Jiara Laine Montano

13 September 2016

Chem 26AA

30 September 2016
Experiment no. 5: Preparation of Benzyl Acetate

Data and Results

Data
Value
Weight of Vial
17.22 grams
Weight of Vial + Solution
20.64 grams
Weight of Solution
3.42 grams
Final Volume of Solution
3.7 cm3
Volume in Vial
3.3 cm3
Experimental Density
1.036 g/cm3
Theoretical Yield
11.023 mL
Actual Yield
3.7 mL
Percent Yield
33.57 %
Table 1.1 Experimental and derived data from the preparation of benzyl acetate
Test
Chromic Acid Test
Hydroxamic test
Carboxylic acid test
Table 2 Qualitative test results

Result
Positive
Negative
Negative

Discussion
This experiment aimed to synthesize benzyl acetate through Fischer Esterification. Fischer
esterification or Fischer-Speier esterification is a particular type of esterification reaction that
uses a carboxylic acid (i.e. acetic acid) and an alcohol (i.e. benzyl alcohol) in the presence of
an acid catalyst (i.e. sulfuric acid). Aside from this process, there are also other methods
available for the synthesis of esters. Alcohols can readily react with anhydrides and acid
chlorides. Although, these synthetic routes are also alternatively used, direct acylations of
alcohols with carboxylic acid is preferred over acylations with anhydrides and acid chlorides
due to the following reasons: acid anhydrides are less electrophilic than acyl chlorides
and only one acyl group is transferred per molecule of acid anhydride which leads to a
lower atom efficiency. Acid chlorides, on the other hand, are very reactive and highly
moisture sensitive. Reactions with this chemical frequently produces hydrogen chlorine
gas which in turn is a hazardous chemical that forms corrosive hydrochloric acid on
contact with water found in body tissue.
In this experiment, approximately 3.7 mL of benzyl acetate has been produced. However, to
ensure the purity of the product qualitative tests were performed to ascertain that that there is
an absence of acetic acid and benzyl alcohol in the solution as the absence of benzyl alcohol
and acetic acid are indicators of purity in this experiment. Moreover, the chromic acid test
was executed to ensure that the product is indeed benzyl acetate. Since the Hydroxamic acid
test and carboxylic tests had negative results it can be said that there are no benzyl
alcohol and acetic acid left in the solution. Furthermore, based on the positive test result

of the Chromic acid test and the odor (i.e. peachy smell) and appearance (i.e. clear
colorless liquid) of the product, the end product is reasonably a relatively pure benzyl
acetate solution.
However, note that the experimental density has a 1.30 % error with the literature value for
the density of benzyl acetate. This implies that there might be other impurities in the solution.
After the reflux reaction, the liquid in the round bottom flask had a yellow tinge and
had white precipitate in it which indicates formation of by-products (e.g. amine
derivatives) aside from benzyl acetate. These by-products can also act as impurities in
the final solution had the washings and decanting not done efficiently.
Similarly, the formation of by-products also affects the yield. These side reactions that
accompanied the main reaction of acetic acid and benzyl acetate would significantly
limit the percent yield of the product. Take note from the table that the percent yield is
33.57%. As one can see the actual yield is relatively low as compared to the theoretical yield
in Table 1.1. Also, note that Fischer esterification is an equilibrium process. Meaning, the
reaction does not go to a 100% completion because to some extent it the reverse
mechanism also occurs thus limiting the percent yield. Furthermore, once the number of
reactants left is very slim the chances of them colliding becomes remote thus the product
of this amount of reactant left is unable to contribute to the final amount of product.
Distilling the resulting mixture before decanting is not an efficient way to purify the
product because while the relative boiling point of acetic acid (i.e. 118 C) is lower
compared to the other two components of the reaction, that is, benzyl acetate (i.e.
212C) and benzyl alcohol (i.e. 205C), the relative boiling points of these two are quite
close. According to Guidote et al. the boiling points of the mixture must differ by at least
25 C and evidently benzyl alcohol and benzyl acetate only differ by 7 oC. Thus, after
distillation the receiving flask will contain a mixture of the benzyl acetate and benzyl
alcohol.
Conclusion
Through the esterification process of benzyl alcohol and acetic acid catalyzed by sulfuric
acid, approximately 3.7 mL of benzyl acetated has been produced. The purity of this
substance has then been successfully ensures by qualitative tests that indicated the absence of
benzyl alcohol and carboxylic acid. It has also been determined that the experimental density
is approximately 1.04 g/mL. As the production of benzyl acetate, relative purity via
qualitative tests, experimental density and percent yield has been determined and completed
it can be said that the objectives of the experiment has been met. However, although the
benzyl acetate has successfully been produced there was only a 33.57% turnout percentage.
This discrepancy has been attributed to several factors in the experiment. It is recommended
that to replicate better results better quality reagents must be used and the heat applied in the
reflux must evenly be regulated to prevent formation of by-products. Furthermore,
movements should be more standardized and efficient to prevent experimental errors and
have better turnout results.

References
G., D., & A. (2014). Extraction RCS [PDF]. Department of Chemistry, Ateneo de Manila
University.
"Organic Chemistry Reactions: Speed Study Guides." Google Books. Speedy Publishing
LLC, 3 Sept. 2014. Web. 29 Sept. 2016.
Appendix
1. Determining thelimiting reagent
Acetic Acid :

5.5 mL

1 mol C 7 H 8 O
1.05 g mol C H 3 COOH

=0.09617 mole C 7 H 8 O
mL
60.05 g
1 mol C H 3 COOH

Benzyl Alcohol:

4.5 mL

0.789 g mol C7 H 8 O 1 mol C H 3 COOH

=0.07707 mol C H 3 COOH

mL
46.06844 g
1 mol C 7 H 8 O

Benzyl Alcohol=Limiting Reagent

2.Theoretical Yield :
0.07707 mol C 7 H 8 O

1 mol C 9 H 10 O2
150.18 g
mL

=11.023 mL C 9 H 10 O2
1 mol C 7 H 8 O mol C 9 H 10 O2 1.05 g

3. Percent Yield

Actual Yield
3.7 mL
100=
100=33.57
Theoretical Yield
11.023

4. Experimental Density
Weight of Solution 3.42 g
g
g
=
=1.037
=1.04
Volume of Solution 3.3 mL
mL
ml
5. Percent error

1.051.037 100=1.30
1.05

Theoretical YieldActual Yield

100=
Theoretical Yield