Banana Oil Lab Report

Synthesis of Isopentyl Acetate using a Fischer Esterification Reaction

Morgan Burkhart

TA: Derek Saxon

Section 05

October 6, 2016

PURPOSE

Isopentyl acetate, commonly known as banana oil, was synthesized using an acid

catalyzed Fischer esterification reaction. The desired product was purified by distillation,

and characterized by boiling point, IR and 1H NMR spectroscopy to confirm identity and

purity of product.

REACTION SCHEME

O

+

OH

Acetic Acid

O

HO S OH

O

HO

O

+

O

Isopentyl Alcohol

Isopentyl Acetate

MECHANISM

Equilibrium occurs between water and the acid catalyst, sulfuric acid.

O

HO S OH

O

H

O

H

H

H

O

H

O

HO S O

O

O

H

H

Water

Fischer esterification synthesized isopentyl acetate from carboxylic acid and alcohol.

H

O

+

H

OH

H

O

HO OH

+

O

OH

H

O

H

HO

H

H

H

O

H

H

HO

OH

HO

H

O

H

O

O

H

H

HO OH

O

H

H

H

O

O

H

O

O

O

O

O

PROCEDURE

The procedure was completed following the procedure on page 33 of Wissinger

manual.1

REAGENTS TABLE

Acetic

 Acid

Moleular

 Weight

 (g/mol)

60.05

Grams

9.03

Moles

0.15

Density

 (g/mL)

1.05

mL

8.6

Boiling

 Point

117°C-­‐118°C

Isopentyl

Alcohol

88.15

5.02

0.057

0.809

6.2

130°C

Isopentyl

Acetate

Sulfuric

 Acid

130.18

98.08

4.702

2.2

0.036

0.02

0.876

1.84

5.38

1.2

142°C

290°C

*Acetic acid was used in excess

*Sources (2) and (3)

RESULTS AND OBSERVATIONS

Observations:

During reflux, liquid solution turned very dark, nearly black. A wash with water in

the separatory funnel resulted in a dark brown organic layer and a dark brown/reddish

colored aqueous layer. When the organic layer was...