Synthesis of Oil of Wintergreen
uthor: Frank La Gatta
Date Created: August 1, 2007
Subject: Chemistry
Level: Honors Regents – tenth grade
Standards: 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:
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
Students will:
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
Vocabulary:
Isomers
Functional groups
Esterification
Extraction technique
Limited reagent
Percent yield
Materials:
For Each Pair:
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
Safety:
Goggles, gloves, apron
Work under fume hood
Do not breathe vapors of methanol and ether