CHEMISTRY 125 LABORATORY

Name: Balagao, Sherey Mae U.

Lab Schedule: 1:00-4:00 MW
Group No.: 4

Date Performed: September 24, 2014

Date Submitted: October 1, 2014
Rating:

Exercise No. 11
ESTERIFICATION: PREPARATION OF ISOAMYL ACETATE
I.

OBJECTIVES:
To prepare isopentyl acetate from isopentyl alcohol and acetic acid by the
Fischer esterification reaction.

II.

EXPERIMENTAL RESULTS
O
||
CH3C-OH

+ (CH3)2-CH-CH2-CH2-OH

O
||
CH3C-OCH2-CH2(CH3)2 + H2O

Quantities

3.0 g

17.6 g (22 mL)

------

Mol Wt.

60 g/mol

88g/mol

130g/mol

Mole

0.5mL

0.2mL

------

Theoretical Yield

------

------

26g (0.2mol 130g/mol)

Actual Yield

------

------

10g

Percentage Yield

41.5 %

Mass of pre-weighed bottle

= 31 g
Mass of bottle and isoamyl acetate = 41.7g
Mass of isopentyl acetate = Mass of bottle and isoamyl acetate - Mass of pre-weighed bottle
= 10. 71g
Theoretical yield of isopentyl acetate = 26g
Percent yield = (Actual yield / Theoretical yield) 100%
=
= 41.15%

100

III.

DISCUSSION
Esters are derivatives of carboxylic acids in which the acyl carbon bears an
alkoxy substituent (OR) rather than the hydroxyl substituent (OH) of the acid. Simple
esters tend to have pleasant, fruity odors and are widely used as flavors and fragrances.
They are used in artificial flavorings. Esters are naturally abundant and readily
synthesized, but all have the same following structure shown below;

Esterification, a condensation reaction where two molecules are joined together to

form a larger molecule with the simultaneous loss of water, generally refers to the
formation of esters from alcohol and carboxylic acids, as shown below:

carboxylic
acid

alcohol
(nucleophile)

ester

The reaction proceeds by way of a nucleophilic substitution at the acyl carbon of

the carboxylic acid. When catalyzed by a strong acid, usually sulfuric acid and the
reaction is called as Fischer esterification. The mechanism of fischer esterification can be
summarize into five steps. The acid catalyst is involved in the first step and regenerated
in the last step. The first step is protonation of the carbonyl oxygen, followed by addition
of the alcohol to form a tetrahedral intermediate. The third and fourth steps involve a
proton transfer to form water, a good leaving group. After the water leaves in the fifth
step, there is just the deprotonation of the carbonyl oxygen to form the neutral species.

The mechanism of fisher esterification mentioned is shown below;

Each step of the reaction mechanism is reversible and thus the reaction reaches
equilibrium. The amount of ester produced in an equilibrium reaction might be increased
either by using an excess of one of the reactants or by removing one of the products as
what Le Chateliers principle suggested.
Synthesis of isoamyl acetate, an ester, was done in the experiment. Isoamyl
acetate, also known as isopentyl acetate, is an organic compound that is the ester formed
from isoamyl alcohol and acetic acid. It is a colorless liquid that is only slightly soluble in
water, but very soluble in most organic solvents. Isoamyl acetate is commonly called as
banana oil because of its characteristic odor. The reaction of isoamyl alcohol and acetic
acid is shown below:
O
O
||
H2SO4
||
CH3C-OH + (CH3)2-CH-CH2-CH2-OH
CH3C-OCH2-CH2(CH3)2 + H2O
Acetic acid
Isoamyl alcohol
isoamyl acetate

Isoamyl acetate was prepared by refluxing isoamyl alcohol with excess acetic acid
and sulfuric acid. Sulfuric acid was used to catalyze the reaction and the purpose of reflux
was to heat the reaction mixture at its boiling temperature to form products, without
losing any of the compounds in the flask.Once refluxing was done for about one hour, the
flask was allowed to cool in an ice bath and was then transferred to a separatory funnel.
Then another 100 mL of cold water was added to the funnel. The mixture was then mixed
and the phases were allowed to delayer before the aqueous layer was drained off and
discarded.

After separation was complete, excess acetic acid and sulfuric acid was removed
from the reaction mixture by extraction with sodium bicarbonate (NaHCO3).Sodium
bicarbonate reacts with acetic acid to make sodium acetate and carbonic acid (H2CO3),
but it does not react with isoamyl acetate. Therefore, if proper amount of sodium
bicarbonate solution was used, all of the acetic acid will be converted into water-soluble
sodium acetate and no acetic acid will remain in the solution. With anhydrous
Magnesium sulfate (MgSO4), the solution of isoamyl acetate was allowed to dry for about
30 minutes. Anhydrous MgSO4 can dry an ester solution by trapping small numbers of
water molecules inside its crystal lattice. When MgSO4 adsorbs water, it changes from a
fine powder into larger clumps.

The final product was then obtained by distilling the impure product. The pure
solution of isoamyl acetate was then separated with its boiling point at 137oC-142oC.
Distillation is the process of heating a liquid until it boils, capturing and cooling the
resultant hot vapors, and collecting the condensed vapors. Distillation is used to purify a
compound by separating it from a non-volatile or less-volatile material. When different
compounds in a mixture have different boiling points, they get separated into individual
components when the mixture is carefully distilled.

IV.

CONCLUSION
Isoamyl acetate, an ester was prepared by refluxing isopentyl alcohol with excess
acetic acid and hydrochloric acid. The acetate obtained by distillation yielded 10.71g a
41.15% yield. The boiling point range where isoamyl acetate was collected was at 142oC.
The expected yield to be collected was about 75%, but it was not reached due to some
causes of errors. Some of the product could have been lost during the reflux process. To
decrease this sort of error the heat must be kept at a low level. Another source of error
that may have decreased the yield was when transferring the solution from separatory
funnel to the Erlenmeyer flask or at another part of the procedure during the decanting
process where the product may have been left in the Erlenmeyer flask when transferring
it to distillation flask. To diminish the error for loss of product during the transference
from separatory funnel to Erlenmeyer flask would be wash out the separatory funnel with
diethyl ether, this would get all the product left in the funnel.

V. REFERENCES

Organic Chemistry Laboratory Manual, (2005), CHY 272, Esterification: Preparation of

Isopentyl Acetate, Ryerson University

McMurry, J., (2004), Organic Chemistry, 6th ed., Brooks/Cole Thomson Learning
"preparation of isopentyl acetate." 123HelpMe.com. 29 Sep 2014

<http://www.123HelpMe.com/view.asp?id=82159>.