Synthesis of Isopentyl (Amyl) Acetate

Ester (Banana Oil)

Resources
Pavia:
693 697

p. 84 91; 686 688;

Lab Website:
http://classweb.gmu.edu/chemlab
Schornick:

10/20/16

http://classweb.gmu.edu/
jschorni/chem318

Synthesis of Isopentyl (Amyl) Acetate

Ester (Banana Oil)

Overview

Synthesis Acid (H2SO4) catalyzed Fischer Esterification

reaction of a Carboxylic Acid (Acetic Acid) with the
Hydroxyl group of an Alcohol (Isopentyl [Amyl] Alcohol)
This is a Condensation reaction where the molecules
become joined through the intermolecular elimination of
water

10/20/16

Refluxing - Reagents will be Refluxed for about 60

minutes.

Liquid/Liquid Extraction - The product will be washed

several times with Water, Sodium Bicarbonate, Sodium
Chloride

Dry Sample

Refractive Index (with temperature correction)

Infrared Spectrum
2

Synthesis of Isopentyl (Amyl) Acetate

Ester (Banana Oil)

10/20/16

The Laboratory Report:

Synthesis Experiment
Mass, Moles, Molar Ratio, Limiting Reagent,
Theoretical Yield
Procedures
Title Concise: Simple Distillation, Dry Sample,
IR Spectrum, etc.
Materials & Equipment (2 Columns in list
(bullet) form)
Note: include all reagents & principal
equipment used, including details of
distillation setup
Description:
Use list (bullet) form
Concise, but complete description
Use your own words Dont copy book!!
3

Synthesis of Isopentyl (Amyl) Acetate

Ester (Banana Oil)

10/20/16

The Laboratory Report: (Cont)

Results Neat, logically designed template to
present results
Summary experimental results, including
Theoretical Yield results, in paragraph form
Analysis & Conclusions
Limiting reagent
Discuss reaction mechanism in the context of
your experimental results
Verification of product

Synthesis of Isopentyl (Amyl) Acetate

Ester (Banana Oil)

10/20/16

Synthesis of Isopentyl (Amyl) Acetate

Ester (Banana Oil)
Reagents
Acetic Acid
Mol Wgt
130.19 g/mole
Density
0.876
Boiling Point
% Acid
Isopentyl (amyl) Alcohol
Mol Wgt
Density
Boiling Point
Sulfuric Acid
Mol Wgt
Density
% Acid
Molarity
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Product
Isopentyl (amyl) Acetate
- 60.05 g/mole Mol Wgt

- 1.049 g/mL

Density

- 117.9oC Boiling Pnt

- 100% Ref. Index

- 142oC
- 1.4040

- 88.15 g/mole
- 0.809 g/mL
- 130.0oC
-

98.08 g/mole
1.84 g/mL
96.5 %
36 moles/Liter
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Synthesis of Isopentyl (Amyl) Acetate

Ester (Banana Oil)

Heating Under Reflux

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The reaction mixture is heated in a reflux apparatus

consisting of a 25 or 50 mL round bottom flask attached
to a vertical water-cooled condenser set in a heating
mantle.
Liquid/Liquid Extraction

Synthesis of Isopentyl (Amyl) Acetate

Ester
(Banana Oil)

Elements of the Experiment

Equilibrium
Reaction

equilibrium does not favor

formation of the ester

Therefore,

an excess of one of the

reagents (Acetic Acid Cheap!!!) is
used to force the equilibrium to
product side, i.e., to the right

10/20/16

Synthesis of Isopentyl (Amyl) Acetate

Ester
(Banana Oil)

Elements of the Experiment (Cont)

10/20/16

Liquid/Liquid Extraction

The reaction mixture is mixed with Distilled

Water and placed in a separatory funnel
where the phases separate into two layers
Aqueous (higher density) layer on bottom and
the Organic layer on top. Separate the
Aqueous phase into a waste beaker

Extract Organic phase twice with 5% Sodium

Bicarbonate to remove excess acid. Discard
Aqueous phase into waste beaker

Extract Organic phase twice with Saturated

Sodium Chloride to remove excess water.
Discard Aqueous phase into waster beaker
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Synthesis of Isopentyl (Amyl) Acetate

