IGEM:Maryville University-St. Louis/2009/Notebook/Organic Chemistry Notebook

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This project involves experiments done at Maryville University for CHEM 203-4. 
1 Measurement of Physical Properties 
2 The Separation of a 1 L Mixture of Heptanol (bp 153 oC) and Cyclohexanol (bp 160 oC) 
by Gas Chromatography 
3A Simple Distillation at the Semi-Microscale Level: Separation of Ethyl Acetate from trans-  1,2-Dibenzoylethylene
4A Determination of a Partition Coefficient for the System Benzoic Acid, 
Methylene Chloride and Water 
5A Reduction of Cyclohexanone to Cyclohexanol Using a Metal Hydride Reagent 
6A Purification of trans-1,2-Dibenzoylethylene
7 The Cannizzaro Reaction with 4-Chlorobenzaldehyde: 4-Chlorobenzoic Acid and 
4-Chlorobenzyl Alcohol (two lab periods)
8A The Esterification Reaction: Ethyl Laurate
11A Isolation of an Optically Active Natural Product: Usnic Acid
11B Demonstration of the Purification of Caffeine by Sublimation
The second semester includes: Diels-Alder Reaction 14, The Perkin Reaction 18, 
Aldol Reaction 20, Williamson Synthesis of Ethers 22B, Synthesis of Cyclic 
Carboxylic Anhydrides: Succinic Anhydride 25A, Phthalic Anhydride 25B, 
Halogenation: Electrophilic Aromatic Substitution to Yield 4-Bromoacetanilide 28, 
Nitration: 2,5-Dichloronitrobenzene 29A, Nucleophilic Aromatic Substitution: 
2,4-Dinitrophenylthiocyanate 30, Hypochlorite Oxidation of Methyl Ketones by 
the Haloform Reaction: Benzoic Acid 34A.


  • Students meet in room K-2117 at Maryville University for the laboratory.
  • The first semester is in the fall and the second semester is in the spring.
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