Chima Nwakpuda

TA: Alex Koval

Date Performed in Lab: March 20, 2015

Due Date of Report: March 27, 2015

Experiment 8B: Esterification Reaction - Isopentyl Acetate, and the use of Acidic Resins
Objective: This experiment explores the classic reactions of carboxylic acids with alcohols,
in the presence of acid catalyst, to yield esters with the addition of water. In the lab the
physical properties of these esterification products are examined and the technique of gas
chromatography was applied to the purification of these materials. The alcohol used in this
reaction was isopentyl alcohol with the carboxylic acid acetic acid in the presence of acid
catalyst sulfuric acid.
Experimental Procedure: The procedure was followed as described in Mayo, pages 201202, with the following modifications:
Reagents and Equipment
The reaction was set up on a scale of X what is described in the lab textbook.
A 5.0-mL conical vial was still used.
Substituted Drierite for calcium chloride in the drying tube.
Reaction Conditions
Did not stop the spin vane while the reaction mixture was cooling to room temperature.
Raised the vial out of the sand bath to begin cooling, but not so high that the spin vane
stopped rotating
Did not cut the amount of diethyl ether in half, but added the full 0.5 mL.
When removing the spin vane with forceps or a wand magnet, used the diethyl ether (0.5
mL) to rinse the spin vane (any product remaining on the spin vane was then washed back
into the Reaction vial).
Isolation of Product
Continued on a scale of X what is described in the lab textbook and cut in half all workup
Amounts.
Did not distill product. Transferred dried ether solution containing the product to
A tared, screw-cap test tube.
Concentrated the crude product solution as usual. Obtained the product weight.
Purification and Characterization
The crude product was analyzed by gas chromatography.
Chemical Tests
Omit this step.
Reaction Scheme:

Data and Results:

Compound

Molecular Formula

MW

Amount

mmol

bp(C)

Isopentyl Alcohol

C5H12O

88.15

400 uL

3.7

132

0.81

Acetic Acid

C2H4O2

60.1

750 uL

13.1.

116

1.05

Sulfuric Acid, concd

H2SO4

Product: Isopentyl acetate

C7H14O2

3.2

142

0.88

2 drops
130.19

416 mg

Observations:
Isopentyl alcohol + Acetic Acid + Sulfuric Acid was a brown solution.
The reaction produced a pleasant odor.
Solution was heated for an hour at a temperature of 160-180 degrees Celsius.
Addition of 5% NaHCO3 created two layers - top layer was yellow, bottom layer was
clear.
Silica gel was white solid.
The product was a light yellow liquid.
Calculations:
1) Theoretical Yield
(Limiting reagent) x (1/Molecular weight of limiting reagent) x (stoichiometry ratio) x (MW of
Isopentyl acetate) or (mmol of limiting reagent) x (stoichiometry ratio) x (MW of Isopentyl
acetate)

( 3.7 mmol of iosopentyl alcohol) x (1/1 ratio) (130.19 g/mol of Isopentyl acetate) = .48
mg of Isopentyl acetate

2) Yield of isopentyl acetate

(Test tube + boiling stone + product) (Test tube + boiling stone) = Crude Product

(11.981 g) (11.565 g) = .416 g or 416 mg of crude product

3) Percent Yield of isopentyl acetate

(Actual yield/theoretical yield x 100) = percent yield

(.416g) / (.48g) x 100 = 86.6 % yield

4) GC Retention Time
(Peak from the distance between the zero point line and the top of the peak) x (1min/cm)

Peak 1
1.1 cm x (1min/cm) = 1.1 min retention time
Peak 2
2.9 cm x (1min/cm) = 2.9 min retention time
Peak 3
5.4cm x (1min/cm) = 5.4 min retention time
5) GC Peak Area
(Height of the peak (in mm) x (Width at half height (in mm)
Peak 1

2.2 cm x .1cm = .22 cm = 22 mm^2 peak area

Peak 2
.2cm x .1cm = .02 cm = 2 mm^2 peak area
Peak 3
6.9cm x .4cm = 2.76 cm = 276 mm^2 peak area

6) GC Peak Identity
Peak 1 = acetic acid
Peak 2 = Isopentyl alcohol
Peak 3 = Isopentyl acetate

Questions:
1)

2) An explanation for the order of my elution is that the ester had the greatest retention time
meaning that it took the longest for this compound to travel from the injection point to the
detector because it had the highest boiling point so it can be seen as peak three. The
alcohol which had the second highest boiling point was peak two. Finally the acetic acid
which had the lowest boiling point was peak one because it traveled the fastest from the
injection point to the detector.
3) The peak areas for acetic acid, isopentyl alcohol, and isopentyl acetate were 22 mm2, 2
mm2, and 276 mm2 respectively. The combined area of the peaks is 300 mm2. The purity
of the crude product ester would be (276 mm2 / 300 mm2) x 100 which is equal to 92.0%
purity.
4) a) A large excess of acetic acid used in this fischer esterification was used to drive the
reactants to the products. Without an excess amount the reaction would be around the
equilibrium and wouldn't favor complete formation of the product which was our goal.
b) When acetic acid was used in excess for this reaction it was easily separated from the
product during the work up because when separating the aqueous layer and the organic
layer, the acetic acid stays in the aqueous layer while the isopentyl acetate product stays in
the organic layer. Isolating the product was simply a matter of separating the two layers.
However, if an excess of isopentyl alcohol were used instead, it would be much harder to
separate the alcohol from the product because both would remain in the organic layer
together. The alcohol would not be neutralized by the NaHCO3 and would stay in the
organic layer.
Works Cited:
1.Mayo, D. W.; Pike, R.M.; Forbes, D.C. Microscale Organic Laboratory with Multistep and
Multiscale Synthesis, 5th ed.; John Wiley & Sons, Inc., 2011; pp. 188-202.
2.Modifications for Expt: 8B Esterification Reaction - Isopentyl Acetate, Blackboard
document.
3. Boiling Point and MW of Isopentyl Acetate: http://en.wikipedia.org/wiki/Isoamyl_acetate