Banana Synthesis of Ester

SYNTHESIS OF ESTER- ISOAMYL
ACETATE (BANANA FLAVOR)BY

FISCHER REACTION
Mendoza, Edsel Daniel
Peafiel, Mark Rean
Raada, Mary Pauline
Sy, Patryk Renzo
Tubig, Nicholas
2P4
INTRODUCTION
Esters- any class of mostly fragrant

compounds that are formed by the reaction
between an acid and alcohol with
elimination of water, it can be synthetically
produced by the use of Fischer Reaction.
INTRODUCTION
Fischer esterification- first described by

Emil Fischer (1895) is the treatment of
carboxylic acid with an alcohol with an
acid catalyst to form esters (Franklin
and Hippelinen, 2012).
OTHER ESTERS OF DIFFERENT

FLAVORS
Alcohol
Carboxylic acid
Ester(product)
Fragrance
Isoamyl alcohol
Acetic
anhydride
Isoamyl acetate
Banana
Octanol
Acetic acid
Octyl Acetate
Orange
Methanol
Salicylic acid
Methyl
Salicytate
Wintergreen
Propanol
Acetic acid
Propyl acetate
Pear
Benzyl alcohol
Acetic acid
Benzyl acetate
Peach
Butanol
Butyric acid
Butyl butyrate
Pineapple
Ethanol
Butyric acid
Ethyl butyrate
strawberry
OBJECTIVES
At the end of the experiment, we should be
able to:
Synthesize the Isoamyl acetate
Calculate for the percent yield
BACKGROUND INFORMATION
Chemicals used:
Isoamyl Alcohol (CH3)2CHCH2CH2OH
Acetic Anhydride C4H6O3
Sulfuric Acid H2SO4
Sodium bicarbonate NaHCO3
Sodium Sulfate Na2SO4
Isoamyl Acetate C7H14O2
Chemical
Description
Application
Isoamyl Alcohol
clear, colorlessalcohol
Used as
anantifoaming
agentin the
Chloroform: Isoamyl
Alcohol reagent
main ingredient in the
production ofbanana
oil
Acetic Anhydride
flexible molecule with

a nonplanar structure
versatile reagent
foracetylation
Commonly used as an
acetylating agent
Chemical
Description
Application
Sulfuric Acid
Highlycorrosivestrong
mineral acid;
Pungent-ethereal,
colorless to slightly
yellow viscous liquid
Soluble inwateratall
concentrations
Used in large
quantities by
ironandsteelmaking
industry to remove
rust
White solid that is

crystallinebut often
appears as a fine
powder
Prepared by the
reaction ofsodium
chloride,ammonia,
andcarbon dioxidein
water
Can be used to
extinguish small
grease or electrical
Wash to remove any
acidic impurities
Removing paint and
corrosion
Sodium bicarbonate
As an acid catalyst
Chemical
Description
Application
Anhydrous Sodium
Sulfate
Sodiumsalt ofsulfuric
acid. Whenanhydrous,
it is a white crystalline
solid
Contains no water
Manufacture
ofdetergentsand in
theKraft processof
paperpulping
Drying agent to
remove water from a
solution
Isoamyl Acetate
Organic compound
Esterformed
fromisoamyl
alcoholandacetic acid
Colorless liquid;
Slightly soluble in
water; Very soluble in
most organic solvents;
Strong odorand low
toxicity.
Used to confer banana

flavor in foods
Used to attract large
groups of honeybees
to a small area (Boch,
1962)
Used to test the
effectiveness
ofrespiratorsorgas
masks
PROCEDURES USED
Reflux Set Up
Liquid-Liquid Extraction(through
Separatory Funnel)
REFLUX SET UP
Distillation technique involving

thecondensationof vapors and the return of
this condensate to the system from which it
originated (Henry, 1992).
Reflux Setup
LIQUID-LIQUID
EXTRACTION(THROUGH
SEPARATORY
FUNNEL)
extraction of a substance from one liquid into
another liquid phase

method to separate compounds based on their
relativesolubilitiesin two different immiscible
liquids, usually water and an organic solvent.
Aseparatory funnel, is used inliquid-liquid
extractionsto separate the components of a
mixture into twoimmisciblesolventphases of
different densities
Separatory Funnel
METHODOLOGY
Isoamyl Alcohol (A)

