Name ___________________________

Chapter 23

50

Date ___________________

Class __________________

Functional Groups

EXPERIMENT

ESTERS OF CARBOXYLIC ACIDS

PURPOSE
Text Reference
Section 23.3

To synthesize various esters from carboxylic acids and alcohols.

Time Required
40 minutes

BACKGROUND

Objectives
Observe several different
acid-catalyzed reactions
of carboxylic acids with
alcohols to form esters.
Describe the odor of the
ester products.

Did you know the aromas of bananas, strawberries, and other fruits are
the result of organic chemistry? Esters account for the distinctive odors
of many fruits. Many of these ester compounds have pleasant odors. You
can synthesize an ester in the lab by heating a carboxylic acid in an
alcohol solution containing a small amount of strong acid as a catalyst.
H

RCO2H  ROH 1 RCO2R  H2O

carboxylic acid alcohol
ester
water

Pearson Education, Inc., publishing as Pearson Prentice Hall. All rights reserved.

In this experiment, you will react carboxylic acids and alcohols, in the
presence of a strong acid catalyst, to form esters.

Advance Preparation
Caution: Concentrated
H2SO4 can react so
vigorously with organic
matter that explosions can
occur. To minimize this risk,
keep the quantity of 18M
H2SO4 at each lab station
very small. Do not dispense
in dropper bottles with
rubber bulbs. Caution
students to read all labels
carefully and never to add
water to the container of
18M H2SO4.

Demonstrate the technique

for wafting vapors toward the
nose. Students must not
attempt to taste esters!

MATERIALS (PER PAIR)

safety goggles
glass-marking pencil
5 medium test tubes
test-tube rack
10-mL graduated cylinder
dropper pipet
ring stand
ring support
2 250-mL beakers
wire gauze
gas burner
thermometer
90% methanoic acid,
HCOOH tfc

glacial ethanoic acid,

CH3COOH tfc
salicylic acid, C6H4OHCOOH t
methanol, CH3OH tf
ethanol, C2H5OH tf
2-methyl-1-propanol,
C4H9OH tf
1-pentanol, C5H11OH tf
1-octanol, C8H17OH tf
18M sulfuric acid, H2SO4 tc
ice
distilled water

SAFETY FIRST!
In this lab, concentrated H2SO4 is used to catalyze a chemical reaction. It
is strongly recommended that your teacher assist during this procedure.
Observe all precautions, especially the ones listed below. If you see a
safety icon beside a step in the Procedure, refer to the list below for its
meaning.
Caution: Wear your safety goggles. (All steps.)
Experiment 50 Esters of Carboxylic Acids 299

Name ___________________________
Some additional flavor esters
are as follows:

Date ___________________

Class __________________

Caution: All acids are corrosive, and several of the carboxylic

acids used in this experiment are concentrated and particularly
hazardous. (All steps.)

Name: ethyl methanoate

Formula: HCOOCH2CH3

Caution: The chemicals used in this experiment are toxic. Avoid

contact with these chemicals. (All steps .)

Odor/Flavor: rum
Name: ethyl butyrate

Caution: Alcohols are flammable liquids. Do not dispense these

compounds near an open flame. (Step 2.)

Formula:
CH3(CH2)2COOCH2CH3

Caution: Mix chemicals only according to directions. Never add

water to 18M sulfuric acid. Never add 18M sulfuric acid to any
other concentrated acid or to an alcohol.

Odor/Flavor: pineapples
Name: pentyl butyrate
Formula:

Note: Return or dispose of all materials according to the

instructions of your teacher. (Step 4.)

CH3(CH2)2COO(CH2)4CH3
Odor/Flavor: apricots
Name: methyl butyrate
Formula: CH3(CH2)2COOCH3
Odor/Flavor: apples

PROCEDURE
As you perform the experiment, record your observations in Data Table 1.
1. CAUTION: The acids used in this experiment are extremely
corrosive. Label five medium test tubes with the numbers 15.
Put the tubes in a test-tube rack. To each of the tubes, add 1 mL
of a carboxylic acid and 1 mL of an alcohol, as listed in Data
Table 1. In the case of the solid carboxylic acid, salicylic acid,
add 1 g of acid and 1 mL of alcohol to the tube.

Step 2.
Note: It is strongly
recommended that you add
the drops of 18M H2SO4.

Disposal 3: All reaction

solutions used in this
experiment.

300 Chemistry Laboratory Manual

3. Turn off the burner and remove the test tubes from the hot
water bath. Cool the tubes in an ice bath. Add 5 mL of distilled
water to each tube. Any ester produced in the reaction will float
on the water in the tube. Note the odor of the ester by wafting
the fumes toward your nose with your hand. Try to relate each
odor to a familiar fruit, flower, or vegetable. Record your
observations in Data Table 1.
4. Follow your teachers instructions for proper disposal of the
materials.

