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Synthesis & Distillation of Isopentyl Acetate using Acetic Acid and

Isopentyl alcohol

TA: Pallav Kumar


TH 2:00-3:00

Abstract:
Isopentyl Acetate (Banana oil) was synthesized by combining a carboxylic acid
with an alcohol forming an ester (isopentyl alcohol). In FIG. 1 the reaction showed acetic
acid and isopentyl alcohol being combined to form isopentyl acetate. For the reaction to
proceed a reflux technique was used. After the synthesis was performed a distillation
procedure was performed to purify the isopentyl acetate. The boiling point for the
purified isopentyl acetate was approximately 139.5C. There were still a few impurities
for the purified sample as the boiling point showed, and the calculated percentage yield
was 54%.

FIG.1. Reaction of acetic acid and isopentyl alcohol reacting to form isopentyl acetate.

Introduction:
Isopentyl acetate is a colorless liquid that is only slightly soluble in water, but
very soluble in most organic solvents. Isopentyl acetate has a strong odor; it smells very
much like a banana. It is used as a solvent for some varnishes and nitrocellulose lacquers,
as well as being a honeybee pheromone and can be used to attract large groups of
honeybees to a small area. The intense smell, pleasant odor and low toxicity of isopentyl
acetate help to test the effectiveness of respirators or gas masks. In the experiment
isopentyl alcohol was treated with acetic acid to synthesize acetaminophen, and was
induced by using a reflux. A distillation method was then applied to purify the isopentyl
acetate.

FIG.2. The overall reaction shows an addition reaction, where the acetic acid
becomes deprotonated and a ester group exchanges places with it.

Fig.3. The image above shows the mechanism

Figure 3. shows in detail how the mechanism was performed, what happened in
the first step was the carboxylic acid accepted a proton from the strong acid catalyst, then
the non-bonded electrons of the alcohol attacked the positively charged carbonyl carbon
to give a intermediate. A proton was lost at the oxygen and gained at another. The
mechanism then lost a water molecule giving a protonated ester. The last step in the
mechanism was the transfer of a proton from the second hydroxyl group, which forms the
ester (the product). Determining the boiling point and percent recovery would determine
the success of the experiment. The boiling point of the final compound was determined
and compared to the literature boiling point, which was 140C. If the boiling point of
the purified isopentyl acetate were more/less than 5 degrees from the literature boiling
point then it would have not been accurate and could not support the identity of isopentyl
alcohol. Percent recovery was measured by the taking actual amount of grams of
isopentyl acetate obtained divided by the theoretical number of grams that should have
been produced.
The goal of the lab was to synthesize isopentyl acetate correctly and perform the
procedures in order to get a pure sample of the ester and a great percent recovery. A
possible problem that could have occurred would have been that there could have been
impurities still left in the final product, or the temperature not being constant could have
played a factor when doing the reflux and distillation.

Procedure:
To begin the experiment, an empty 5-ml conical vial was weighed and 1.0 ml of
isopentyl alcohol was added, a reflux was assembled (a drying tube contained calcium
chloride was attached to reflux). The conical vial containing the alcohol was then
reweighed to obtain an accurate weight. Then 1.5 mL of glacial acetic acid was added,;
three drops of concentrated sulfuric acid were added carefully to the vial. A small
magnetic spin vane was added to the vial and heated. The vial containing the compounds
where then refluxed for 70 minutes at 160. After the 70 minutes the vial was removed
from the heat and cooled to room temperature. Using a pipet 1.0 mL of sodium
bicarbonate was used to separate organic and aqueous layers (done 3 times total). The
bottom aqueous layer was then removed and disposed. The organic layer (isopentyl
acetate) was then dried with sodium sulfate. The next method used was distillation, using
a still head and a water-cooled condenser, which was used to purify the isopentyl acetate.
The final product was then weighed and percent yield and boiling point taken, and two
infrared spectrum graphs were obtained.

Results and Calculations:


Table 1. Comparison of literature b.p. and weight of initial and final product
Boiling Point (C)
140

Literature
Initial
Final

Weight (g)
1.0
0.628

139.5

Limiting Reagent, Theoretical Yield, and Percent Yield:


1.5mL glacial acetate x 1.06g/mL= 1.59g
1.59g x 1mol =0.0264mol glacial acetate
60.1g
1.0mL isopentyl alcohol x 0.813g/ml= 0.813
0.813g x 1mol = 0.0092mol isopentyl alcohol
88.2g

limiting reagent

Theoretical Yield:
0.0092mol isopentyl alcohol x 130mol isopentyl acetate = 1.196 g
Percent Yield:
0.628g actual
1.192g theoretical

x 100 = 52.37% percent yield purified isopentyl acetate

Discussion and Conclusions:

Based on our results of synthesizing and distilling isopentyl acetate, it was found
that the boiling point of the purified isopentyl acetate was very similar to the literature
boiling point Therefore, the purified sample of isopentyl acetate produced was reasonably
pure, so this demonstrates that the reflux, workup, and distillation procedures were done
successfully. However, on the other hand the percent yield was only 54% for the final
product. Although the percent yield seems to be low, the aqueous component and the
impurities were removed during distillation and the workup; therefore the compound lost
mass throughout the experiment, which is what was expected. But over the other parts of
the experiment the isopentyl acetate could have been lost due to not heating at the right
temperature, the distillation process could have been set for a longer time to make sure
there were no impurities. Overall, the boiling point of our final compound product
matched that of the literature boiling point of the ester, which suggests that the product
was free of a lot of impurities. However, our percent yield was a little more than half of
what was expected. To successfully synthesize isopentyl acetate, it is important for the
product to be pure, thus necessary to remove aqueous compounds and impurities. The
infrared spectroscopy graph also confirmed that the product was pure enough. The peaks
shown on the graphs show an ester and an sp3 C-H bond.

Work Cited

"Molecule of the Week." American Chemical Society - The World's Largest Scientific
Society. American Chemical Society, 15 Oct. 2007. Web. 15 Nov. 2011.
<http://portal.acs.org/portal/acs/corg/content?_nfpb=true>.