Synthesis of Oil of Wintergreen

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Frank La Gatta
August 1, 2007
Chemistry
Honors Regents tenth grade
Isomers of organic compounds have the same molecular formula, but
different structures and properties
Organic acids, alcohols, esters, aldehydes, ketones, ethers, halides,
amines, amides, and amino acids are types of organic compounds
that differ in their structures
Functional groups impart distinctive physical and chemical properties
to organic compounds
Real World Connections: types, varieties, uses of organic compounds,
organic isomers, odors, cosmetics, dyes
Skills: classify an organic compound based on its structural or
condensed formula
Draw a structural formula with a functional group(s) on a straight chain
hydrocarbon backbone when given the correct IUPAC name for the
compound
Schedule: Lab Activity: 45 minutes
Cooperative learning activity- two 45 minute periods

Objectives:

Vocabulary:

To synthesize methyl salicylate by

esterification of acetylsalicylic with methanol
To separate the synthesized methyl
salicylate by the extraction technique
To construct and name organic molecules:
mainly isomer structures
To determine the differences in isomers

Isomers
Functional groups
Esterification

Students will:

molecular model kits (Organic molecule

cooperative learning activity)
two aspirins
5 ml of methanol
4 drops of concentrated sulfuric acid
sodium bicarbonate is used until fizzing with
salicylic acid stops
ether use in small quantity
mortar and pestle
two scintillation vials
one pipette
graduated cylinder
hot plate

Construct various isomer structures by

manipulating molecular model kits
Use the IUPAC system to name isomers
Classify isomers based on their physical
and chemical properties
Connect real world chemistry to isomers
Synthesize oil of wintergreen
Use an extraction technique to remove the
product made
Use quantitative skills to determine the
number of moles of salicylic acid and
methanol from the number of grams
measured in the beginning of the lab
Determine the limited reagent in the
esterification reaction
Determine the percent yield of product
obtained
Identify the functional groups in the

Extraction technique
Limited reagent
Percent yield

Materials:
For Each Pair:

Safety:
Goggles, gloves, apron
Work under fume hood
Do not breathe vapors of methanol and ether

reaction
Determine the two additional byproducts
produced in the synthesis of methyl
salicylate
Determine the purpose of the extraction
technique in the lab activity

Handle concentrated sulfuric acid with care - If

spilled on your skin wash immediately with
plenty of water
If safety issues are a concern this lab could
easily be used as a teacher demonstration

Science Content for the Teacher:

Isomers are compounds that have the same molecular formula but different structural
formulas; therefore different physical and chemical properties.
IUPAC rules for nomenclature of organic compounds
Esterification reaction- carboxylic acid reacts with an alcohol in the presence of sulfuric
acid to produce an ester.
Functional groups and their importance in organic chemistry (OH alcohol, COOH
carboxylic acid, COO ester) for the esterification reaction
To be able to find mass and understand the conversion of grams to moles
Limited reagent is the reactant that is used up in the reaction and the other reactant is in
excess
Percent yield = actual/ theoretical x 100 %
Extraction is the technique used to obtain your product form the sample
Preparation:
Print student copies for the lab on the synthesis of wintergreen
Set up for the lab (look at materials needed)
Lab set up takes about 30 minutes
Print copies for activity for organic molecules ( molecular model kits needed)
Classroom Procedure:
Engage (Time: 45 min.)
Students will use molecular model kits to construct organic molecules. They will use
these models to help them in the nomenclature of organic molecules. Students will use
the provided worksheet on organic molecules. This will begin students to observe that
various isomers constructed from one given structure have different physical and
chemical properties.
Explore (Time: 45 min.)
Lab activity on the production of wintergreen. Students will understand the purpose of
functional groups in chemical reactions. Students will once again reinforce nomenclature
of organic molecules. Students will determine the purpose of sulfuric acid in the
esterification lab. Students will write the esterification reaction for the synthesis of
wintergreen.
Explain (Time: 45 min.)
Synthesis of Oil of Wintergreen
-2

