Name: Christian Job Oliver M. Mungcal Instructor: Engr.

Aldrin Lorrenz Chan

Section: 2CHEA Date Experiment Performed: Aug. 31, 2019

Group No.: 8 Date Report Submitted: Sept. 7, 2019

Experiment 2: Preparation of Synthetic Fruit Flavors

ABSTRACT

Ester is functional group derived from carboxylic acid and alcohol wherein -OH group is being
replaced by an -O group in its structure. It plays a huge role in both living world and industries especially
in food industry wherein fruit flavors are being featured. In this experiment, the ester was extracted from
the solution containing 2.5mL alcohol and 4mL acetic anhydride thru the refluxing and extracting.
Refluxing the carboxylic acid and the alcohol is a type of esterification known as Fischer Esterification or
Fischer-Speier Esterification but in this experiment, the esterification was modified by using acetic acid
instead of carboxylic acid. The ester formed is propyl acetate that has an odor of pear. The product was
obtained through refluxing and extraction and weighed 3.67g. Upon comparison between the theoretical
amount of the product and its actual amount that was obtained in this experiment, the % yield was 107.56%.

INTRODUCTION

According to Dr. Robertson, D. (2012), esterification is a straightforward reaction that utilizes

several key techniques in synthetic organic chemistry. A common one, known as the Fischer Esterification
reaction, involves the strong acid-catalyzed reaction between a carboxylic acid and an alcohol that yields
an ester and water. Acetic anhydride can also be use instead of carboxylic acid to make the reaction faster
and irreversible. In this experiment, an ester propyl acetate or propyl ethanoate from the pear was attained
via modified Fischer esterification reaction from the reaction of acetic anhydride and n-propanol.

H+ (Cat)

Acetic acid side

Acetic anhydride N-propanol Propyl acetate product
Figure 1. The modified Fischer esterification reaction of acetic anhydride and n-propanol
 Two processes will be done after the synthesis, refluxing and extracting. Refluxing is the process
of increasing the temperature of the reaction mixture in a vessel or pipe called condenser. A high
temperature result to an increase in the rate of reaction. As the reactants start to vaporize from the mixture,
they also condense back into the solution because it is being surrounded by the cooling water connected
through the condenser.

Extracting is one of the separating processes that involves two immiscible liquid phases-, the
solvent and solute phases - where the solvent phase extracts the solute from the other liquid phase. In the
experiment, the ester will be extracted from the product by adding an aqueous substance, NaHCO3 and
NaCl separately. Since ester has low solubility in water, the ester reports to the organic layer, while water-
soluble components separate to the aqueous layer. The excess reactants which are alcohol, sulfuric acid,
acetic anhydride and most of the water from the product will be mixed in the aqueous layer, thus purifying
the ester that is being catalyzed by NaHCO3 and NaCl.

The main objective of the experiment is to acquire the ester from the mixture of acetic acid and
alcohol thru synthesizing it by using the process of esterification. Then purify the ester that obtained through
the process of extraction and determine its percentage yield so we can be able to know if there are some
impurities or if the reactant was totally converted into product in chemical reaction.

MATERIALS AND METHODOLOGY

The substances that used in this experiment are: n-propyl, acetic anhydride, concentrated H2SO4,
saturated NaHCO3 solution, saturated NaCl solution, anhydrous Na2SO4, and ice cubes. The materials used
in this experiment are: test tubes, dropper, 250-mL beaker, spatula, Bunsen burner, thermometer, distilling
flask, condenser, rubber tubing, wire gauze, iron stand, iron ring, grease, boiling chips and separatory
funnel.

Reflux set-up was made first by putting iron stand and iron ring together, and then the Bunsen
burner, wire gauze, and condenser were placed accordingly. Water source was checked and one rubber
tubing was connected from the water source to the condenser and the other rubber tubing was connected
from the condenser to the nearest drain. A 250-mL beaker was placed above the tripod containing 150mL
of water.

A 2.5mL of n-propanol was placed in a test tube labeled A and 4mL of acetic anhydride was placed
in another test tube labeled B. Then both test tubes were placed in an ice-water bath for 5 minutes.
Concentrated H2SO4 was added in test tube B and proper mixing was induced while in an ice-water bath.
After 5 minutes, the contents of test tube B were transferred slowly in dropwise manner into test tube A.
Water in the reflux set-up was heated to 80oC. The test tube containing the mixture of A and B was
transferred in a flask and 5 pieces of boiling chips was added into it. The flask was immersed in the 250-
mL beaker, and the condenser was attached above of it. The flask was heated for 15 minutes at a constant
temperature (80oC). After 15 minutes of heating, the flask was removed from the set-up and cooled in a
small beaker containing a cube of ice in 2 minutes.

After 2 minutes, the extraction started by transferring the mixture inside a separatory funnel and 15
mL of saturated NaHCO3 was also added into it. The funnel was then gently swirled and inverted to release
the gas through the stopcock, thus decreasing the gas-pressure build up. The cap of the condenser was
detached and the lower layer was removed. Extraction was repeated with another 15 mL of NaHCO3. The
tea extract was then extracted with 15 mL of NaCl.

After the extraction, the remaining mixture in the separatory funnel was transfer to a clean beaker
containing anhydrous Na2SO4 and was swirled gently. The beaker’s weight was measured and it was
transferred in a test tube. The product was sealed and kept inside the cabinet.

