funnel. The flask was
rinsed with cold water then the washing was poured to
the separatory funnel. The rinsing was repeated until
the aqueous layer was twice the volume of the organic
layer to make sure that all the mixture was in the
separatory funnel. To hasten the separation of layers,
a saturated NaCl solution was added. Then, the
aqueous layer was removed. This was repeated thrice,
but before the third washing was removed, solid
NaHCO3 was added until effervescence stopped
completely which indicated that the acid was
removed.
The organic layer was collected in a clean dry 100 mL
beaker. The make sure the crude ester is clear of
impurities, Na2SO4 was added until there is no
clumping. The ester was then transferred to a preweighed vial then the percent yield was determined.

Results and discussion

This is the meat of the paper. In most organic
chemistry papers, the results and discussion are not
separated, but woven together into a seamless
discussion that makes sense to the reader. The basic
pattern is to introduce data in a table or ChemDraw
figure, then refer to that data in a discussion. The best
way to go about this is to come up with questions that
you want to answer, then think about what figures or
tables would convey the data in the most
straightforward way. After doing this groundwork, you
can write the results and discussion section. Here are
the questions and data you must present as a
minimum. You can choose to include others as needed.
General questions for synthesis papers:
Did I synthesize my target compound?
What yield of the target did I get overall?
How pure is the final product?
Most importantly, WHAT DATA SUPPORT MY
CONCLUSIONS?

Organic Chemistry Laboratory

Formal Report
(Image)
Figure 1. Description of Image (if set up, name of the
set up)

Note 1: Along with, rationalise the procedures and

explain the mechanism behind the synthesis
Note 2: Inserting Graphics
Graphics should be inserted where they are first mentioned (unless
they are equations, which appear in the flow of the text).
The heading of the tables should be:
Table I. Title of Table

Conclusions and Recommendations

Summary of results and major conclusions. Are the
objectives attained?

References
1

The decryption of figures should be:

Chem 31.1 Section, Room No., Time

Citations here in the format A. Name, B. Name and C. Name, Journal

Title, Year Published, Volume (Issue Number), Page Number

Appendices
(a) Data Sheet with sample calculations

Authors Surname, 2015| Page Number