F.

Lorenzo Martin Abella Puno

Radito Banzon

Locker: 1B
November 2nd, 2015

Preparation of Benzyl Acetate Postlab

Data and Results:
Table 1.1 Quantitative Data
Volume Benzyl Alcohol (ml)

4.5

Volume of Acetic Acid added (ml)

5.5

Mass of Organic Layer (g)

4.17

Percent Yield (%)

64.16%
Table 1.2 Qualitative Analysis Data

Test

Result

Indicator

Chromic Acid

-, brown solution, no
formation blue-green
precipitate

absence of primary and

secondary alcohols

Hydroxamic Acid

+, formation of a red-violent
solution

presence of ester

Discussion:
A 100% yield would not be expected in this experiment because there are a lot of factors
that can affect the yield. According to table 1.1, there was a 64.16% yield. This is quite a high
yield as it is above 50% but it is not close to a 100% yield, which should not be expected. This
amount of yield could be due to experimental errors and unavoidable errors during the lab. A
reflux setup was used in this experiment. There is a very high possibility that there could have
been leaks in the setup, affecting the percent yield. Another possible experimental error could be
during the draining process. Maybe when the first layers were drained some of the organic layer
could have accidentally be drained as well. This could very much reduce the percent yield.
Lastly, whenever the solution was transferred to different apparatus some solution could have
been left in the previous beaker or flask. <Question 1>

Not only was the percent yield quite high, but the solution was also pure as it test
correctly for all the qualitative tests done. Three qualitative tests were done: Chromic Acid test
and Hydroxamic Acid test. Chromic Acid test is used to determine the presence of benzyl
alcohol, the reactant. Hydroxamic Acid test is used to determine the presence of the product,
benzyl acetate. This test is used because it tests for the presence of an ester functional group, a
functional group that benzyl acetate contains. However, based on the results the product can be
considered pure because using the qualitative tests it was negative to Chromic Acid but positive
to Hydroxamic Acid Test(table 1.2). The presence of water can affect the purity of the product as
the presence of water is the cause of the possible formation of the reactant. Any impurities or
contaminations would also affect the results of the qualitative test. <Question 2>.
The benzyl acetate is extracted first using liquid-liquid extraction prior to distillation to
minimize any contaminations and impurities to be present in the product. If the solution was
distilled first before using liquid-liquid extraction it is possible that traces of water, acetic acid,
and unreacted benzyl alcohol could enter the receiving flask. <Question 3>.
Other derivatives of acetic acid tare acemetacin, indometacin and bumadizone. Although
these derivatives will readily react with benzyl alcohol to form benzyl acetate, the synthesis of
benzyl acetate through esterification is used because there is less formation of side products.
When benzyl acetate is prepared with acetic acid and benzyl alcohol, the only side product that
will form is H20. <Question 4>
Sample Calculations:
Mass of Benzyl Alcohol CalculationsDensity of Benzyl Alcohol: 1.04g/cm3
Density=Mass/Volume
M
1.04 = 4.5ml
M = 4.5 x 1.04
M = 4.68g

Percent Yield Calculation1 mol of Benzyl Alcohol

4.68g of Benzyl Alcohol 108.14
g Benzyl Alcohol = 0.0433 mol Benzyl Alcohol
of Benzyl Acetate
0.0433 mol of Benzyl Alcohol 11mol
mol of Benzyl Alcohol = 0.0433 mol of Benzyl Acetate

of Benzyl Acetate
0.0433 mol of Benzyl Acetate 150.18g
1 mol of Benzyl Acetate = 6.499g of Benzyl Acetate
4.17 g of Benzyl Acetate
6.499 g of Benzyl Acetate

= 0.6416 100 = 64.16%

References:
Guidote Am, del Rosario DR, Abuzo AL. Experiencing Organic Chemistry. Quezon City
Office of Research and Publications, Ateneo de Manila University; 2005.