Experiments

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This course is designed to provide an introduction to the basic techniques and procedures of Organic Chemistry, thus furthering your understanding of the fundamentals of this science. It is assumed that you are acquainted with general techniques employed in the laboratory, such as weighing, measuring volumes, preparing solutions, determining temperatures, etc. You should also be familiar with the basics of Organic Chemistry including nomenclature, structural theory and the reactions of common functional groups. Familiarity with the spectroscopic properties of organic compounds would also be helpful. These experiments are designed to be used in college and university level chemistry laboratory courses, and should not be conducted unless there is an appropriate level of supervision, safety training, personal protective equipment and other safety facilities available for users.

1: Synthesis of Aspirin (Experiment)
Analgesics are compounds used to reduce pain, antipyretics are compounds used to reduce fever. One popular drug that does both is aspirin.
2: Synthesis of Acetaminophen (Experiment)
Analgesics are compounds used to reduce pain, antipyretics are compounds used to reduce fever. One popular drug that does both is aspirin, another is acetaminophen which is often used by people who have unwanted, harmful side effects to aspirin. Acetaminophen, which can be synthesized from p-aminophenol, is probably best recognized under the trade name Tylenol.
3: Extraction of Caffeine (Experiment)
Caffeine is a minor constituent of tea, coffee, and other natural plant materials. The major constituent of tea is cellulose which is not water soluble. Caffeine is water soluble but so are some tannins and gallic acid which is formed in the process of boiling tea leaves. The latter two components can be converted to their calcium salts which are insoluble in water. The caffeine can then be extracted from the water by methylene chloride in almost pure form.
4: Thin Layer Chromatography (Experiment)
You will be using prepared tlc plates which are research quality ($1.50/sheet). Each large TLC sheet will be carefully cut to provide mini tlc plates. Do not touch the adsorbent with your fingers, hold the plates at the sides. Do not use ink on the plates, write in pencil lightly.
5: Synthesis of Isopentyl Acetate (Experiment)
The reaction of a carboxylic acid and an alcohol produces an ester and water. The reaction is catalyzed with acid. Esters often have a fruity taste or odor. Octyl acetate, prepared using octanol as the alcohol, will remind you of oranges. You will prepare a compound which smells like bananas.
6: Steam Distillation of Methyl Salicylate, Hydrolysis of an Ester (Experiment)
You will be steam distilling methyl salicylate.
7: Distillation of a Mixture (Experiment)
In this experiment, you will be conducting both a simple distillation and a fractional distillation of a mixture of cyclohexane (bp=79°) and methylcyclohexane (bp=101°) to compare the two techniques.
8: Identification of Unknowns (Experiment)
9: Multistep Synthesis (Experiment)

Contributors and Attributions

James Chickos, David Garin, and Valerian D'Souza. University of Missouri–St. Louis; Chemistry)

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