Teacher will explain change of structure change of smell ( use power point
presentation). The discussion will focus on isomers, nomenclature and properties of
isomers, interconversion of functional groups, the meaning of oxidation and reduction
from the previous unit in Redox and its relationship in chemical reactions in changing
structure changing smell.
Expand (Time)
Discuss real world connections/ odors, flavorings, cosmetics, dyes in Organic Chemistry.
Loop information from other concepts taught in previous units: mole conversion that is
needed for question 1 in the lab activity. Students will connect the concept of limited
reagent with the lab on production of wintergreen (Stoichiometry Unit). Students will
connect a neutralization reaction from the unit on Acid and Bases. Catalysts concept from
Kinetics unit can be integrated in the use of sulfuric acid. Covalent bonding, the number
of bonds carbon can form in a structure to help students logically draw structures. Carbon
forms four bonds.
Assessment:
Students are assessed by the written lab reports they hand in and their class participation.
Completing the lab activity sheet and related activities accurately also serves as an
assessment.
Extension Activities:
Students can choose a particular isomer and draw as many structures possible and discuss
their physical and chemical properties.
Supplemental Information:
Advanced students can be exposed to chiral centers and chirality of molecules.
Handedness also plays a role in organic chemistry due to the tetrahedral formation of
hybridized carbon. Most drugs and most molecules in our bodies are handed. Discuss
enantiomers and their properties. One important concept is that different enantiomers of
chiral compounds often taste and smell different. This correlates nicely with the power
point presentation.

References:
Textbook: Modern Chemistry, Holt, 1999 version is a great book for Chemistry Honors.
Wikipedia has some valuable information on chirality, and enantiomers, and handedness.
Organic Chemistry, McMurry, Cornell University

Synthesis of Oil of Wintergreen

-3

ORGANIC MOLECULES ACTIVITY

Organic chemistry is the study of carbon and its carbon compounds. The number of
organic compounds is vast in nature. Organic molecules are predominantly found in all
organisms.
Carbon has the ability to form covalent bonds not only with other kinds of atoms, but
also with other carbon atoms. The ability of carbon to form chains, rings, and networks
constitutes is responsible for the numerous number of organic compounds. Not only are
carbon atoms linked by single covalent bonds, but they are sometimes linked by double
or triple covalent bonds.
Carbon atoms represented by a specific molecular formula may be arranged in several
different ways, which creates compounds with different properties and structures.
Compounds that have the same molecular formula but different structures are called
isomers. A structural formula indicates the exact number and types of atoms present in a
molecule and also shows how atoms are bonded to each other. The various isomers with
a specific molecular formula are referred to as structural isomers.

C4H10

H
H

H
H

C
H

H
C

H
C

n- butane

H
H

isobutene

Materials: Molecular Model kits

Procedure: Construct the models of the compounds listed below using the following key:

black - carbon

green- chlorine

yellow- hydrogen

orange (or purple)- bromine

2. Draw the molecular structure and properly name each of the compounds.

a) CH4

_________________

b) CH3Cl

________________

c) C2H6

_______________________

d) C2H5Br
_________________

e) C3H8

________________

(f) Replace one of the hydrogens from compound (e) with a bromine atom and draw
and name the two possible structures.

________________________________

_______________________________

(g) Draw and name two isomers of C4H10:

____________________________

____________________________

(h) Draw and name three isomers of C5H12:

___________________________________________

__________________________________________

________________________________

Alkenes:
(i) C2H6
_____________

(j) C3H6

_______________

(k) Draw and name three isomers of C4H8:

________________________

_______________________

_____________________________

Alkynes:

(l) C2H2
_________________

(m) C3H4

___________________

(n) Draw and name two isomers of C4H10

___________________________

_____________________________

(O) Draw and name three isomers of C5H12

____________________________

___________________________

_______________________________

Conclusion:
1. What type of carbon bonds are found in the following?
Alkanes ____________

Alkenes______________

Alkynes _____________

2. Make a table listing the homologous series (alkane, alkene, alkyne ) that have up to
six carbon atoms. Include the general formula for each hydrocarbon family and list
the characteristics of each distinct family.

