ORGANIC

CHEMISTRY

Organic Chemistry Laboratory CH 200L (2014 - 2015) Experiment # 2

Preparation of Isoamyl Alcohol through Fischer reaction and Extraction of Isoamyl Acetate
Producing Synthetic Banana Flavor
Raymond Baladad, Kenny Bautista*, Alyssa Capuchino, Cham Chan
Department of Biological Sciences, College of Science
University of Santo Tomas, Espaa Street, Manila 108
Date Submitted: August 19, 2014
Key Words:
Esters - are usually derived from an inorganic acid or organic acid in which at least one -OH (hydroxyl)
group is replaced by an -O-alkyl (alkoxy) group. Commonly esters are derived from carboxylic acids
and alcohol.
Fischer Reaction - special type of esterification by refluxing a carboxylic acid and an alcohol in the
presence of an acid catalyst.
Isoamyl Acetate - also known as isopentyl acetate, is an organic compound that is the ester formed from
isoamyl alcohol and acetic acid. It is a colorless liquid that is only slightly soluble in water, but very
soluble in most organic solvents.
Abstract
Esters are groups of compound that generally possess distinctive odor like fragrances and fruit flavors.
In this experiment, we will use isoamyl alcohol to produce an ester that produce smell of fruit flavors. It
will involve refluxing of isaomyl alcohol with acetic anhydride and acid catalyst and extraction of
isoamyl acetate. The isoamyl acetate is the finished product that produces the smell of banana flavor.
I. Introduction
The word flavor is used to describe the overall sensory effects of a substance taken
into the mouth. Flavor may involve tactile, temperature, and pain sensations, as
well as smell and taste. Many fruits, flowers, and spices contain esters that
contribute to their characteristics flavors an ester is an functional group produced
from the condensation of an alcohol with a carboxylic acid, and are named based
on these components. They are characterized by a carbon bound to three other
atoms: a single bond to a carbon, a double bond to an oxygen, and a single bond
to oxygen. Most volatile esters have strong, pleasant odors that can best be
described as fruity. Some esters with flavors characteristic of real and fantasy

are propyl acetate pears, octyl acetate oranges. The ester that we will prepare
in this experiment, isopentyl acetate, has a strong banana odor when undiluted
and an odor reminiscent of pears in dilute solution. It is used as an ingredient in
artificial coffee, butterscotch, and honey flavourings, as well as in pear and banana
flavorings. Esters are often prepared by the Fischer esterification method, which
involves heating a carboxylic acid with an alcohol in the presence of an acid
catalyst. The acid catalyst is used to increase the rate of reaction, which would
otherwise require a much longer reaction time. The scope for this experiment
comprises only of the materials, reactants, products and techniques used at the
experiment and nothing more. The objectives for this experiment are 1.) to
synthesize isoamyl alchohol to produce isoamyl acetate 2.) to calculate its % yield
3.) to learn how to use reflux technique and 4.) to learn the technique for
extraction,
washing
,
drying.
II. Methodology
First thing first, we set up for reflux and got the materials needed for it. The
materials are reaction flask, boiling chips, condenser, rubber tubing, water pump,
buret clamp, water bath (75 Celsius 80 Celsius), tripod, wire gauze, iron stand,
thermometer.
Then we got acetic anhydride C4H603 (5.2 mL) mixed with
concentrated sulfuric acid H2S4 (5 drops), it will serve as an acid catalyst, in a test
tube and got isoamyl alchol C5H12O (5.0 mL) in a separate test tube. Then we
mixed the two together and put it inside a beaker (250ml) with full of crushed ice
for cooling and constant temperature. After it is done, we transferred the
substance in a reaction flask and add 3 boiling chips inside. We refluxed the
substance, heated it by Bunsen burner at a constant 75 Celsius 80 Celsius for
30 minutes. The reason for it was to keep the reaction at a reflux temperature for
example, the boiling point of the solvent, and at the same time preventing it from
evaporating.*
After refluxing, we transferred the substance without the boiling chips in a 50 mL
beaker with crushed ice for washing with water and also for cooling it. After that,
we transferred the substance in a seperatory funnel fixed with an iron stand and
ring. But before we putted it inside the seperatory funnel we must close the valve
(horizontally) and open up the cover above. There must be one opening for the
gases to release. And then we added 15 mL saturated sodium bicarbonate
(NaHCO3). To swirl effectively until two layers separate, we used the bottom of the
seperatory funnel because its base is bigger and easier to swirl. Using common
sense, we closed the cover and opened up the valve for contents not to drop. After
swirling, we putted it back downside and discarded the lower layer because it is
not acetyl actetate, keeping only the upper layer. Then we added 15 mL of
saturated sodium chloride (NaCl) to remove the unreacted starting materials, side-