Ester
(Banana Oil)

Elements of the Experiment (Cont)

Dry Product

Dry crude ester (organic

layer) with Anhydrous Sodium Sulfate (less than 1
gram)

Mass of Product

Percent (%) Yield

Refractive Index corrected for temperature

Infrared (IR) Spectrum

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10

Synthesis of Isopentyl (Amyl) Acetate

Ester
(Banana Oil)

10/20/16

Procedure

Measure out ~10 mL of Glacial Acetic Acid to

the nearest 0.1 mL and compute the mass from
the volume and density

Weigh the Isopentyl Alcohol in the vial to the

nearest 0.001 g

Mix the reagents in a Beaker, swirling gently to

ensure complete solution

If necessary, heat gently to help dissolution of

reactants

Carefully add 1.0 mL concentrated Sulfuric Acid

to the mixture mixing (swirling) quickly
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Synthesis of Isopentyl (Amyl) Acetate

Ester
(Banana Oil)

10/20/16

Procedure (Cont)
Set up a Reflux Apparatus using a 50 mL round
bottom flask
Add a Corundum or Teflon (not calcium
carbonate) boiling chip and heat the mixture under
Gentle reflux for 50 60 minutes
Cool the mixture to Room Temperature
Liquid/Liquid Extraction
Pretest the Separatory Funnel to ensure that the
stopper and the stopcock assembly do not leak
Add about 50 mL distilled water to the funnel
Shake vigorously for about 10 seconds
Adjust stopper or stopcock as necessary and
repeat
Drain water from funnel
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Synthesis of Isopentyl (Amyl) Acetate

Ester
(Banana Oil)

Procedure

10/20/16

Liquid/Liquid Extraction (cont)

Transfer the reaction mixture to the

Separatory Funnel using a short neck stem
funnel

Note: Do not transfer boiling chip to funnel

Rinse reaction vessel with 10 mL Distilled

Water and add to mixture in separatory funnel

Mix phases by shaking and venting

Remove the lower aqueous layer and put it

aside for later disposal
13

Synthesis of Isopentyl (Amyl) Acetate

Ester
(Banana Oil)

Procedure (Cont)

Liquid/Liquid Extraction (Cont)

Extract the upper organic layer with 10 mL

aqueous Sodium Bicarbonate (NaHCO3) to
remove excess Acid.

Note:
The reaction between any residual acid
and
Sodium Bicarbonate produces CO2
gas and
could be under considerable
pressure in the
separatory funnel.
Hold the stopper firmly, invert the funnel, and
release the stopcock very slowly so the
venting
of the gas is controlled

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Synthesis of Isopentyl (Amyl) Acetate

Ester
(Banana Oil)

Procedure (Cont)

10/20/16

Liquid/Liquid Extreaction (Cont)

Remove the lower aqueous layer and add to

previous waste aqueous solution

Repeat the NaHCO3 extraction a second time

Perform a third extraction of the upper

organic layer in the Separatory Funnel with
10 mL of saturated Sodium Chloride to
remove excess water

Remove the lower aqueous layer and add to

previous waste aqueous solution

15

Synthesis of Isopentyl (Amyl) Acetate

Ester
(Banana Oil)

Procedure (Cont)

Liquid/Liquid Extraction (Cont)

Repeat the Sodium Chloride extraction a

second time

Transfer the organic layer containing the crude

ester to a small, clean, Erlenmeyer flask

Instructor will add 1.0 g of Anhydrous Sodium

Sulfate
Note: If mixture does not appear to dry
(drying
agent will clump), add
a little more Sodium
Sulfate

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Synthesis of Isopentyl (Amyl) Acetate

Ester
(Banana Oil)

Procedure (Cont)

Allow the mixture to settle

Decant the dried sample into a pre-weighed 100

mL beaker, leaving all solid material in the flask

Reweigh the beaker and determine the mass of

product

Determine percentage yield

Measure the Refractive Index and correct for

temperature

Obtain the IR Spectrum

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