(5.0ml)
Acetic Anhydride (B)

(5.2ml)
-Added 5
drops of
H2SO4
-Placed in
ice bath
-Placed
in ice
bath
Reflux Set-up
Separatory funnel
-Added 2 pcs.
Of boiling
chips
-Boiled in H20
bath at 7580c for 30
mins.
-Poured in a
50 ml beaker
which
contained
crush ice
-removed
boiling chips
Separatory funnel
-Added 15 ml saturated
(NaHCO3)
-Swirled
-Drained
Lower layer
Upper layer
-Added 15 ml
saturated
(NaHCO3)
-Swirled
-Drained
Lower layer
Upper layer
Upper layer
-Added 15 ml
saturated
NaCl
-Swirled
-Drained
Lower layer
Upper layer
Discarde
d
Residue
Isoamyl Acetate
-Drained in
50 ml
beaker
-Added
spatula of
anhydrous
Na2SO4
-Swirled
-Decanted
-in a pre
weighed
vial
-weighed
again
Calculated
%yield
RESULTS
*Theoretical yield:
0.0459 x 1 x 130.2 = 5.9762
*Number of moles C4H6O3 (Acetic Anhydride):
5.2mL x 1.0820g/1mL x 1mol/102.09g = 0.05511 mol
*Number of moles of
C5H12O (Isoamyl Alcohol):
5mL x 0.8092g/1mL x
1mol/88.146g = 0.459 mol
2C5H12O + C4H6O3
+ H2O
2C7H14O2
Group 1
Table of Data and Results
Volume of Isoamyl Alcohol
5.0 ml
Density of Isoamyl Alcohol
0.8092 g/ml
Molecular weight of Isoamyl Alcohol
88.146 g/mol
Number of moles of Isoamyl Alcohol
0.04590 mol
Volume of Acetic Anhydride
5.2 mL
Density of Acetic Anhydride
1.0820 g/mL
Molecular weight of Acetic Anhydride
102.09 g/mL
Number of moles of Acetic Anhydride
0.0551 moles
Molecular weight of Isoamyl Acetate
130.2 g/mol
Theoretical Yield
5.9762 g
Weight of empty vial
19.2539 g
Weight of product
4.7524 g
Percent Yield
79.52%
Description of product
Colorless liquid-like, strong vanillalike scent
Group 1
Percent Yield = actual

yield/theoretical yield x
100
% yield = 4.75/5.98 x 100
=79.52%
Group 2
5.0 ml
0.8092 g/ml
88.146 g/mol
0.04590 mol
5.2 mL
1.0820 g/mL
102.09 g/mL
0.0551 moles
130.2 g/mol
Theoretical Yield
5.9762 g
10.62 g
Weight of product
5.65 g
Percent Yield
94.48%
Colorless product, banana scent,

smells good
Group 2

100
% yield = 5.65/5.98 x 100
= 94.48%
Group 3
5.0 ml
0.8092 g/ml
88.146 g/mol
0.04590 mol
5.2 mL
1.0820 g/mL
102.09 g/mL
0.0551 moles
130.2 g/mol
Theoretical Yield
5.9762 g
11.4153 g
Weight of product
4.1187 g
Percent Yield
68.93%
colorless
Group 3

100
% yield = 4.1187/5.9762 x
100 = 68.93%
Group 4
5.0 ml
0.8092 g/ml
88.146 g/mol
0.04590 mol
5.2 mL
1.0820 g/mL
102.09 g/mL
0.0551 moles
130.2 g/mol
Theoretical Yield
5.9762 g
15.1304 g
Weight of product
4.0292 g
Percent Yield
67.42%
Colorless thick oily liquid, smells

concentrated
Group 4

100
% yield = 4.0292/5.9762 x
100 =67.42%
Group 5
5.0 ml
0.8092 g/ml
88.146 g/mol
0.04590 mol
5.2 mL
1.0820 g/mL
102.09 g/mL
0.0551 moles
130.2 g/mol
Theoretical Yield
5.9762 g
14.3097 g
Weight of product
4.0397 g
Percent Yield
67.55%
Colorless, banana-like smell
Group 5