products and most water. As we did before, we swirled and allowed the two layers
to separate. We discarded again the lower layer and kept the upper layer.
After that, we drained the substance in a clean, dry 50 mL beaker and added
spatula anhydrous sodium sulfate (Na2S04) serving as the drying agent and to
remove remaining water in the solution. We swirled it efficiently and slowly
decanted, or poured gradually without disturbing the sediment into the preweighed vial. Finally, we weighed the vial with isoamyl acetate and computed for
its percent yield.
*At the end of reflux period, the reaction mixture will contain unreacted acetic acid,
sulfuric acid, water, unreacted isopentyl alcohol, and some unwated by-products.
Isopentyl acetate is quite insoluble in water, whereas both acetic acid and sulfuric
acid are water soluble and acidic. This makes it easy to separate the two acids
from the product by washing the reaction mixture with water and then with
aqueous sodium bicarbonate.
Example of a reflux set-up

III. Results

Example of a seperatory funnel

Table 1 Percentage yield of Isoamyl Acetate per group

Group No.
1
2*
3
4
5
6
7
8
9
10
11
12

% Yield
48.64
37.04
51.97
50.08
60.67
43.33
63.28
54.03
59.94
76.
70.25

IV. Discussion
The esterification reaction is reversible, and it has an equilibrium constant of
approximately 4.2. If you were to start with equimolar amounts of acetic acid and
isoamyl alcohol, only about two-thirds of each reactant would be converted to
isoamyl acetate by the time equilibrium was reached. Your highest attainable yield
in that case would be only 67% of the theoretical value. Thus, despite having a
high atom economy, the reaction efficiency of the synthesis could be rather low. To
increase the reaction efficiency, you will apply Le Chatelier's principle by using a
100% excess of acetic acid- the less expensive reactant- to shift the equilibrium
toward the products. Even then, the reaction will not be complete at equilibrium,
so the reaction mixture will contain some isoamyl alcohol as well as excess acetic
acid. The key concept here is that for a reaction at equilibrium adding more of a
reactant or removing a product will shift the equilibrium to favor the products.
V. Conclusion
Based on the results obtained from the experiment, we were able to get the
percent yield of isoamyl acetate. And through the procedure of the experiment, we
were able to learn how to use reflux technique and learn extraction, washing and
drying of isoamyl acetate. If you look at the percent yield of the asterisked group,
the percent yield is smaller than the highest attainable 67% yield of the theoretical
value. It means there is an error to the reacting side. We were not able to reflux
properly the isoamyl alcohol for 30 minutes but instead only 15 minutes because
we had less available time and had to compress time to complete the procedure of
the experiment. Next time we will be more prepared and quick as a group to be
able to finish quickly and accurately all the experiments and to produce a better
result.
References

IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected
version: (2006) "esters
Lehman, John W. (2009). Operational organic chemistry : a problem-solving approach to the
laboratory course. 4th Edition. Upper Saddle River, N.J. : Pearson Prentice Hall
https://www.boundless.com/chemistry/textbooks/boundless-chemistry-textbook/organic-chemistry23/functional-group-names-properties-and-reactions-166/esters-642-7517/
Appendix
isoamyl alcohol + acetic anhydride isoamyl acetate + acetic acid
1. balanced the equation
C5H12O + C4H6O3 C7H14O2 + C2H4O2
2. moles of isoamyl alcohol + acetic anhydride
4.064g C5H12O x 1mol C5H12O/88.2g C5H12O = 0.0458 moles C5H12O
5.6g C4H6O3 x 1mol C4H6O3/102.1g C4H6O3 = 0.0548 moles C4H6O3
3. Stoichiometric ratio
1mol C5H12O: 1mol C4H6O3: 1mol C7H14O2
4. Limiting reagent = isoamyl alcohol or C5H12O
0.0458 moles C5H12O x 1mol C7H14O2/1mol C5H12O x 130.2g C7H14O2/1 mol = 5.96g
0.0548 moles C4H6O3 x 1mol C7H14O2/1mol C4H6O3 x 130.2g C7H14O2/1 mole = 7.13g
5. Moles of isoamyl acetate
5.96g C7H14O2 x 1mol/130.2g C7H14O2 = 0.0457 moles C7H14O2
6. Grams of isoamyl acetate
5.96g C7H14O2
7. Volume of isoamyl acetate
0.867 g/ml 5.96 g/mol = 6.8036 ml C7H14O2
8. % Yield of isoamyl acetate = 23.9649g 21.7573g = 2.2076g/5.96g x 100 = 37.04%
(vial with isoamyl acetate) (pre-weighed vial)