Pearson Education, Inc., publishing as Pearson Prentice Hall. All rights reserved.

Use the following disposal

method for chemical waste.

2. CAUTION: Keep containers of alcohols and carboxylic acids

away from flames. Add 35 drops of concentrated sulfuric acid
to each tube and heat the tubes in a water bath at 60C for
1015 minutes.

Name ___________________________

Date ___________________

Class __________________

OBSERVATIONS
DATA TABLE 1: RESULTS AND CONCLUSIONS
Test Tube

Carboxylic Acid

Alcohol

Ester Synthesized

Odor of Ester

methanoic acid

2-methyl-1-propanol

isobutyl methanoate

raspberries

glacial ethanoic acid

ethanol

ethyl ethanoate

ripe fruit

glacial ethanoic acid

1-pentanol

pentyl ethanoate

bananas

glacial ethanoic acid

1-octanol

octyl ethanoate

oranges

salicylic acid

methanol

methyl salicylate

oil of wintergreen

ANALYSES AND CONCLUSIONS

1. Complete Data Table 1 by naming the esters that were synthesized in the
experiment.
2. Write a general equation for the acid-catalyzed formation of an ester from an
alcohol and a carboxylic acid.
H
RCO2H  ROH 1 RCO2R  H2O

Pearson Education, Inc., publishing as Pearson Prentice Hall. All rights reserved.

3. Why was water added to the tube before you were asked to smell it? (Hint: What
was in the water layer in the test tube?) To answer this question, discuss the
relative solubility of acids, alcohols, and esters in water.
The esters are not soluble in water. The esters are also less dense
than water. As a result, upon addition of water, the esters float to the
surface of the test tube where they are exposed to the air. Their odor
is, thus, more obvious to the investigator.

4. Why were the reactions kept free of water during heating?

The reaction for the production of an ester is reversible:
acid  alcohol 1 ester  water
According to Le Chteliers principle, since water is a product of
the reaction, the addition of water will force the reaction to the left.
Thus, the yield of ester will decrease.

Experiment 50 Esters of Carboxylic Acids 301

Name ___________________________

Date ___________________

Class __________________

5. Write equations for each of the esterfication reactions in this experiment. Use
structural formulas in the equations and write the name of each compound below
its structural formula.
CH3

O
CH3
#
HCOOH CH3CHCH2OH 1 HC 2 O 2 CH2CHCH3  H2O
H

methanoic 2-methyl-1-propanol
acid
(isobutyl alcohol)

isobutyl formate

water

O
#
CH3COOH CH3CH2OH 1 CH3C 2 O 2 CH2CH3  H2O
H

ethanoic
acid

ethanol

ethyl ethanoate

water

O
#
CH3COOH CH3CH2CH2CH2CH2OH 1 CH3C 2 O 2 CH2CH2CH2CH2CH3  H2O
H

ethanoic
acid

1-pentanol

pentyl ethanoate

water

O
#
CH3COOH  CH3(CH2)6CH2OH 1 CH3C 2O2CH(CH2)6CH3  H2O
ethanoic
1-octanol
octyl ethanoate
water
acid
H

^
%

O
#
C 2 OH
 CH3OH

H

salicylic acid

methanol

 H2O
OH

oil of wintergreen

water

6. In esterfication reactions, the products are in chemical equilibrium with the

reactants. Suggest several ways of causing the equilibrium to shift in favor of the
production of additional ester.
The general equation for ester formation is:
H

R 2 CO2H  R 1 R 2 CO2R  H2O

One way to improve the yield of ester is to use a large excess of the alcohol. According to
Le Chteliers principle, the equilibrium will shift to use up as much of the excess alcohol as possible.
One way this can happen is by adding more carboxylic acid to make more ester. Another way
is to remove water, a product of the reaction. Removal of water forces more alcohol and acid
to react to produce more water and more ester in order to restore the equilibrium.

302 Chemistry Laboratory Manual

Pearson Education, Inc., publishing as Pearson Prentice Hall. All rights reserved.

OH

O
#
C 2 OCH3

Name ___________________________

Date ___________________

Class __________________

GOING FURTHER
Develop a Hypothesis
Based on the results of this lab, predict the product formed when
5-hydroxypentanoic acid is treated with acid catalyst.
#

HO

OH

H

O
Propose a mechanism for this reaction. How does the acid catalyze the reaction?
The acid catalyzes an intramolecular esterification to form a cyclic ester.

Design an Experiment

Pearson Education, Inc., publishing as Pearson Prentice Hall. All rights reserved.

Propose an experiment to test your idea(s). If resources are available and you have
your teachers permission, perform the experiment.

Experiment 50 Esters of Carboxylic Acids 303