Jocelynn Brunelle

2/8/15
Chemistry
Brianna Balke

Ester Synthesis
Purpose
The purpose of this lab is to learn the process by which sweet smells are synthesized.

Introduction
Molecules determine the smell an object gives off. An example of a molecule for smell would be an
ester. An ester is a sweet smelling molecule. Every ester needs a form of alcohol and a caboxylic acid to work.
The alcohol molecule ends in -OH while the putrid carboxylic acid molecule ends with O=C-O-H( the double
bonded oxygen at the top of the C). The two groups react once sulfur is added to the mix. The -H from alcohol
is taken and the -OH from the acid is taken. That forms H2O. The remaining atoms then bond to form an ester
with O=C-O-C(the double bonded oxygen on top). This information can be used when putting an acid and an
alcohol together. Other groups include fishy (amine), minty (ketone), gasoline (alkanes), and alcohol (alcohol).
To predict the smell it depends on the order of the molecule as well as what is in it.

Procedure
Wintergreen:
1. Add 6 drops of methyl alcohol to the test tube that has salicylic acid pre-measured.
2. Gently agitate the mixture.
3. Add 1 drop of concentrated sulfuric acid (H2SO4).
4. Gently agitate the mixture.
5. Place the test tube in a beaker of hot water for 3 minutes.
6. Add 15 drops of water.
7. Carefully smell the mixture, and record the smell.
Grape:
1.
2.
3.
4.
5.
6.
7.

Add 6 drops of methyl alcohol to the test tube that has anthrallic acid pre-measured.
Gently agitate the mixture.
Add 1 drop of concentrated sulfuric acid (H2SO4).
Gently agitate the mixture.
Place the test tube in a beaker of hot water for 3 minutes.
Add 15 drops of water.
Carefully smell the mixture, and record the smell.

1.
2.
3.
4.
5.
6.
7.
8.

Add 6 drops of n-propyl alcohol to a clean test tube.

Add 6 drops of glacial acid.
Gently agitate the mixture.
Add 1 drop of concentrated sulfuric acid (H2SO4).
Gently agitate the mixture.
Place the test tube in a beaker of hot water for 3 minutes.
Add 20 drops of water.
Carefully smell the mixture, and record the smell.

Pear:

Banana:
1.
2.
3.
4.
5.
6.
7.
8.

Add 6 drops of isoamyl alcohol to a clean test tube.

Add 6 drops of glacial acetic acid.
Gently agitate the mixture.
Add 1 drop of concentrated sulfuric acid (H2SO4).
Gently agitate the mixture.
Place the test tube in a beaker of hot water for 3 minutes.
Add 20 drops of water.
Carefully smell the mixture, and record the smell.

1.
2.
3.
4.
5.
6.
7.
8.

Add 6 drops of octyl alcohol to a clean test tube.

Add 6 drops of glacial acetic acid.
Gently agitate the mixture.
Add 1 drop of concentrated sulfuric acid (H2SO4).
Gently agitate the mixture.
Place the test tube in a beaker of hot water for 3 minutes.
Add 20 drops of water.
Carefully smell the mixture, and record the smell.

Orange:

Pineapple:
1.
2.
3.
4.
5.
6.
7.
8.
9.
Strawberry:
1.
acid.
2.
3.
4.
5.
6.
7.
8.
9.

This reaction takes place in a fume hood because of a smelly compound called butyric acid
Add 6 drops of n-butyl alcohol to a clean test tube.
Add 6 drops of butyric acid.
Gently agitate the mixture.
Add 1 drop of concentrated sulfuric acid (H2SO4).
Gently agitate the mixture.
Place the test tube in a beaker of hot water for 3 minutes.
Add 20 drops of water.
Carefully smell the mixture, and record the smell.
This reaction must take place in a fume hood because it uses a smelly compound called butyric
Add 6 drops of ethyl alcohol to a clean test tube.
Add 6 drops of butyric acid.
Gently agitate the mixture.
Add 1 drop of concentrated sulfuric acid (H2SO4).
Gently agitate the mixture.
Place the test tube in a beaker of hot water for 3 minutes.
Add 20 drops of water.
Carefully smell the mixture, and record the smell.

Apple:
1.
acid.
2.
3.
4.
5.

This reaction must take place in a fume hood because it uses a smelly compound called butyric
Add 6 drops of methyl alcohol to a clean test tube.
add 6 drops of butyric acid.
Gently agitate the mixture.
Add 1 drop of concentrated sulfuric acid(H2SO4).

6.
7.
8.
9.

Gently agitate the mixture.

Place the test tube in a beaker of hot water for 3 minutes.
Add 20 drops of water.
Carefully smell the mixture, and record the smell.

Results
REACTANTS
Alcohol

Carboxylic Acid

Salicyclic Acid

PRODUCT

FLAVOR

Ester

Intended

Methyl Salicylate

Methyl Alcohol
Wintergreen

Methyl

Anthranilic Acid

Methyl Anthranilate

Grape

n-Propyl

Acetic Acid

n-Propyl Acetate
Pear

Isoamyl

Acetic Acid

Isoamyl Acetate
Banana

Observed

Octyl

Acetic Acid

Octyl Acetate
Orange

n-Butyl

Butyric Acid

n-Butyl Butyrate
Pineapple

Ethyl

Butyric Acid

Ethyl Butyrate
Strawberry

Methyl

Butyric Acid

Methyl Butyrate
Apple

Analysis of Results
Part 1: Reactions
Part 2: Questions
1. What evidence do you have that an ester was produced in each of your reactions?
Evidence for whether or not an ester was created lies in the smell the chemicals gave off and the
structure of the chemical. Esters give off a sweet smell and so did all of the results except for the first one.
Esters also have O=C-O-C in the middle of the chemical structure which all of the reactions have.
2. What is the role of sulfuric acid in this reaction? How come it isnt listed with the other
reactants?
Sulfuric acids role in the reaction is the catalyst. It doesnt get listed with the other reactants because it
makes the reactants react faster. Sulfuric acid is what makes the products.

3. If you wanted to synthesize a molecule that had the sweet smell of cinnamon (pictured below),
what would you do? What ingredients would you mix? (Draw them.) What reaction would take place?
4.
I would first draw the reactants would look like and then determine what chemicals were involved.

Ethyl Cinnamate

Conclusion
In your own words, describe what happens at a molecular level when an ester synthesis reaction takes place.
When an ester synthesis reaction takes place the alcohol and the carboxylic lose their end, which becomes water,
and come together to form an ester using sulfur to speed up the process. An oxygen and a hydrogen come from the acid
and an oxygen comes from the alcohol to form the H2O. The remaining atoms then form the ester and have a double
bonded oxygen to a carbon, another oxygen and a carbon in the middle(O=C-O-C).

Appendix: Skeletal Structures for Alcohols and Carboxylic Acids Used in this Lab
Alcohol

Carboxylic Acid

Methyl

Salicylic Acid

n-Propyl

Isoamyl

Octyl

Anthranilic Acid

n-Butyl

Acetic Acid

Ethyl

Butyric Acid