3. List four major characteristics of organic molecules:

1.
2.
3.
4.

4. Identify and discuss in detail the physical and chemical properties for the
three isomers of C5H12.
5.

What connections do the isomers of C5H12 have in the real world of

science?

6. Which of the following objects are chiral?

a) A basketball e) A monkey wrench
b) A fork
f) A snowflake
c) A wine glass
d) A golf ball

10

:
7. Draw the following compounds:
a) 2, 4- Dimethylheptane
b) 5- Ethyl- 3, 3- Dimethylheptane
c) cis- 1,4- Dichlorocyclohexane
d) 4, 5- Dimethyl 2, 6- octadyne
b) Which of the above compounds are chiral?
c) Label the chirality centers for the compounds that are chiral.
8. Draw the chiral molecules that meet the following description:
a) a chloroalkane, C5H11Cl c) an alcohol, C6H14O
b) an alkene, C6H12

d) an alkane, C8H18

11

Synthesis of Oil of Wintergreen

Pre- Lab Discussion: Methyl salicylate C6H4 ( HO) COOCH3, also known as salicylic
acid methyl ester, oil of wintergreen, is a natural product of many species of plants.
Methyl salicylate may be used by plants as a pheromone to warn other plants of
pathogens such as tobacco mosaic virus. Methyl salicylate is used in deep heating
liniments and in small amounts as a flavoring agent. Oil of wintergreen is used in the
field of medicine in aromatherapy.
Reaction:
O

H3C

H3C
OH

OH

H2SO4
H3C

Aspirin
(Acetylsalicylic Acid)

OH

Oil of Wintergreen
(Methyl Salicylate)

Objectives: To synthesize methyl salicylate by esterification of acetylsalicylic acid with

methanol.
To separate the synthesized methyl salicylate
Materials:

Bottle of aspirin, methanol, concentrated sulfuric acid, sodium bicarbonate,

Ether, mortar and pestle, scintillation vials, pipettes, graduate cylinder, hot
plate.

Safety:

Always wear goggles and gloves

Work under fume hood
Do not breathe vapors of methanol and ether
Handle concentrated sulfuric acid with care. If spilled on your skin wash
immediately with plenty of water.

Procedure:

1. Weigh two tablets of aspirin on the analytical balance scale to 0.01 gram.
2. Place in mortar and decompose the aspirin to a powder form.
3. Pour the powder aspirin into a scintillation vial. Add 5 ml of methanol.
4. Add 4 drops of concentrated sulfuric acid to the bottle. Gently swirl so
the contents are thoroughly mixed. Be careful the reaction is
exothermic.
5. Gently warm on hot plate for approximately 5 minutes.
6. Cool down and then neutralize the salicylic acid with sodium
bicarbonate. Add one drop at a time until the reaction stops fizzing.

Extraction: Use ether (or any other solvent available)

Do several extractions to remove by products
For each extraction two layers form. The top layer
is ether and the bottom layer is water/ methanol
Remove top layer with pipette .
Continue to evaporate the ether by a water bath in the fume
hood. After evaporation the smell of methyl salicylate is
produced .

Conclusion: 1. How many moles of salicylic acid and methanol are used in this
experiment?
2. Draw the two functional groups found in esters?
3. What is the purpose of concentrated sulfuric acid in an esterification
reaction?
4. Write the neutralization reaction between sulfuric acid and sodium
bicarbonate
5. Which substance is the limited reagent in the esterification reaction?
Explain!
6a. What is the percent yield of methyl salicylate?
b. Why is the percent yield of the product either too high or low ?
7. What are the two additional byproducts produced in the
synthesis of methyl salicylate?
8. What is the purpose of the extraction technique in this lab?