The Fischer Esterification

Martha Holt
Miholt1@catamount.wcu.edu
09/03/2020

ABSTRACT

Abstract [5pts] – The written abstract should briefly state what was done, significant results, and a brief
conclusion. Give percent yield of product and comment on purity, if possible. This should be short and to the
point - no more than 75 words.

Introduction [10 pts] Microwave irradiation is a form of energy

Fischer esterification is used to synthesize that takes only minutes to heat reactions to certain

the ester isopentyl acetate through an acid-catalyzed temperatures that other heating techniques would

esterification reaction. Esterification is used require hours for. This technique was not used in

commercially to produce esters when carboxylic organic laboratories until 1986 when Professors

acids are heated with alcohols in the presence of an Richard Gedye, Raymond J. Giguere, and George

acid catalyst, usually sulfuric acid Esterification is Majetich made their publications in regard to this

used for industrial use including, pharmaceuticals, technique. It was not commonly used in this

solvents of paints, adhesives, bioplastics, flavors, beginning because of its lack of control compared to

cosmetics, pesticides, food, and biodiesel. This other techniques that are commonly used in

technique is used for items that humans use every laboratory. Solid supports can be applied to absorb

day, which shows its significance in understanding. energy from the microwaves that easily transfer the

energy to the reaction taking place. Water is also

used at times with this technique to eliminate

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microwave energy not used by the reaction. These added to separatory funnel with the contents from

techniques enabled the microwave to not be the microwave placed on top along with diethyl

damaged during heating. The heating mantles use ether and mixed well. Organic layers were separated

energy to warm the mantles and then when this in a separatory funnel.

warms the vessel will warm. The vessel warming

Acetic Acid was added in excess in the
will warm the reaction mixture until everything is
reaction because the equilibrium must be shifted in
relatively the same temperature. Every chemical
favor of the products so the ester is favored. Acetic
absorbs the energy differently due to their polarity,
acid is more easily removed from the reaction
which will be affected more or less by the changing
mixture. There is an effervescent reaction as the
microwave field. The microwaves have went from
acetic acid and sulfuric acid are neutralized by the
only being used for industrial needs, like food
bicarbonate solution that is added.
processing, to more analytical use for digestion and

extraction of samples. This experiments success can be observed

through the comparison of the calculated theoretical

The mechanism of the Fischer esterification
yield and the actual yield. The theoretical yield of
reaction begins with the protonation of the carbonyl
products was 2.99 g of isopentyl acetate. The actual
oxygen atom by the acid catalyst. These atoms
yield of products was 2.48 g of isopentyl acetate
rearrange to form the final product of ester isopentyl
product. The equation to calculate percent yield is as
acetate. The purpose of this lab is to synthesize the
follows: % yield = (actual yield/theoretical yield) x
ester isopentyl acetate, via an anid-catalyzed
100%. With the yields plugged in to this equation it
esterification reaction in a microwave synthesizer,
looks like this: (2.48 g / 2.99 g) x 100% = 83 %.
and characterize the structure of the product by IR
This is a good percent yield; however, the closer the
spectroscopy.
percent yield is to 100, the better. This difference

Results and Discussion (30 pts) could have been due to incomplete reactions or loss

Acetic acid and isopentyl alcohol were of sample during recovery. With knowing that our

mixed, then drops of sulfuric acid was added and percent yield was relatively high, it gives a good

placed into microwave until ready when it held indication that the IR spectrum will give us good

120°C for five minutes. A bicarbonate solution is data to identify the compound.

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Figure 1. IR spectra of isopentyl acetate derived
during lab.
Figure 2. Standard IR spectra of isopentyl acetate.
Figure 3. Standard IR spectra of isopentyl alcohol.
When observing figure 2, the C=O stretch is shown
close to 3000 cm-1 and C-O-C stretch is shown close
to 1750 cm-1. This can be comepared to the same
two peaks that are labeled in figure 1, that was
derived in lab. This indicates that the IR spectra
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from lab has the correct product because the
ditinguishing peaks are the same. To make sure that
there is no product left over, we can observe the
peaks in figure 3. In figure 3, there is no peak at
1750 cm-1 which indicates that there is no C-O-C
stretch that would be found in the product. This
allows us to conclude that there is no reactants left
in the final product.
Conclusion (5 pts)
In conclusion, this lab was successful due to the two
components measuring the accuracy of the product.
The percent yield being 82.9% indicates that almost
all of the product that was expected was produced.
The comparison of IR spectrums indicates that there
is no reactant left over in the products. Also, the IR
spectra of the isopentyl acetate has the expected
peaks for this compound. This is an interesting lab
because you can compare the reactants to its
products in multiple ways to test the accuracy of
your experimental techniques.
Experimental (15 pts)
Acetic acid (25 ml), 2.5 ml of isopentyl alcohol, and 10
drps of concentrated sulfuric acid was added and placed
intomicrowave carousel. The reaction was heated until
solution stayes at the same temperture for 5 minutes, then
the reaction was cooled. This was then placed into a
seperatory funnal along with 10 ml of sodium bicarbonate
and seperated leaving the organic layer on top, then do
the same thing with 5 ml of sodium bicarbonate. The
organic layer is then seperated with with 5 ml diethyl
ether two times. Calcium carbonate was then added to the
organic layer which allowed it to dry and removed with
gravity filtration. The ether was then removed with rotary
o Indicate which IR bands you used to confirm
the presence of this functional group.
o Clearly assign important bands to specific
bonds of the molecule. Ex C=O stretch, C-O-C
stretch
Attach literature spectra (obtained from the web)
of the two starting materials, labeled with each
compound’s structure.

evaporation.

Isopentyl acetate. Theoretical yield = 2.99 g. D =

130.19 g/mol. Eqv = 1. IR : C=O stretch, C-O-C

stretch.

References:

Chemguide.co.uk. 3030. Preparation of Esters.

[online] Avaliable at:

<https://www.chemguide.co.uk/organicprops/esters/

preparation.html#:-:text=Es...[Accessed 11

September 2020].

Scientificdirect.com. 2020. Esterifiction. – An

Overview | Scientificdirect Topics. [online]

Available at: Fischer Esterification Grading Key

,https:www.sciencedirect.com/topics/chemistry/ester Notebook
Purpose/Table ___/ 5 pts
ification#:-:text=Esterification… [Accessed 11
Observations/Conclusion ___/ 5 pts
September 2020]. Formal Lab Report
Abstract and Figures ___/10 pts
Webbook.nist.gov/cgi/inchi?
Background and Intro ___/10 pts
ID=C123922&Type=IR-SPEC&Index=2. [Accessed
Results and Discussion
11 September 2020]. Excess reagent/H2SO4 ___/ 5 pts
purification ___/ 5 pts
Supplemental Materials (15 pts)
yield – theoretical, percent ___/ 5 pts
Attach the IR spectrum of your product. IR interpretation ___/15 pts
o Draw the stucture of your product on the
Conclusion ___/ 5 pts
spectrum.
o Indicate which functional groups should appear Experimental ___/15 pts
in the spectrum of your product. References ___/ 5 pts

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IR spectra (3) ___/10 pts
Spelling/Grammar/Format ___/ 5 pts
# days late ___  5% – ___ pts
Total points ______ /100

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