WCATY 2001
Explorations at UW-LaCrosse: Science and Medicine
February 17, 2001
This page is under construction. Check back periodically. Additional descriptions and links may appear.
In this workshop we will carry out chemical syntheses of two medicinal
compounds using college-level procedures and equipment. We will make
acetylsalicylic acid (aspirin) and methyl salicylate (oil of wintergreen)
and characterize them with chemical tests and spectroscopy. These
compounds have been around for a long time but they are still very important
and widely used. The two compounds we are making require just one
reaction each. They both start with the same compound: salicylic
acid. If we react it with the chemical acetic anhydride, we get aspirin,
but if we react it with methanol we get methyl salicylate.
Below you will find a set of questions which you can use to do some
preliminary web-researching on these substances. At the end of the
questions is a set of links to potentially useful sites. The links
are generally to the homepage for the site so you can do your own searching
when you get there. Besides giving you more autonomy over your methods,
this means that the sites may be more useful if you wish to study different
topics than the ones we are interested in here, e.g. for some school project
or for your own personal interest. Of course its perfectly fine if
you use print sources to find the answers. Don't underestimate the
value of your own textbooks, encylopedias or dictionaries or the resources
of a library.
Web Research Questions
1. What is a natural source (an herb or plant) for aspirin? Does the natural source give you aspirin directly or a precursor to it?
2. When and by who was aspirin first synthesized in the laboratory?
3. Methyl salicylate is found naturally in two plants. What are they?
4. Find the molecular formulas and structures for aspirin and methyl salicylate.
5. Are there health risks for teenagers if they take aspirin? If you find any, what are they?
6. Find three medical uses for aspirin besides relief of pain and fever.
7. What is the toxicity of aspirin? Give a typical overdose amount and also the LD50 (specify the animal) for aspirin. What does LD50 mean?
8. Answer question 7 for methyl salicylate.
9. List two common OTC (over-the-counter) products that contain methyl salicylate. What conditions are they used to treat?
10. What is the piezoelectric effect? See if you can find a reference to such an effect occurring when wintergreen candy is chewed.
11. Suppose you were allergic to aspirin. Would eating wintergreen-flavored candy be hazardous?
12. We will make aspirin from salicylic acid with acetic anhydride and we will make oil of wintergreen from salicylic acid with methanol. Are there hazards or toxicities associated with working with our starting materials? Check their MSDS's.
Email me at koster.sand@uwlax.edu
Last Modified 1/11/01