Experiment # 14

Experiment #14: Preparation of Banana Oil and

Characterization using IR Spectroscopy
One of the simpler organic reactions that can be carried out is the formation of an
ester from an acid and an alcohol. This reaction proceeds as follows:
O O
+ HO R' + H2O
R OH R OR'
an acid an alcohol an ester

In the equation above, R and R’ are H atoms or organic fragments like CH3, C2H5, or
more complex aromatic groups. There are many known esters in organic chemistry that
can be synthesized from organic acids and alcohols. The driving force for the reaction is
generally not very great, resulting in an equilibrium mixture of the formed ester, water,
acid, and alcohol as will be demonstrated below.

Esters impart a pleasant odor and are often responsible for the flavor and scent of
fruits and flowers. The total essence or taste is usually due to a mixture of organic
compounds, and thus, artificial flavorings are formulated by mixing a variety of synthetic
alcohols, esters, aldehydes, and ketones. Banana oil, or isoamyl acetate, is produced by
the reaction of acetic acid and isoamyl alcohol:

O O
+ + H2O
H3C OH OH H3C O
Acetic Acid Isoamyl alcohol Isoamyl acetate Water

During the first portion of this experiment, you and your lab partner will synthesize
banana oil, assemble a distillation apparatus in order to purify your ester, and then
characterize your isolated product via infrared (IR) spectroscopy.

IR spectroscopy allows a chemist to deduce the structure of a molecule. In this

particular experiment, we will compare the IR spectrum of your product with purified
isoamyl acetate as well as isoamyl alcohol to determine the success of your distillation
(purification). In infrared spectroscopy, each type of bond in a molecule absorbs a
characteristic frequency of IR light as it vibrates, and these frequencies can often be used
to determine which types of bonds the molecule actually contains. These vibrations fall
into several different categories as shown for a generic three atom system:

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 Experiment # 14

Modes of vibration

Symmetric stretching Antisymmetric stretching Scissoring

The frequency of light that is absorbed is closely related to the strength of the bonds. An
analogy is that of the stretching of a spring. If we imagine each bond as a spring, the
frequency of vibration of a spring will be greater if the spring is stiffer. A stiffer spring is
equated with a stronger bond; a stronger bond vibrates at a higher frequency.

Recall that Planck’s equation relates the frequency, wavelength, and energy of
light:
∆E = hν = hc/λ

where “h” is Planck’s constant (6.626 x 10-34 J s) , “ν” is the frequency of light, “λ” is the
wavelength, and “c” is the speed of light (3.0 x 108 m/s). Also notice that:

ν = c/λ

In IR spectroscopy, wavelengths are measured in microns (µm), and frequency is

measured in cm-1 (called “wavenumbers”). Your measurements will be made in
wavenumbers. Note that wavenumbers (1/λ or cm-1) and frequency (ν) are directly
proportional. Some typical frequencies (in wavenumbers) for the stretching of common
types of bonds are listed below:

Alcohols R-OH 3200 - 3650 cm-1

Amines R2-NH 3300 - 3500 cm-1

Alkanes C H 2840 - 3000 cm-1

O O
Carbonyl group in aldehydes and ketones, C=O, 1690 - 1750 cm-1
R H R R'

Alkenes 1620 - 1680 cm-1

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 Experiment # 14

In general, the symmetric bond stretching frequencies are more clearly shown in
the IR spectrum and found in the 4000-1500 cm-1 region. The other types of vibrations,
antisymmetric stretches and scissorings, are generally seen in a complex region below
1500 cm-1 called the “fingerprint region.” However, since the IR spectrum of each
molecule should also be unique, the entire spectrum actually serves as a “fingerprint” of
the molecule. The spectrum can be used to identify the types of bonds in the molecule,
like the examples given above, or, if the spectrum of your compound matches that of a
known compound, you can conclude that your compound and the known are the same.
Consider the IR spectra shown below for both isoamyl alcohol and isoamyl acetate:

4000 3000 2000 1500 1000 500

-1
(cm )
Figure 1: IR spectrum of isoamyl alcohol

4000 3000 2000 1500 1000 500

(cm-1)
Figure 2: IR spectrum of isoamyl acetate

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 Experiment # 14

Identify the distinguishing features of each spectrum and compare the acquired spectrum
of your final product with these spectra.

Procedure

1. Obtain a 1000 mL beaker and add DI water to approximately half the beaker
along with 4 to 5 boiling chips. Support the beaker of water on a wire screen and
ring attached to a ring stand and bring the water to boil.

2. Now obtain a clean 250 mL Erlenmeyer flask. First add 24 mL of acetic acid,
making certain to record the actual volume used. While WORKING IN THE
HOOD, SLOWLY AND CAUTIOUSLY add 10 mL of concentrated sulfuric acid
to your Erlenmeyer flask and swirl to mix. Your mixture will become hot.
Finally, add 27 mL of isoamyl alcohol to your mixture, record the actual volume
used, and swirl.

3. Place the Erlenmeyer flask with the mixture carefully suspended in the boiling
water bath. Adjust the flame to allow the water to GENTLY boil. Keep the
Erlenmeyer flask in the boiling water bath for 25 minutes.

4. While your mixture is reacting and heating, place approximately 150 mL of DI

water in any clean beaker and add ice to devise an ice-water mixture. Pour 75
mL of this ice-water into a 250 mL beaker and save the rest for the washes with
the separatory funnel.

