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Preparation

of
Banana Flavor
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 prepared of banana flavor
Highlighted Concepts
Esters
- 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
R C
O
O R
Highlighted Concepts
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.
Highlighted Concepts
Fischer Esterification
+
C
O
OH R
R OH
+ H
+
C
R
O
OR'
+ H
3
O
+
Carboxylic
acid
Alcohol Ester Hydronium
ion
Acid catalyst
Highlighted Concepts
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
Reflux Set-up
- to heat a liquid in a container
with a condenser that catches and
returns escaping vapor
Highlighted Concepts
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
Highlighted Concepts
Mr. A. R. M. Salcedo
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
Mr. A. R. M. Salcedo
Materials and Apparatus
reflux set-up
bunsen burner
boiling chips
separatory funnel
thermometer
ice bath
vial
Reagents
isoamyl alcohol
acetic anhydride
conc. sulfuric acid
5% NaHCO
3
satd. NaCl
anhydrous Na
2
SO
4
Methodology
A B
A isoamyl alcohol
B acetic anhydride
H
2
SO
4
A/B
A/B
REFLUX
Preparation
Methodology
Water bath
at 80C
Reflux for
30 mins
Crushed ice
Reflux
Water in
Water out
15 mL
NaHCO
3
Methodology
Washing/Extraction
Upper layer
Lower layer
+ 15 mL NaHCO
3
Lower layer
Upper layer
Methodology
Salting Out & Drying
Upper layer
+ 15 mL NaCl
Lower layer
Upper layer
cotton
Anhydrous
Na
2
SO
4
Pre-weighed vial
Data and Results
Get the weight of the synthesized
banana flavor
Determine the limiting reagent and
compute the theoretical yield of the
experiment
Compute the percent yield of the
experiment
% yield =
Experimental yield
Theoretical yield
Volume of Isoamyl alcohol:
Volume of Acetic Anhydride:
Weight of empty vial:
Weight of ester and vial:
Weight of banana flavor:
Theoretical Yield:
Percent yield:
Description of banana flavor:
Discussion
Fischer Esterification
MW = 88.15 g/mol
d = 0.809 g/mL
V = 2.5 mL
MW = 102.09 g/mol
d = 1.080 g/mL
V = 2.6 mL
MW = 130.18 g/mol
d = 0.876 g/mL
V = ? mL
HO
isopentyl alcohol
O O
O
acetic anhydride
+
+
O
O
isopentyl acetate
H
2
SO
4
OH
O
acetic acid
Discussion
Limiting Reagent
Discussion
Theoretical yield
Percent Yield