Solomon, Joshua Daniel F.

Date Performed: Feb 18, 2016

Group No. 11

Date Submitted: Feb 26, 2016

Experiment No. 2
Preparation of Fruit Flavors

Introduction
In this experiment, the group should be able to achieve the following objectives:
(1) prepare the assigned ester via Fischer reaction and (2) to calculate its percent yield.
Esters are chemical compounds derived from an acid (organic or inorganic) in
which at least one -OH (hydroxyl) group is replaced by an -O-alkyl (alkoxy) group.
Usually, esters are derived from a carboxylic acid and an alcohol. Glycerides, which
are fatty acid esters of glycerol, are important esters in biology, being one of the main
classes of lipids, and making up the bulk of animal fats and vegetable oils. Esters with
low molecular weight are commonly used as fragrances and found in essential
oils and pheromones. Esters are responsible for the aroma of many fruits including
apples, durians, pears, bananas, pineapples, oranges and strawberries.
Esterification is the general name for a chemical reaction in which two reactants
(typically an alcohol and an acid) form an ester as the reaction product. Esters are
common in organic chemistry and biological materials, and often have a characteristic
pleasant, fruity odor. This leads to their extensive use in the fragrance and flavor
industry.
Organic reactions run faster at higher temperatures and slower at lower
temperatures. Many reactions commonly run in an organic laboratory need to be heated
in order to proceed at a satisfactory rate. The most convenient way to heat a reaction is
by boiling it in a solvent in a conical vial or round bottom flask. It is easy to observe
whether or not a liquid is boiling, and because of the laws of thermodynamics, once

boiling begins the temperature cannot rise any higher. To control the temperature of the
reaction, simply choose a solvent with a boiling point at this temperature.
To prevent the solvent from boiling away, a reflux condenser is used. This is a
glass column with a second column surrounding it through which cool water flows. As
vapor from the boiling solvent rises into inside column of the reflux condenser, it is
cooled by the jacket of water on the outside and condenses. It then falls back into the
solution. In this way, you can maintain a reaction at the boiling point of the solvent
indefinitely, as long as the water in the reflux condenser is cool enough to condense the
entire vapor.
Extraction is a very common laboratory procedure used when isolating or
purifying a product. Organic chemistry employs solid-liquid, liquid-liquid, and acid-base
extractions. The following applies to liquid-liquid extractions, which will be used in this
course. It is very common for organic products synthesized in a reaction to be purified
by liquid-liquid extraction. A separatory funnel is used for this process. In this procedure,
the organic product is isolated from inorganic substances. The organic product will be
soluble in an organic solvent (organic layer) while the inorganic substances will be
soluble in water (aqueous layer).
Although the criteria state that the organic solvent chosen should not be miscible
with water, some solvents dissolve a small amount. Thus, water must be removed
before separating the organic product from the organic solvent or else the product will
be contaminated with water. A drying agent must be used. There are a number of drying
agents available to the organic chemist: we will be using sodium sulfate and magnesium
sulfate in this course. Placing the organic solvent containing the dissolved product in
contact with the chosen drying agent will allow the agent to absorb any dissolved water.
The agent can then be removed from the solvent and then the product can be isolated.

Methodology

All equipment and glass wares that are needed in order to perform the
esterification and extraction of organic product from inorganic substances. The
apparatus for refluxing and extraction were assembled.

2.0 mL of the octyl alcohol was prepared in a test tube A. 2.0 mL of acetic
anhydride with 5 drops of concentrated sulfuric acid was prepared in test tube B. The
two test tubes were placed in an ice-water bath and slowly mix the contents of test
tube B to A (the reaction is violently exothermic). The solution with boiling chips was
placed in the round-bottom flask for reflux and heated in a specific temperature for
given period of time. It was transferred into a beaker and cooled for minutes in icewater bath. After being cooled, it was transferred into a separatory funnel with 15mL of
Na2HCO3 solution. Two layers can be seen clearly after the bubbles were gone. Gently,
it was covered and swirled to avoid emulsion, and also to separate the two layers. The
lower layer was extracted and disregarded. Another 15 mL of Na 2HCO3 solution was
added for another extraction. 15 mL of NaCl was used to the final extraction of the
organic layer. The organic layer was placed in a beaker with anhydrous Na 2SO4 to
separate the water contents remaining in the organic layer by decanting it into a dry,
clean test tube.

