Jordan Vieira

Feb 23, 2016

Chemistry
Emily Berman

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

Introduction
Smell is a part of science and it is a part of chemistry. You can predict the smell of certain substances using
certain characteristic's. Those characteristics include name, formula, structure, and functional group. If the smell
is fishy then it is part of the functional group amine and it will have one nitrogen and the name will end in
amine. If the smell is minty then its functional group is ketones and its structure is a ring. Also, its name ends in
one. If you have a sweet smell then its functional group is esters and its structure has a double bonded oxygen
and its formula has 2x as many Hydrogen as Carbon. Also, its name ends in ate and yl. Another smell is
putrid and its functional group is carboxylic acid, its structure has a double bond to oxygen and a bond to both
carbon and hydrogen. Its formula has 2 oxygen atoms, and 2x as many hydrogen as carbon, and the name ends
in acid. The next smell is gasoline. Its functional group is alkanes and the structure is ---------, for the formula it
has no oxygen, and its name ends in ane. These are all the characteristics to smell.

Procedure (Fill in where instructions are missing)

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 anthranlic 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.

Add 6 drops of n-propyl alcohol to the test tube that has glacial acetic 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 20 drops of water.
Carefully smell the mixture, and record the smell.

Pear:

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

Add 6 drops of isoamyl alcohol to the test tube that has glacial acetic 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 20 drops of water.
Carefully smell the mixture, and record the smell.

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

Add 6 drops of octyl alcohol to the test tube that has glacial acetic 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 20 drops of water.
Carefully smell the mixture, and record the smell.

Orange:

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

This reaction must take place in a fume hood because it uses a smelly compound called butyric
Add 6 drops of n-butyl alcohol to the test tube that has butyric 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 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 the test tube that has butyric 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 20 drops of water.
Carefully smell the mixture, and record the smell.

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

This reaction must take place in a fume hood because it uses a smelly compound called butyric.
Add 6 drops of methyl alcohol to the test tube that has butyric 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 20 drops of water.
Carefully smell the mixture, and record the smell.

Results
Attach the page that looks like this (filled out):
REACTANTS
Carboxylic Acid

Alcohol

PRODUCT
Ester

Salicyclic Acid

Methyl Alcohol

Methyl Salicylate

FLAVOR
Intended

Observed

Wintergreen

Grape

Pear

Analysis of Results
Part 1: Reactions
Draw the full reaction for each of the Ester synthesis reactions you performed. You may choose to use either
Lewis structures or skeletal structures. I suggest you leave a blank page in your lab report and draw these in by
hand.
*See appendix at the back of the lab for the skeletal structures of the different acids and alcohols we used.
Part 2: Questions
Answer the questions below:
1. How I know that an ester was produced in each of the reactions was because there was a
different reaction for each ester. Also, there are both H and HO atoms being taken away to form the
actual ester. Evidence that proves this is the pear flavor. This evidence shows that due to the carboxylic
acid and the alcohol wanting to mix together they both form an ester in which a H bond and an HO
bond is being taken away to form a full ester.
2. The role of Sulfuric acid in this lab was to help speed reaction which formed the ester. The
reason for why it isnt listed with the other reactants is because Sulfuric acid is not a reactant. It is a
source that just helps to speed the reaction time which helps the ester have a much faster reactant.
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?
(HINT: Look at the picture of the product and try to walk yourself backwards through the reaction to get
your reactants)

Ethyl Cinnamate

Conclusion
In conclusion, at a molecular level when an ester synthesis reaction takes place a carboxylic acid is being
treated with an alcohol substance. Due to the mixture of the two reactants, this then causes water (H2O) to be
released from the process as it was forming. Also, concentrated sulfuric acid helped to speed the reaction which
helped to form a stronger ester. This whole process causes a bond between the two reactants which were
carboxylic acid and alcohol which helps form the ester synthesis.

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

Carboxylic Acid

Methyl

Salicylic Acid

n-Propyl

Anthranilic Acid

Isoamyl
Octyl

n-Butyl

Acetic Acid

Ethyl

Butyric Acid