#13 Dela Cruz

Group 5 #14 Egenias

#15 Garcia
2CHEM1
04 November 2019
C401L STUDENT RESEARCH PROPOSAL ABRIDGED FORM 2019

A. Proposal Title. Synthesis of dimethyl 2-phenylcyclopropane-1,1-dicarboxylate

B. Research Objective(s).
The main objective of this proposal is to synthesize the octyl acetate. The specific objectives are to calculate the
percentage yield of octyl acetate, to characterize the octyl acetate, and to determine its efficiency.

C. Literature Review. Esters are normally found in a variety of fruits and flowers. One property of ester is their
distinct fragrance. Esters with low molecular weights are usually found in some essential oils and perfumes
(Mott, n.d.). They are derived by an acid-catalyzed reaction of an alcohol and a carboxylic acid in the presence of
a dehydrating substance, and this process is known as Fischer esterification (Solomons, 1997). The general
structure for an ester is illustrated as follows.

Figure 1: General structure for Ester

There are different esters that can be produced with an alcohol with different kinds of acids. Octanol is an
example of alcohol and if mixed with acetic acid, or ethanoic acid, octyl acetate is formed.

Figure 2: Esterification reaction of octyl acetate

Octyl acetate is an ester commonly found in alcoholic beverages. It is also present in citrus peel oils, wheat
bread, cheddar cheese, banana, and sour cherry. It is used as a flavour ingredient. It is also the basis for artificial
orange flavoring (Yannai, 2003).

In the esterification reaction of octyl acetate, the equilibrium for the forward and reverse reaction for the
alcohol and carboxylic acid favors the reactants. Catalysts are used to increase the reaction rate and water is
removed on the product side to shift the equilibrium towards the products. Dehydrating substances is used to
remove the water and this may improve the % yield for ester.

D. Research Methods.

This procedure was based from the synthesis of ester by Solano from California State University. In a 25-mL or
50-mL round bottom flask, (45-mmol) alcohol and (12-mmol) of carboxylic acid will be added. A magnetic stirrer
will then be added to the flask containing the alcohol and the carboxylic acid. Dropwise addition of 1-mL of
concentrated sulfuric acid will be added to the flask. Afterwards, an apparatus for reflux using a water-cooled
condenser will be prepared. A drying tube will be used to prevent any additional water to be involved in the
reaction. The rheostat will be turned and the heat will be adjusted until the mixture boils gently. This heating
process under reflux will be continued for at least sixty (60) minutes. The mixture will be cooled afterwards.
Once the reaction will be completed, the cooled mixture will be transferred to a separatory funnel. Addition of
15-mL of ice cold water will be done and the phases will be mixed by gentle shaking and venting. The phases will
separate and the aqueous layer will be discarded afterwards. The organic layer will be washed by adding 5-mL of
5% aq. sodium bicarbonate and shaking it afterwards. The aqueous layer will be discarded once again. Another
washing will be done but using a 5-mL of saturated aqueous sodium chloride. The final aqueous layer will be
discarded. Afterwards, the mixture will be transferred to an erlenmeyer flask or beaker. A scoop of anhydrous
sodium sulfate will be added to the organic layer containing the cure octyl acetate. The mixture will then be
covered and let it stand for about 15 minutes. If the liquid is dry, the sodium sulfate will be loose. Otherwise,
another portion of anhydrous sodium sulfate will be added to complete the drying process of the crude. The
sodium sulfate will then be filtered and the remaining crude octyl acetate will be purified using microscale
fractional distillation using an apparatus with a Hickman still. The purified ester will be weighed and the
percentage yield will be computed afterwards.

Infrared Spectroscopy will be conducted to the yielded product. Infrared spectroscopy is an analysis of infrared
light interacting with the molecules. It is used to determine the functional groups present in a compound. The
 #13 Dela Cruz
Group 5 #14 Egenias
#15 Garcia
2CHEM1
04 November 2019
2019
FTIR spectra from the product will then be compared to the IR spectra of octyl acetate to verify the identity of
the product. Attached below is an FTIR spectra of octyl acetate from Bio-Rad Laboratories.

Figure 3: FTIR Spectra of Octyl acetate

Copyright © 1980, 1981-2018 Bio-Rad Laboratories, Inc. All Rights Reserved.

E. Timetable.
S Target Tasks Activity by Weeks
t Oct Nov Dec
a
g
e 1 2 3 4 1 2 3 4 1 2
s
1 Literature search
2 Proposal writing/ Teacher
consultations
3 Experimental
4 Summary report writing
5 Project presentation

F. References.
Department of Chemistry & Biochemistry. (2015). Lab 12: Synthesis of ester. California State University, Bakersfield
Lampkowski, J. S., Bass, W., Nimmo, Z., & Young, D. D. (2015). Microwave-Assisted Esterifications: An Unknowns
Experiment Designed for an Undergraduate Organic Chemistry Laboratory. World Journal of Chemical
Education, 3(5), 111-114.
Mott, V. (n.d.). Introduction to Chemistry. Retrieved from
https://courses.lumenlearning.com/introchem/chapter/esters/.
Solomons, T. W. (1997). Fundamentals of organic chemistry.
Subramanian, A. (2016). Analytical methods: Infrared spectroscopy in dairy analysis. Retrieved from
https://www.sciencedirect.com/topics/food-science/infrared-spectroscopy
Yannai, S. (Ed.). (2003). Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Crc Press.