Experiment 6

Synthesis of Isoamyl Acetate (Banana Oil)

Joshell Mharielle C. Sion/ Group 4

October 17, 2019

1. Introduction

Esters have the structure of -COOR. Instead of the alcohol portion of the carboxylic acid (-COOH), there
is an ether portion. The low boiling, volatile esters are known for their "fruity" smell and flavor. They are used
in artificial flavorings. These are a class of compounds found widely in nature. The ester functional group
can be synthesized by many methods. The simplest approach is Fisher esterification. By this method, esters
are produced by refluxing a carboxylic acid and an alcohol in the presence of a concentrated acid catalyst.
To exploit Le Chatelier’s principle and shift the position of the equilibrium to the right we add an excessive of
one of the reactants to the reaction mixture. The general mechanism for the Fischer esterification is shown
in Figure 1.1 and Figure 1.2.

Figure 1.1 First Part of the mechanism on the Synthesis of Isoamyl Alcohol

The mechanism of the reaction of Acetic Acid and Isopentyl Alcohol with sulfuric acid starts with
deprotonation of sulfuric acid using the lone pair of the carbonyl oxygen. This is to make the sulfuric acid a
better electrophile. The isopentyl alcohol would make a nucleophilic attack with the protonated acetic acid to
create a tetrahedral intermediate. The remaining negatively charged ions from the sulfuric acid would
deprotonate the tetrahedral intermediate and reform the sulfuric acid catalyst.
 Figure 1.2 Second Part of the mechanism on the Synthesis of
Isoamyl Alcohol

The OH would protonate with sulfuric acid to form a good leaving group which would make water
(H2O) leave. The OH would reform to make a carbonyl group. The hydrogen on the carbonyl group would
create a positive charge. This would be deprotonated by the negative charged ions of sulfuric acid (HSO 4).
The final product of the reaction would be Isopentyl acetate, sulfuric acid catalyst and water.

For this experiment, the aim of the researcher are to synthesize Isoamyl acetate and to understand
the mechanism of preparing ester. These objectives will give the researchers a concise understanding on
the process of synthesizing

2. Materials and Methods

The set up for the Reflux of isoamyl acetate and sulfuric acid was shown in Figure 2.1. Ten (10)
millimeters of Isoamyl alcohol and 15 mL of acetic acid were added to a round bottom flask. Three(3)
millimeters of concentrated sulfuric acid (H2SO4) was added gradually with continuous shaking of the
solution. Boiling chips were added to easily observe the boiling process. The flask was placed back on the
set-up as shown in Figure 2.1. The solution was boiled and let it reflux for 60 minutes.

Figure 2.1 Reflux Set up

https://www.researchgate.net/publication/287346837/figure/fig2/AS:3
28154553045003@1455249550560/Schematic-of-reflux-setup.png
 After the reflux, the solution was cooled to room temperature which is about 30 0C. The extraction set
up (Figure 2.2) was prepared. The solution was placed inside the Separatory funnel with 27 millimeters of
deionized water. The mixture was shaken and settled to let the organic layer separate from the aqueous
layer. The bottom layer was extracted from the mixture. Twenty- five (25) millimeters of sodium bicarbonate
(NaHCO3) was added to the remaining organic mixture on the funnel. The process for extraction was
repeated until the pH of the solution reaches 8 or more.

Figure 2.2 Extraction Set up

http://umich.edu/~chemh215/W13HTML/SSG5/ssg5.6/sepfunnel.jpg

The final extracted organic phase was mixed with 25 millimeters of deionized water and 5 millimeters
of sodium chloride (NaCl). The aqueous layer of the mixture was extracted and discarded. The
remaining organic solution was transferred to a 50-mL beaker. Two (2) grams of magnesium sulfate
(MgSO4) and let the solution stand for 15 minutes.

Figure 2.3 Addition of MgSO4

 The final process of the experiment was distillation. The set up for distillation was shown in Figure
2.4. The solution was separated from the white residue and it was measured using the analytical balance.
The solution was transferred to a round bottom flask. Boiling chips were added to the solution. It was heated
until the mixture reaches the temperature of 134 0C to 143 0C. The banana oil recovered was distilled from
the solution and its mass was measured.

Figure 2.4 Simple Distillation Set up

http://jupiter.plymouth.edu/~wwf/distillation_files/image001.jpg

3. Results and Discussion

Table 1: The percentage recovery of the synthesis of Isoamyl Acetate

Weight of Crude product (grams) 4.29

Weight of pure product (grams) 5.27
Percentage Recovery 81.4

The first part of the synthesis of Isoamyl alcohol is the Fischer esterification. The researchers observe
that the solution produce heat when concentrated sulfuric acid was added. This shows that there was an
exothermic reaction taking place. When the mixture is refluxed, it produce an aroma of bananas. The next
process takes three extraction using 10% sodium bicarbonate to attain a pH level of 8. The solution
remains colorless throughout the process. The table above shows the initial mass of the pure product
before distillation attain from the reflux and extraction. The percentage recovery of the banana oil is 81.4%.
This is within the range of accepted percentage recovery for the synthesis of Isoamyl alcohol. The results
also shows the efficiency of this method in attaining banana oil from the synthesis of Isoamyl alcohol.
 4. Conclusion

The objectives of the experiment are to synthesize Isoamyl acetate and understand the mechanism
of preparing ester. Based on the results, the researcher was able to successfully attain these objectives. The
percentage recovery from distilling the pure product is 81.4%. This means that the process of synthesizing
Isoamyl acetate was performed effectively. However, there are sources of error that are significant to
consider. These errors might have influenced the direction of the results produced in this experiment. During
the addition of sodium bicarbonate, some of the mixture spilled while venting the separatory funnel to remove
the carbon dioxide. This incident might have decrease the yielded pure product.
To further improve this experiment, the researcher is suggesting to use nuclear magnetic resonance
spectroscopy (H NMR) to confirm the identity and purity of the final product. The researcher also recommends
to carefully perform each process in order to increase the percentage recovery.

5. References

Ashley, B. (2019). Sythesis of Isopentyl Acetone Banana Oil Lab Report. Retrieved 24 October 2019, from
https://www.studocu.com/en/document/university-of-minnesota-twin-cities/organic-
lab/practical/sythesis-of-isopentyl-acetone-banana-oil-lab-report/1036063/view

(2019). Retrieved 24 October 2019, from https://assets.thermofisher.com/TFS-Assets/CAD/Reference-

Materials/pS45-Fisher-Isoamyl-Acetate.pdf

Andre, D. (2007). Fischer Esterification: Preparation of Banana Oil. Retrieved from

http://d.web.umkc.edu/drewa/Chem322L/Handouts/Lab10HandoutFischerEsterificationOfBananaOil32
2L.pdf