EXPERIMENT 02
ESTERIFICATION
Background
Organic compounds are primarily composed of carbon and hydrogen atoms along with
heteroatoms such as oxygen, nitrogen, sulfur, and the halogens. Because of the vast number of
organic compounds that exist in nature and that can be synthesized in the laboratory, they are
placed in classes called functional groups depending on the structural features present in the
molecules. Some example of organic compounds and their functional groups are alcohols which
contain a hydroxyl (OH) group, and carboxylic acids which contain a carboxyl group (COOH).
When these two types of organic compounds react, they form an ester.
Esters are structurally characterized by the presence of a carbonyl group with an alkoxy
group attached to the carbonyl carbon. Esters are volatile substances that have lower boiling
points than alcohols and carboxylic acids. These compounds both occur naturally and are
synthesized in the laboratory as scents of flowers and fruits. In the laboratory, esters can be
synthesized from an alcohol and a carboxylic acid in the presence of an acid catalyst and heat
through the process of Fischer Esterification.
In this experiment, esters will be synthesized in test tubes from different alcohols and
carboxylic acids and characterized with a simple, chemical test involving phenolphthalein, a
common acid-base indicator.
Objectives
At the end ofthis activity, students will be able to
1. Synthesize esters from alcohols and carboxylic acids;
2. Describe the conditions required for the synthesis and hydrolysis of esters;
3. Observe the changes in the physical and chemical properties of alcohols,
carboxylic acids, as they are combined into esters; and
4. Distinguish alcohols, carboxylic acids, and esters based on their physical,
chemical, and structural properties
Reagents
● Isoamyl alcohol (Isopentyl alcohol)
● Ethanol
● Methanol
● Glacial Acetic Acid
● Salicylic Acid
● Concentrated sulfuric acid
Materials and Glassware
Material/Glassware Quantity
Beaker (500-mL) (250) 1
Beaker (100-mL) 1
Test tube holders (2) 1
Test tubes (4) 4
Additional materials needed that will be available in the laboratory room:
Stove
Part 1: Synthesis
1. Prepare a hot water bath by filling up a 500-mL halfway with tap water and placing
it on top of a stove.
2. Add 10 drops of alcohol, 10 drops (if liquid) or a pinch (if solid) of carboxylic acid
into a test tube.
3. Add 2 drops of concentrated sulfuric acid into the test tube with the alcohol and
carboxylic acid.
4. Place the test tube into the hot water bath for ten (10) minutes or until a scent is
detected coming from the test tube.
5. Transfer the test tube into a 100-mL beaker filled halfway with tap water to cool
down. Observe any changes in the appearance of the contents of the test tube.
6. After cooling, carefully waft the scent coming out of the test tube and describe the
scent.
Part 2: Characterization
1. Transfer the contents of the test tube from Part 1 into a 100-mL beaker
2. Add approximately 10mL distilled water to the same beaker
3. Swirl the contents of the 10mL beaker and dunk the contents into a nearby sink
4. Bring the beaker towards your face and gently waft the scent rising from the beaker
towards your nose
**Optional: You may try synthesizing esters from the assigned alcohols and
carboxylic acids of the other groups!
Data Sheet
Experiment 02
Esterification
Grp No.____ Section______
Date Performed___________ Date
Submitted__________
Name of groupmates Signatures
____________________________________ ______________
____________________________________ ______________
____________________________________ ______________
____________________________________ ______________
1. Assigned Alcohol
2. Assigned carboxylic acid
3. Observations during synthesis of ester
4. Describe the scent of the synthesized ester
Post Lab Report
Experiment 02
Esterification
Name:___________________________________ Section: _________ Class No. _______
Group No. ____________ Date Submitted___________________
1. Draw the structures of all the alcohols used in this experiment.
2. Draw the structures of all the carboxylic acids used in this experiment.
3. Arrange esters, carboxylic acids, and alcohols in increasing boiling point. What is the
reason behind the differences in the boiling points of these compounds?
Salicylic acid > Glacial Acetic acid > Isoamyl alcohol > Ethanol > Methanol > Ester
Because of the presence of Intramolecular hydrogen, bonding carboxylic acids have a higher
boiling point than alcohol. Ester molecules do not have a hydrogen atom immediately bonded to
an oxygen atom. Because of this, they are unable to form hydrogen bonds with one another
across the molecular distance that separates them and, as a result, their boiling points are
significantly lower than those their isomeric carboxylic acid counterparts.
