Lab #12 Isopentyl Acetate

Abstract
A 36.4% yield of isopentyl acetate was obtained via an acid catalyzed
nucleophilic acyl substitution with 5 milliliters of isopentyl alcohol and 7
milliliters of acetic acid in the presence of an acid catalyst. The solution was
heated under reflux conditions and then transferred to a separatory funnel
where three extractions were performed. The purified product was collected

by simple distillation and a boiling point of 137C was observed; an infrared

spectrum analysis was also performed showing the expected absorptions but
also indicated a slightly hydrated product.
Purpose
The purpose of this lab was to introduce students to heating under
reflux and the reaction of acid catalyzed nucleophilic acyl substitution by
synthesizing a sample of isopentyl acetate. Techniques such as extraction,
use of a drying agent, separatory funnel use, simple distillation, and infrared
analysis were revisited.
Isopentyl Acetate is more commonly known by the fragrance of banana
oil. Many simple esters are pleasant smelling and are often used in food and
beverage flavorings. More commonly referred to as essential oils these
compounds are volatile and give off a strong scent. Unfortunately simple
ester fragrances are easily hydrolyzed and thus unstable in the presence of
aqueous or acidic solutions. 1

Reaction
H3C

O
H3C

OH
H

OH

CH3

CH3

H3C

CH3

H2O

Mechanism

O
HO S

OH

O
H3C

OH

H3C

CH3

H3C

OH

H2O

CH3

CH3

H2O

OH

OH

OH

H3C

OH

H3C

OH
OH

CH3
HO

CH3

CH3

H3C

O
CH3

CH3

H2O

CH3

Competing Side Reaction

The competing side reaction for this experiment is the reverse reaction or
hydrolysis of isopentyl acetate by the addition of water.
O
H3C

CH3
O

CH3

H3C

H2O
H3C

OH

OH

CH3

Separation Scheme

5mL Isopentyl Alcohol

7mL Acetic Acid
Purified product
Heat (reflux 1 hour)
distill

Distillate (discard)

Reaction mixture
10mL H2O

Crude Product

Aqueous Layer(discard)

H2O (discard)
Saturated MgSO4

Organic Layer
5mL 5% aq sodium bicarbonate

Organic Layer
Anhydrous MgSO4

Aqueous Layer(discard)
Aqueous Layer (discard)

Layer +

Organic

5mL saturated NaCl

Procedure
The procedure was conducted in accordance with experimental
procedure 12 in the textbook, except that the drying tube packed with
calcium chloride to be placed on top of the condenser was omitted.
Anhydrous magnesium sulfate was used as a drying agent instead of
anhydrous sodium sulfate .1

Physical Constants1,2
Compou
nd
Isopentyl
Alcohol
Isopentyl
Acetate
Glacial
Acetic
acid

Molecular
Formula

Molecular
Weight (g)
88.1

Density(g/ml
)
.81

Boiling
Point (C)
131-132

C5H12O
C7H14O2

130.2

.88

142

C2H4O2

60.1

1.06

118

Calculations
A. Limiting Reagent
5 mL Isopentyl alcohol C5H12O .81 g C5H12O 1 mole C5H12O 1 mole
C7H14O2

1mL C5H12O 88.1 g C5H12O

mole C5H12O
= .046 moles C5H12O
Isopentyl alcohol is the Limiting Reagent
B. Excess Reagent
7 mL Glacial Acetic Acid
C7H14O2

1.06 g C2H4O2 1 mole C2H4O2

1mL C2H4O2

60.1 g C2H4O2

1 mole
1

mole C2H4O2
= .123 moles C2H4O2 (Excess Reagent)
C. Theoretical Yield
(Limiting moles)(Ratio)(Molecular Weight of Product)
(.046 moles C5H12O)(1:1)(130.2 g/mol C7H14O2)
= 5.99 grams C7H14O2
Actual Yield and Percent Yield
Crude Product Mass = 2.18 grams
Percent Yield = (Actual/Theoretical) 100%
(2.18/5.99)100 = 36.4 % yield
D. Analytical Data
The lower percent yield of 36.4% was most likely due to the loss of
product from the system during extractions, container transfers, and
evaporation. The boiling point observed (137C) is approaching that of
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pure isopentyl acetate literature value of 142C which indicates with a few
impurities present. The IR spectra analysis had the corresponding peaks
(see printout for analysis), but also indicated a small amount of alcohol
apparent due to the broad absorption at 3600-3400 cm-1. (Note* The
Hydrogen NMR and Carbon NMR attached were given as a handout and
not performed in the lab). 2
Spectra3

O-H

C-H
Aliphatic

C=

C-O

C-O

The above IR spectra indicates a small amount of alcohol present due

to the medium broad absorption at 3600-3400 cm-1 but could also be the
C=O overtones as well. The carboxyl group shows a strong absorption at
1740 cm-1 while the C-O shows as two bands from 1300-1000 cm-1. The
aliphatic C-H bonding is seen as a strong absorption just below 3000 cm-1.

O
H3C

CH3

CH3

O
H3C

CH3
O

CH3

The above spectras are the expected NMR results for that of pure
isopentyl acetate. The H NMR spectroscopy shows a doublet with an
integration of six representing that of the terminal methyl groups which are
equivalent being split by a single hydrogen. Subsequently that hydrogen
shows up as a septet with an integration of one. The hydrogens of the alpha
carbon show up close to 4 ppm due to the high deshielding of the ester
group. In the C NMR we see the carbonyl carbon the furthest down field do
the electronegative oxygen of the ester. The shifts of the subsequent carbons
are shifted upfield in relation to their distance from the ester.

Citations

1) D.L. Pavia, G. M. Lampman, G. S. Kriz, and R. G. Engel Introduction to

Organic Laboratory Techniques: A Small Scale Approach, 3 rd Ed., (2011)
Brooks/Cole, pp.84-91
2) "Isopentyl Acetate." ChemicalBook---Chemical Search Engine. Chemical
Book, n.d. Web. 24 Oct. 2012.
<http://www.chemicalbook.com/ChemicalProductProperty_
EN_CB3158874.htm

3) D.L. Pavia, G. M. Lampman, G. S. Kriz, and R. G. Engel Introduction to

Organic Laboratory Techniques: A Small Scale Approach, 3 rd Ed., (2011)
Brooks/Cole, pp.861-959

Questions
1. Removal of water as it is formed will also direct the reaction to form the
product of the ester.
2. Sodium bicarbonate acts to neutralize the acid in the crude product.
3. The acetic acid reacts with the sodium bicarbonate to produce a salt,
water, and CO2 which is a gas.
4. The limiting reagent was determined to be the Isopentyl alcohol, while the
limiting reagent was acetic acid. The molar excess of acetic acid was about
2.6 times greater than Isopentyl alcohol.
7.
O
HO S

OH

O
H3C

O
H3C

OH

H3C

OH

CH3

H2O

CH3

CH3

H2O

OH

OH

OH

H3C

OH

H3C

OH

CH3
HO

OH

CH3

CH3

CH3

H3C

O
CH3

CH3

H2O

8. Because upon freezing it forms crystals that look like needles, due the
lack of water.

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