Figure 2. The Reflux set-up diagram. Figure 3. Separatory Funnel diagram

RESULTS

Table 1. Weight of the product

Weight of the empty Erlenmeyer Flask 171.64 g

Weight of flask with product 175.31 g

Weight of the product 3.67 g

After weighing the flask with product, the value of it was subtracted to the value of weight of the
empty Erlenmeyer flask to get the weight of the product which is 3.67 g.

Table 2. Physical properties of the product

State Liquid
Color Colorless
Odor Strong acetone smell, pear
Other observations None

C4H8O3 + C3H8O → C5H10O2 + C2H4O2

Equation 1. The chemical equation after refluxing.

Table 3. Computations for the limiting and excess reactant in the reaction.

Chemical Compound Chemical Formula Molecular Weight Density

Acetic Anhydride C4H8O3 104.1 g/mol 1.08 g/mL Excess Reagent
N-propanol C3H8O 60.09 g/mol 0.803 g/mL Limiting Reagent
Propyl Acetate C5H10O2 102.131 g/mol 0.888 g/mL Product
Acetic Acid C2H4O2 60.052 g/mol 1.05 g/mL Side product
DISCUSSION

The amount of ester which is propyl acetate or C5H10O2 being yield is 3.412g. For the percentage
yield is 107% based on the actual yield which is the weight of the product, 3.67g and the theoretical yield
which is 3.412g.

Refluxing the mixture in this experiment is very important because we can be able to control the
temperature in the solution since the mixture has a low boiling point, it will vaporize immediately if exposed
to high temperature. The reflux set-up was necessary so that when the reagent was vaporized, it will just
drip back to the solution, preventing it from escaping as vapor because it was immediately being cool down
by the water from the condenser.

During the extraction, the saturated NaCl was used instead of plain distilled water because the
organic layer that formed already has a water in its content so if plain distilled water was used, the organic
layer’s volume will just increase because there would be no extraction. After the extraction, the final product
must be dried because there is still some H2O in its content so it was necessary to add the anhydrous Na2SO4,
a dehydrating agent, to remove the water in the product. While doing so, we can totally attain a pure ester
in the product but since the percentage yield was too high, it was observed that there are still impurities left
in the solution. The impurities were not able to taken out fully by the dehydrating agent. It can be suggested
that a huge amount of H2O was still in the product.

To further understand the concept of refluxing and extracting, there are some commercially
available products that can be separated by the extraction which is coffee and tea in which the caffeine in
its content is being isolated from a solid mixture by using water as a solvent in extracting.

CONCLUSION AND RECOMMENDATION

The ester formed which is propyl acetate is a colorless liquid and has an odor pear and strong
acetone which can be used as fragrance and flavor additives. The propyl acetate was also formed because
of the reaction between the acetic anhydride and n-propanol with H2SO4 as catalyst.

In this experiment, the ester was synthesized thru Fischer esterification reaction wherein acetic
anhydride and n-propanol was catalyzed under high temperature. The ester obtained was purified using
NaHCO3 and NaCl through the process of extraction.

During the experiment, the final weight of the product that was obtained is 3.67g which is higher
than the theoretical yield, 3.412g thus, a high percentage yield was attained which is 107.56%. The final
product still has some impurities and during the extraction, the ester was not able to fully purify as there
are still some excess of alcohol, acetic anhydride, and sulfuric acid. The possible indicator that lead into
this is the

To further improve the yield and have an accurate and precise data, it has been suggested that to
continue in practicing good and clean experiment to lessen the % yield as it can be led to human error and
other types of errors in such doing an experiment that has a reflux and extraction set-up.

REFERENCE

Robertson D. (2012, November). Fischer Esterification: Preparation of Isopentyl Acetate

(Isoamyl Acetate). Retrieved from: http://home.miracosta.edu/dlr/210exp7.htm

Ester. (n.d.). Retrieved from: https://www.ausetute.com.au/esters.html

Chemistry LibreText. (n.d.). Theoretical Yield and Percent Yield. Retrieved from:
https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/Book%3A_Introductory_Chemistry_(C
K-12)/12%3A_Stoichiometry/12.9%3A_Theoretical_Yield_and_Percent_Yield

Synthesis of an Ester: Fischer Esterification. (n.d.). Retrieved from:

https://academic.macewan.ca/saberim/263exp8.pdf

APPENDIX

Calculations in determining the limiting and the excess reactant in the reaction below

1.08𝑔 𝑚𝑜𝑙 𝑚𝑜𝑙 𝑜𝑓 𝑛 − 𝑝𝑟𝑜𝑝𝑎𝑛𝑜𝑙

4𝑚𝐿 𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒 𝑥 𝑥 𝑥
𝑚𝐿 102.09𝑔 𝑚𝑜𝑙 𝑜𝑓 𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒
= 0.0423 𝑚𝑜𝑙 𝑛 − 𝑝𝑟𝑜𝑝𝑎𝑛𝑜𝑙

0.803𝑔 𝑚𝑜𝑙 𝑚𝑜𝑙 𝑜𝑓 𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒

2.5𝑚𝐿 𝑛 − 𝑝𝑟𝑜𝑝𝑎𝑛𝑜𝑙 𝑥 𝑥 𝑥
𝑚𝐿 60.09𝑔 𝑚𝑜𝑙 𝑜𝑓 𝑛 − 𝑝𝑟𝑜𝑝𝑎𝑛𝑜𝑙
= 0.0334 𝑚𝑜𝑙 𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒

3.67𝑔
% 𝑦𝑖𝑒𝑙𝑑 = 𝑥 100% = 107.56%
3.412𝑔