100
% yield = 4.04/5.98x 100
=67.55%
Group 6
5.0 ml
0.8092 g/ml
88.146 g/mol
0.04590 mol
5.2 mL
1.0820 g/mL
102.09 g/mL
0.0551 moles
130.2 g/mol
Theoretical Yield
5.9762 g
11.2334 g
Weight of product
4.0460 g
Percent Yield
67.70%
Colorless liquid, banana-like smell
Group 6

100
% yield = 4.0460/5.9762 x
100 = 67.70%
Group 7
5.0 ml
0.8092 g/ml
88.146 g/mol
0.04590 mol
5.2 mL
1.0820 g/mL
102.09 g/mL
0.0551 moles
130.2 g/mol
Theoretical Yield
5.9762 g
21.38 g
Weight of product
4.33 g
Percent Yield
72.46%
Colorless liquid like water, strong

smell of banana
Group 7

100
% yield = 4.33/5.9762 x
100 =72.46%
Group 8
5.0 ml
0.8092 g/ml
88.146 g/mol
0.04590 mol
5.2 mL
1.0820 g/mL
102.09 g/mL
0.0551 moles
130.2 g/mol
Theoretical Yield
5.9762 g
12.3712 g
Weight of product
3.28 g
Percent Yield
54.88%
Colorless liquid, banana-like strong

smell
Group 8

100
% yield = 3.28/5.9762 x
100 = 54.88%
Group 9
5.0 ml
0.8092 g/ml
88.146 g/mol
0.04590 mol
5.2 mL
1.0820 g/mL
102.09 g/mL
0.0551 moles
130.2 g/mol
Theoretical Yield
5.9762 g
16.1025 g
Weight of product
3.1407 g
Percent Yield
52.55%
Colorless candy-like scent, banana

candy scent
Group 9

100
% yield = 3.1407/5.9762 x
100 = 52.55%
Group 10
5.0 ml
0.8092 g/mL
88.146 g/mol
0.04590 moles
5.2 mL
1.0820 g/mL
102.09 g/mL
0.0551 moles
130.2 g/mol
Theoretical Yield
5.9762 g
12. 17 g
Weight of product
4.3464 g
Percent Yield
72.7285%
Colorless liquid, concentrated banana

flavor
Group 10

100
% yield = 4.3464/5.9762 x
100 = 72.7385%
COMPARISONS OF % YIELD
OF GROUPS 1-10
100
Group
Percent yield
79.52%
94.98%
68.93%
50
67.42%
40
67.55%
30
67.70%
20
72.46%
10
54.88%
52.55%
10
72.74%
90
80
70
y
i
e
l
d
60
5
Groups
10
Group 10

100
% yield = 4.3464/5.9762 x
100 = 72.7385%
WEIGHT OF PRODUCT
Group
Weight of
product
4.75 g
5.75 g
4.12 g
4.03 g
4.04 g
4.05 g
4.33 g
3.28 g
3.14 g
10
4.35 g
Isoamyl Alcohol (A)

(5.0ml)
Acetic Anhydride (B)

(5.2ml)
ESTERIFICATIO
N
Reflux Set-up
SOLUBILITY
Separatory funnel
EXTRACTION
Separatory funnel
Saturated
NaHCO3
EXTRACTION
Lower layer
Upper layer
Saturated
NaHCO3
EXTRACTION
Lower layer
Upper layer
Upper layer
DRYING
Saturated NaCl
Extraction
Lower layer
Upper layer
Anhydrous
Na2SO4
Extraction
Residue
Isoamyl Acetate
PRINCIPLES BEHIND THE

EXPERIMENT
SOLUBILITY
Neutralization
Drying
SOLUBILITY
Acetic acid and Sulfuric acid are washed away by

H2O because the two are water soluble
Water cools down the reaction
NEUTRALIZATION
Saturated NaHCO3 (amphoteric) removes

excess acetic acid and acid catalyst
(H2SO4)
DRYING
DRYING AGENTS:
1. Saturated NaCl
Salts have stronger attraction to water
organic solvents
2. Anhydrous Na2SO4
than
inorganic salt which takes up water to become

hydrated
POSSIBLE SOURCES OF ERROR

Results and data may have been affected by
the following deviations:
Improper use or using different materials for
the experiment
Incorrect following of procedures
Improper extraction and draining
Timing
Inexact amount of added compound

