Name: ___________________________ Date: ____________________ Lab Partner =__________________

The Preparation of Fragrant Esters

“Perfume is the key to our memories” - Kate Lord Brown

Learning Goal

Esters are the product of reaction of an organic (carboxylic acid) with an alcohol. Many esters are components of the
essential oils of flowers and fruits and are responsible for the “fruity” odours and flavours of many naturally occurring
products. Chemists can reproduce these odours or flavours in the lab by mixing the right alcohol and carboxylic acid
together; thus, producing “artificial” or “synthetic” versions of these naturally occurring compounds. In this lab activity you
will create a number of different esters and attempt to identify the odour of each ester created.

Introduction

When an organic carboxylic acid, R-COOH, is heated with an alcohol, R’-OH, in the presence of a strong mineral
acid, the chief organic product is a member of the family of organic compounds known as esters.

The general reaction for the esterification of an organic acid with an alcohol is
O O
H2SO4
+ R' OH + H2O
R'
R OH Cat. R O

Acid Alcohol Ester

* Where R = alkyl group

Esterification is an equilibrium reaction, which means that the reaction does not go to completion on its own.
Frequently, however, the esters produced are extremely volatile and can be removed from the system by distillation. If the
ester is not very easily distilled, it may be possible instead to add a desiccant to the equilibrium system, thereby removing
water from the system and forcing the equilibrium to the right.Unlike many organic chemical compounds, esters often have
very pleasant, fruitlike odors. Many of the odors and flavorings of fruits and flowers are due to the presence of esters in the
essential oils of these materials.

The esterification reactions shown above are actually equilibrium processes and can be reversed. The reverse of
the esterification reaction is referred to as a hydrolysis reaction, because it represents the breakdown of the organic
compound through the action of water.

R-CO-OR’ + H2O  R-COOH + HO-R’

Generally a fruit or flower may contain only a tiny amount of ester, giving a very subtle odor. Usually, the ester is part of
some complex mixture of substances, which, taken as a whole, have the aroma attributed to the material. When prepared
in the laboratory in relatively large amounts, the ester may seem to have a pronounced “chemical odor, and it may be difficult
to recognize the fruit or flower that has this aroma.

Safety Precautions

 Safety eyewear, goggles, must be worn at all times while you are in the laboratory,
whether or not you are working on an experiment.
 Most of the organic compounds used or produced in this experiment are highly
flammable. All heating will be done using a hotplate, and no flames will be
permitted in the laboratory.
 Sulfuric acid is used as the catalyst for the esterification reactions. Sulfuric acid is
dangerous and can burn skin, eyes, and clothing very badly. If it is spilled, wash immediately before the acid
has a chance to cause a burn, and inform the instructor. Wear gloves to protect hands.
 The vapors of the esters produced in this experiment may be harmful. When determining the odors of the
esters produced in the experiment, do not deeply inhale the vapors. Merely waft a small amount of vapor from
the ester toward your nose.
Materials:

 Salicylic acid  Test tube holder

 Glacial acetic acid  Test tubes (6)
 Pentanol  Hot plate
 Methanol  Stirring rods
 Sulfuric acid  Droppers
 Octanol  Graduated cylinders
 Ethanol  Tape for labelling
 250 mL beaker

Procedure
1) Set up a 250 mL beaker, half full with water, on a hot plate to act as a hot bath (75o-80oC). Do not
allow water to boil. See diagram below for the set up.

2) Obtain two clean test tubes. Into one test tube add approximately 2mL of the desired alcohol; into the
second test tube add approximately 2mL of the desired carboxylic acid. Note: of the reactant is a solid
use 1 g of substance. Carefully, waft the vapours of each tube towards your nose and record the odour
of each reactant. Following this for each reaction.

Test Tube # Alcohol Carboxylic Acid

1 Pentan-1-ol Salicylic acid
2 Pentan-1-ol Glacial acetic acid
3 Octan-1-ol Glacial acetic acid
4 Methanol Salicylic acid
5 ethanol Glacial acetic acid

3) Mix the contents of the two test tubes together. Using a dropper add 5 drops of concentrated sulphuric
acid to the mixture. Carefully, mix the solution.
4) Place the test tube containing the reactants into the hot bath for about 5 minutes. Do not let the water
or the contents of the test tube boil.
5) Remove the test tube from the water bath and carefully waft the vapours towards your nose. If you
have trouble detecting the odour of the ester follow the next step.
6) Add approximately 20mL of warm water to a 250mL beaker. Pour the contents of your test tube into
the beaker containing warm water.* Carefully, waft the vapours towards your nose and smell the odour
emanating from the beaker.
7) Name the ester and describe its odour.
8) Discard the contents of your beaker into the organic waste jar found in the fumehood. Clean station.
Observations

Test Tube Alcohol Alcohol Organic Organic Ester Fragrance

Name amount Acid Name Acid Name Produced
used (mL) amount
(mL, g)
1

Analysis
1. Why was sulfuric acid used in this reaction? (1)
2. Use your knowledge of chemistry to write a chemical reactions for the esters you made in each
test tube. Sample table found below. (10)
Test Tube Number Reaction
1
2
3
4
5

3. Explain why the synthesized esters do not always match the odour of the fragrance found in
nature. (1)
4. Describe any sources of error that would have occurred during this lab experiment. (3)
 Success Criteria – Formal Esterification of Fragrances Lab Report
Student Name: ______________________ Partner(s): ______________
CONTENT - KNOWLEDGE
Criteria Mark Total Mark
Title Page (5 marks)
Abstract – ½ page (5 marks)
____
Introduction – ½ page (5 marks)
22
Materials List (2 marks)

Procedure (5 marks)

CONTENT - APPLICATION
Criteria Mark Total Mark
Observations (10 marks)

Analysis Questions (15 marks)

#1 – 1 mark ____
#2 – 10 marks
#3 – 1 mark
25
#4 – 3 marks

PRESENTATION - COMMUNICATION
Criteria Mark Total Mark
Conclusion – 1 paragraph (3 marks)

Discussion – ½ page (5 marks)

__
8
PRESENTATION - THINKING
Criteria Mark Total Mark

Pre-Lab (10 marks)

Rough Copy of Lab (2 marks)

__
15
References (3 marks)

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