Title: Preparation of Ester present in banana oil.

Objective: To synthesize isopentyl acetate an ester, by an esterification reaction between acetic

acid and isopentyl alcohol and using concentrated sulfuric acid.

Materials needed: Hot plate, magnetic stirring bar, clamps, condenser, rubber hose (2), round bottom
conical flask, evaporating dish with sand, separatory funnel, ring stand, boiling chips, rubber tubings,
pipette, aspirator and graduated cylinder.

Chemicals needed: 15 mL 3-methyl-1-butanol,15 mL Acetic acid, 5 mL concentrated HSO or

HPO, 50 mL deionized water, 25 mL sodium bicarbonate solution, and phenolphthalein.

Procedure:

1. Take 15 mL 3- methyl- 1-butanol (isoamyl alcohol or ispentyl alcohol) and add 15 mL acetic
acid along with, 5 mL concentrated sulfuric acid or phosphoric acid.

2. Boil for 1 hour.

3. Stop heating and cool to room temperature.

4. Transfer the mixture to a separatory funnel and add 50 mL deionized water and mix the
solution.

5. Drain off lower layer, and add 25 mL sodium bicarbonate solution into the separatory funnel.

6. Drain off lower layer again.

7. Transfer upper layer into distillation flask and set up distillation apparatus using condenser and
sand bath.

8. Boil at 132-143 C.

9. Dispose distillate that was collected below 132 C, and collect distillate above temperature of
132C.

10. To test the purity of this distillate, take distillate in test tube, add deionized water and 1-2
drops of phenolphthalein. If the solution turns pink, then the solution is pure.

Results and Data:

Compound Result

Addition of 3- methyl-1-butanol+ 15 mL acetic Clear solution

acid + 5 mL concentrated phosphoric acid.

After boiling for 1 hour and cooling to room Clear light yellow solution and smelled like
temperature banana

Addition of 50 mL deionized water Bottom layer clear and top layer frothy yellow

Addition of 25 mL sodium bicarbonate Bottom layer clear, top layer frothy yellow
with formation of bubbles

Distillate collected above 32C Clear solution

Addition of phenolphthalein and deionized Solution turned pink

water

Discussion:

Esters are found widely in nature, and low molecular weight esters have pleasant taste and odor.
The functional group of an ester can be linear or branch chain aliphatic. Esters can be
synthesized by many methods and a example of a method is fisher esterification. In this method
esters are produced by refluxing a carboxylic acid and an alcohol in the presence of a
concentrated acid catalyst. In fishers method only primary and secondary alcohols, since tertiary
alcohols are prone to elimination. This method is also an equilibrium reaction, where other
esterification reactions dont involve equilibrium. To shift equilibrium to favor production of
esters, an excess of one of the reactants have to be use, and an excess of acetic acid is commonly
used because it is cheaper and easier to remove than alcohol. In this lab we synthesized
isopentyl acetate from isopentyl alcohol and acetic acid.

Conclusion:

In conlusion in this experiment, we created isopentyl acetate by fischer esterification. The

mechanism for this reaction is the nucleophilic addition of alcohol to the carbonyl group of
protonated acid, followed by elimination of proton. The tetrahedral intermedicate formed is
unstable under acidic conditions and undergoes dehydration to form an ester. Our distillate
obtained was pure as it turned pink when phenolphthalein and deionized water were added.