Chemistry

Chapter 6
Esters of Carboxylic Acids
Lab

Esters are a type of organic compound with a general molecular formula R—CO2R’.
Many of these compounds have pleasant odors. It is esters that account for the distinctive
odors of many fruits, such as bananas, pineapples, and oranges. Esters are synthesized in
the laboratory by permitting a carboxylic acid to react with an alcohol. This general
reaction is depicted below. A strong acid is needed to catalyze the reaction.

R—CO2H + R’—OH -------------- R—CO2R’ + H2O

Carboxylic alcohol ------------ ester water
Acid

R is a symbol that represents what is called a functional group. A functional group is the
portion of a molecule that is active in a chemical reaction and that determines the
properties of many organic compounds. Some examples of common functional groups
are found in the table below

Classes of Organic Compounds, Their Functional Groups, and General

Formulas
Class Functional Group General Formula
Alchohol --OH R -- OH
Ether --O-- R—O—R’
Aldehyde O O

--C—H R—C--H
Carboxylic Acid O O

--C—OH R—C—OH
Ester O O

--C—O-- R--C—O—R’

In esterfication reactions, the products are in chemical equilibrium with the reactants.
The reactions seldom go to completion unless the watr produced in the reaction is
removed as it forms. This will drive the reaction toward the products, according to
LeChatelier’s principle.

In this experiment, you will react a carboxylic acid and an alcholhol, in the presence of a
strong acid to form an ester.
Objectives: The point of this lab is to produce esters from carboxylic acids and
alcohols. It is also understand the use of structural formulas to represent compounds and
chemical reactions.

Equipment:
Medium test tubes wire gauze
Test tube rack burner
Ring stand dropper pipet
Ring thermometer
250 mL beaker 10 mL graduated cylinder

Materials:
Methanol 90% formic acid
Ethanol glacial acetic acid
2-methyl-1-propanol salicylic acid
1phentanol 18M sulfuric acid
1-octanol

Safety:
1)Goggles
2)aprons
3)acids
4)alcohols
5)mix only as directed.

Proedures:
Record your observations in a table below.
1)Label 5 test tubes 1-5. To each of the tubes add 1 mL of a carboxylic acid and 1 mL of
an alcohol as listed in the table below. Note: In the case of the solid carboxylic acid,
salicylic acid, add 1 g of acid and 1 mL of alcohol to the tube.

2)Add 3-5 drops of concentrated sulfuric acid to each tube and heat the tubes in a water
bath at 60oC for 10 to 15 minutes. We will do this using hot plates.

3)Remove the HOT test tubes from the water bath and carefully cool them in a stream of
cold tap water. Add 5 mL of distilled water to each tube. The ester produced in the
reaction will form a layer on top of the warer 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
odor of an animal, fruit, or vegetable. Record your observations below.

4)Discard the contents of the test tubes into the sink and flush with copious amounts of
water.
 Esters Synthesized from Carboxylic Acids and Alcohols
Carboxylic Acid Alcohol Ester formed Odor of Ester
Formic acid 2-methyl-1-
propanol
(isobutyl alcohol)

Acetic Acid ethanol

Acetic Acid 1-pentanol

Acetic Acid 1-octanol

Salicylic Acid methanol

Results and Conclusions

1)Complete the table above by naming the esters that were synthesized in the experiment.
(check out the extension on the last page for a hint on this)
2)Why were the reactions kept free of water during heating?

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?) discuss the relative solubility of acids, alcohols, and
esters in water in order to answer this question.
Extension:
Write equations for each of the esterification reactions in this experiment. Use structural
formulas in the equations and write the name of each compound below its structural
formula.

Example:

Formic Acid + 2-methyl-1-propanol ----------- isobutyl formate and water

(isobutyl alcohol)