Contaminated materials and containers
CONCLUSION
Every group was able to prepare and

execute Fischer esterification and liquidliquid extraction .
Every group was able to calculate the
percent yield of their product
Average percent yield : 76.67%
REFERENCES
Ester.2015. Encyclopdia Britannica retrieved from

http://www.britannica.com/EBchecked/topic/193393/ester
Franklin and Hippelinen. (2012). FISCHERSPEIER

ESTERIFICATION ORGANIC SYNTHESIS & THE HISTORICAL
METHOD. Retrieved from
http://ouluma.fi/wp-content/uploads/2012/04/ficherspeier_esterification.pdf
REFERENCES
Zumbo, P."Phenol-chloroform Extraction". WEILL CORNELL

MEDICAL COLLEGE P. ZUMBO LABORATORY OF CHRISTOPHER E.
MASON, PH.D. Retrieved19 June2014.
Boch R; Shearer DA; Stone BC (September 8, 1962).

"Identification of isoamyl acetate as an active component in the
sting pheromone of the honey bee.".Nature(England: Nature
Publishing Group)195(4845): 101820
"Arm & Hammer Baking Soda Basics The Magic Of Arm &
Hammer Baking Soda Retrieved from ArmHammer.com
Kister, Henry Z. (1992).Distillation Design(1st Edition ed.).

McGraw-Hill.

Banana Synthesis of Ester

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Banana Synthesis of Ester

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SYNTHESIS OF ESTER- ISOAMYL

ACETATE (BANANA FLAVOR)BY

Esters- any class of mostly fragrant

Fischer esterification- first described by

OTHER ESTERS OF DIFFERENT

Calculate for the percent yield

flexible molecule with

White solid that is

Used to confer banana

Distillation technique involving

another liquid phase

Isoamyl Alcohol (A)

Acetic Anhydride (B)

0.0459 x 1 x 130.2 = 5.9762

*Number of moles C4H6O3 (Acetic Anhydride):

5.2mL x 1.0820g/1mL x 1mol/102.09g = 0.05511 mol

C5H12O (Isoamyl Alcohol):

Density of Isoamyl Alcohol

Molecular weight of Isoamyl Alcohol

Number of moles of Isoamyl Alcohol

Volume of Acetic Anhydride

Density of Acetic Anhydride

Molecular weight of Acetic Anhydride

Number of moles of Acetic Anhydride

Molecular weight of Isoamyl Acetate

Weight of empty vial

Colorless liquid-like, strong vanillalike scent

Percent Yield = actual

Density of Isoamyl Alcohol

Molecular weight of Isoamyl Alcohol

Number of moles of Isoamyl Alcohol

Volume of Acetic Anhydride

Density of Acetic Anhydride

Molecular weight of Acetic Anhydride

Number of moles of Acetic Anhydride

Molecular weight of Isoamyl Acetate

Weight of empty vial

Colorless product, banana scent,

Percent Yield = actual

Density of Isoamyl Alcohol

Molecular weight of Isoamyl Alcohol

Number of moles of Isoamyl Alcohol

Volume of Acetic Anhydride

Density of Acetic Anhydride

Molecular weight of Acetic Anhydride

Number of moles of Acetic Anhydride

Molecular weight of Isoamyl Acetate

Weight of empty vial

Percent Yield = actual

Density of Isoamyl Alcohol

Molecular weight of Isoamyl Alcohol

Number of moles of Isoamyl Alcohol

Volume of Acetic Anhydride

Density of Acetic Anhydride

Molecular weight of Acetic Anhydride

Number of moles of Acetic Anhydride

Molecular weight of Isoamyl Acetate

Weight of empty vial

Colorless thick oily liquid, smells

Percent Yield = actual

Density of Isoamyl Alcohol

Molecular weight of Isoamyl Alcohol

Number of moles of Isoamyl Alcohol

Volume of Acetic Anhydride