5. Once the mixture has reacted, carefully remove it from the boiling water bath and
pour it into the 250 mL beaker containing the 75 mL of ice-water. Obtain a
separatory funnel and check to ensure the stopcock is CLOSED. Pour your total
mixture into the separatory funnel. Use the plastic stopper provided by your
instructor to close the opening (top) of the separatory funnel.

6. Gently shake your funnel for a few seconds, carefully turn your funnel upside-
down by supporting the stopper with one hand, and slowly open the stopcock to
release any build-up of pressure. Be sure the stopcock is facing away from you
and others. Repeat this procedure until the internal pressure is minimal, and then
shake vigorously to ensure thorough contact of the two liquids.

7. Place the separatory funnel in a small ring held by a ringstand to allow the layers
to separate. Obtain a clean 400 mL beaker, remove the stopper, and open the
stopcock, thereby draining the bottom aqueous layer into the 400 mL beaker.
When collecting the bottom layer, close the stopcock just as the upper layer
enters the stopcock bore. USE CARE AS THE BOTTOM LAYER IS ACIDIC
AND MUST BE NEUTRALIZED AND DISCARDED ONCE COMPLETELY
COLLECTED.

8. Wash the solution twice more with 25 mL portions of your ice-water, and collect

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 Experiment # 14

the bottom layer in the 400 mL beaker as described in step 7. Once completed,
the collected bottom layer should be neutralized with sodium bicarbonate and can
then be safely discarded in a sink with running water.

9. Transfer the ester (top layer) to a clean, dry 100 mL beaker containing
approximately 2 grams of anhydrous sodium carbonate. Allow to stand with
occasional swirling for about 5 minutes to allow the sodium carbonate to
neutralize any traces of H2SO4 and absorb any water. Carbon dioxide evolution
indicates that acid is being neutralized.

10. Pour only the liquid through a funnel placed in the distillation flask. The solid
remains in the 100 mL beaker. Add 2 – 4 boiling chips to the distillation flask.
Assemble the distillation apparatus as shown below (Figure 3). Be sure all
connections are made with rubber stoppers and are tight to prevent vapor leakage.
Also be sure your apparatus is securely supported. Your lab instructor will check
your set-up before proceeding. At this point, you should clean, dry, and weigh a
100 mL beaker for use in step 11.

Figure 3: Distillation setup

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 Experiment # 14

11. After the distillation flask is attached to the condenser, increase the voltage to
bring the liquid to a boil, and collect any condensed liquid (i.e. water) in a waste
beaker. Adjust the voltage so that the temperature gradually rises, the liquid
vaporizes, then condenses, and ultimately drips from the condenser at a rate of 1 –
2 drops per second. Once the temperature reaches 135 ºC, carefully maintain this
temperature by adjusting the voltage accordingly and begin collecting your
product in the previously weighed (and recorded) 100 mL beaker. Continue to
collect your product until the liquid in the distillation flask almost completely
disappears; at this point, IMMEDIATELY LOWER THE HEATING MANTLE
away from the distillation flask.

12. Weigh and record the mass of the beaker and ester. Also weigh and record the
mass of a clean, dry 10 mL graduated cylinder. Pour about 10 mL of the ester
into the cylinder, weigh and record its mass, and record the actual volume of the
ester in the graduated cylinder.

13. Pour the ester and any other distillation products in the properly labeled waste
bottle; DO NOT POUR ANY CHEMICALS DOWN THE SINK. Properly clean
and return all equipment. Be careful when dismantling your distillation apparatus
as the glassware is expensive. Wash this glassware with warm water and soap.
Rinse 3 times with DI water and then with acetone.

14. Once you have isolated your final product via distillation, your instructor will
assist you in acquiring an IR spectrum of your potential banana oil. Make certain
to include the printout of your spectrum with this final report and clearly label
the appropriate characteristic peaks. Does your spectrum more closely resemble
isoamyl alcohol or isoamyl acetate? What other potential impurity might be
present in your sample?

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 Experiment # 14

Data Analysis and Calculations

O O
+ + H2O
H3C OH OH H3C O
Acetic Acid Isoamyl alcohol Isoamyl acetate Water
MW ________ MW ________ MW ________

Density ________ Density ________ Density ________

Volume ________ Volume ________

(~ 24 mL) (~ 27 mL)

Mass of clean, dry 100 mL beaker ______________________

Mass of 100 mL beaker plus ester ______________________

Mass of ester (actual yield) ______________________

Mass of clean, dry 10 mL graduated cylinder ______________________

Mass of graduated cylinder plus ester ______________________

Volume of ester in graduated cylinder ______________________

Density of ester ______________________

SHOW CALCULATION:

Theoretical yield of ester ______________________

SHOW CALCULATION:

Percent Yield of ester ______________________

SHOW CALCULATION:

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 Experiment # 14

Post-lab Questions

1. As in many organic reactions, the synthesis of banana oil is one example of an

equilibrium reaction. Does your data support the presence of an equilibrium
mixture of reactants/products? Briefly explain why or why not.

2. Discuss the purity of your final product. How pure (or impure) is your banana
oil? Comment on how your IR spectrum parallels the spectrum of pure isoamyl
acetate, making certain to LABEL and discuss all characteristic absorption peaks.
Does your spectrum more closely resemble isoamyl acetate or isoamyl alcohol?
Briefly explain. What other potential impurity may be present in your sample?
You should turn in the labeled IR spectrum of your product with this report.

3. During the experiment, the procedure directs the student to wash the reaction
solution three times with water while in the separatory funnel. What was the
purpose of this step?

4. Why is sulfuric acid NOT included in the balanced chemical equation for this
organic reaction?

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