Banana

EXPERIMENT 2
Preparation
of
Banana Flavor
©Mr. A. R. M. Salcedo
Objectives
- prepare a banana flavor via the Fischer reaction
- construct and use a reflux set up
- perform a liquid-liquid extraction
- calculate the percent yield of the preparation of banana flavor
Highlighted Concepts
Esters
O
R C O R
- an organic compound formed in a reaction between an acid and an

alcohol with the elimination of water
- recognized by their very characteristic flavor and odor
- often used as fragrant
Structures of Common Esters
O O O
H3C CH3
C C C
H O H2 C CH CH3 H3C OH CH2 CH2 CH3 H3C O H2C H2C CH CH3
Banana
Raspberry Pear
O O O
H3C
C C C
H3 C O H2C (H2C)6 CH3 H3C O H2C CH3 CH2 O H2C CH CH3
Orange Peach Rum
O O
CH3
C C
H3C H2C H2C O CH2 CH3 H3C H2C H2C O H2C H2C CH CH3
Pineapple Apricot
O
O C
O OCH3
C
C O CH3
H3C H2C H2C O CH3 OH
NH2
Apple Grape Oil of Wintergreen
Preparation of Esters
► Direct esterification of a carboxylic acid with an alcohol (Fischer Esterification)
► Alcoholysis of acid chlorides, anhydrides, or nitriles.
► Reaction of a carboxylic acid salt with an alkyl halide or sulfate.
► Via the trans-esterification reaction.
Fischer Esterification
O O
+ H+
C + R OH C + H3O+
R OH Acid catalyst R OR'
Carboxylic Alcohol Ester Hydronium
acid ion
Reflux
- a method of heating liquid so that
escaping vapor is condensed and
returned to the liquid
- used to heat reaction mixtures

without losing a volatile liquid
- to heat a liquid in a container

with a condenser that catches and
returns escaping vapor
Reflux Set-up
Extraction
- the method of separating a substance from a mixture by dissolving
one or more of the components in a solvent
Liquid-Liquid Extraction
- the method of separating a substance
from a mixture by dissolving one or more
of the components in a solvent
Separatory funnel
Drying Agents
- are anhydrous inorganic salts which react
with water to form insoluble hydrates
Salting Out Effect

- addition of organic salts decreases the solubility
of the organic compounds in water thus assisting
in the extraction by organic solvent
Methodology
Materials and Apparatus
☻ reflux set-up
Reagents
☻ bunsen burner
☻ isoamyl alcohol
☻ boiling chips
☻ acetic anhydride
☻ separatory funnel
☻ conc. sulfuric acid
☻ thermometer
☻ 5% NaHCO3
☻ ice bath
☻ satd. NaCl
☻ vial
☻ anhydrous Na2SO4
Methodology
Preparation
H2SO4
A B
A/B
A/B
REFLUX
A – isoamyl alcohol
B – acetic anhydride
Methodology
Reflux
Water out
15 mL
NaHCO3
Reflux for
Water in
30 mins
Crushed ice
Water bath
at 80°C
Methodology
Washing/Extraction
Upper
Upperlayer
layer
Upper
Upperlayer
layer
+ 15 mL NaHCO3
Lower
Lowerlayer
layer
Lower
Lowerlayer
layer
Methodology
Salting Out & Drying
Upper layer
Anhydrous
+ 15 mL NaCl Na2SO4
Upper layer
cotton
Lower layer
Pre-weighed vial
Data and Results
Volume of Isoamyl alcohol:
» Get the weight of the synthesized
Volume of Acetic Anhydride: banana flavor
Weight of empty vial: » Determine the limiting reagent and

compute the theoretical yield of the
Weight of ester and vial: experiment
Weight of banana flavor: » Compute the percent yield of the

experiment
Theoretical Yield:
Experimental yield
Percent yield:
% yield =
Theoretical yield
Description of banana flavor:
Discussion
Fischer Esterification
O O O O
H2SO4
+ +
HO O O OH
isopentyl alcohol acetic anhydride isopentyl acetate acetic acid
MW = 88.15 g/mol MW = 102.09 g/mol MW = 130.18 g/mol

d = 0.809 g/mL d = 1.080 g/mL d= 0.876 g/mL
V = 2.5 mL V = 2.6 mL V = ? mL
Discussion
Limiting Reagent
Discussion
Theoretical yield
Percent Yield
EXPERIMENT 2
THE END

Banana

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EXPERIMENT 2

- construct and use a reflux set up

- perform a liquid-liquid extraction

- calculate the percent yield of the preparation of banana flavor

- an organic compound formed in a reaction between an acid and an

Orange Peach Rum

► Direct esterification of a carboxylic acid with an alcohol (Fischer Esterification)

► Alcoholysis of acid chlorides, anhydrides, or nitriles.

► Reaction of a carboxylic acid salt with an alkyl halide or sulfate.

► Via the trans-esterification reaction.

- used to heat reaction mixtures

- to heat a liquid in a container

Salting Out Effect

Weight of empty vial: » Determine the limiting reagent and

Weight of banana flavor: » Compute the percent yield of the

isopentyl alcohol acetic anhydride isopentyl acetate acetic acid

MW = 88.15 g/mol MW = 102.09 g/mol MW = 130.18 g/mol

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