The final product weighed in an analytic balance and recorded the mass. The
extract was stored in the locker for the next experiment. The actual, theoretical and
percent yields were calculated. The following formulas were used to determine the
actual, theoretical and percent yields:

Theoretical Yield =

g C8 H 18 O

mol C8 H 18 O mol C10 H 20 O2

g C 10 H 20 O2

g C 8 H 18 O
mol C 8 H 18 O mol C 10 H 20 O 2

Actual Yield = M (beaker + empty test tube) M (beaker + test tube with product)
Percent Yield (%) =

Actual Yield
100
( Theoretical
Yield )

Figure 1: Reflux Actual Set-up

Figure 2: Extraction Actual Set-up

Results and Discussion

Mass (beaker + empty test tube) =

131.2320 grams

Mass (beaker + test tube with product) =

132.3180 grams

Actual Yield =

1.086 grams

Flavorings

Octyl Alcohol

Acetic Anhydride

Orange essence

2.5 mL

2.0 mL

(Octyl Acetate)

(C8H18O)

(C4H6O3)

Table 1: Volumes of reactants

Reagents

Density

Molecular Weight

Octyl alcohol

0.824 g/mL

130.26 g/mol

Acetic Anhydride

1.0820 g/mL

102.1 g/mol

Octyl Acetate (product)

0.863 g/mL

172.3 g/mol

Table 2: Density and Molecular weight of the Reagents and Product

Balanced chemical equation for octyl acetate,

2C8H18O + C4H6O3 ----> 2C10H20O2 + H2O

As shown above, the percent yield can be calculated. The students found first the
actual and theoretical yield of the product. The equations and given data above will give
the value of the grams of the reagents. Knowing the limiting reagent in the chemical
reaction will derive you to get the theoretical yield of the product, octyl acetate. The
students got the actual value from subtracting the mass of the beaker with test tube
containing the product to the mass of the beaker with an empty test tube. And by

dividing the actual yield to the theoretical yield multiply by 100 percent, the percent will
be obtained.
Calculations for the Percent yield:
Grams of Octyl Alcohol,
2.5 mL C 8 H 18 O

0.824 g C 8 H 18 O
=2.06 g C 8 H 18 O
ml

Grams of Acetic Anhydride,

2.0 mL C 4 H 6 O3

1.0820 g C 4 H 6 O3
=2.164 g C 4 H 6 O3
ml

*Octyl Alcohol is the limiting reactant and the Acetic Anhydride is the excess
reactant.

Theoretical Yield

= C H O mol C 8 H 18 O mol C 10 H 20 O2 g C10 H 20 O2

8
18
g C8 H 18 O
mol C 8 H 18 O mol C10 H 20 O2
=

2.06 gC 8 H 18 O

Percent Yield =

1 mol C8 H 18 O
2mol C 10 H 20 O2 172.3 g C 10 H 20 O 2

130.26 g C 8 H 18 O 2 mol C 8 H 18 O
1 mol C10 H 20 O2

2.725 g C 10 H 20 O 2

Actual Yield
100
( Theoretical
Yield )
g
100
( 1.086
2.725 g )

= 39.85%

Figure 4: The weight of the Mass

(beaker + empty test tube)

Figure 5: The weight of Mass

(beaker + test tube with product)

Conclusion
Throughout the experiment, the students completely prepared the assigned ester
via Fischer reaction. Using the octyl alcohol and acetic anhydride with sulfuric acid as
the acid catalyst, the ester in octyl acetate will be obtained. To calculate the percent
yield, the students found first the actual and theoretical yield of the product. The
calculated percent yield the students got was low. There were some reasons why the
calculated percent yield was low. The refluxing of the mixture or solution could be one of
possible reason because not all the vapor condensed when the temperature reached it
80 degree Celsius and stay for specific period of time. The transferring of the mixture
could also be a reason because not all the solution or reagents were transferred into
another container. Another reason was the extraction of organic layer because not all of
the solutions reacted on the sodium bicarbonate and NaCl. Also, some of the solutions
remained in the beaker with anhydrous sodium or magnesium sulfate.

References

1 Ester.
(n.d.).
Retrieved
February
25,
2016,
from
https://en.wikipedia.org/wiki/Ester
2 Chem 211 - Techniques. (n.d.). Retrieved February 25, 2016, from
http://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appen
dix/Techniques/Extraction/extraction_n.html
3 Refluxing A Reaction. (n.d.). Retrieved February 25, 2016, from
http://cactus.dixie.edu/smblack/chemlabs/refluxing_a_reaction.pdf