Category Archives: Spring 2013 Organic Chemistry Lab

What’s the Diels? Part I

This year we preformed the Diels Alder reaction between maleic anhydride and furan. There are many Diels Alder reactions to choose from when planning an organic chemistry lab. I chose this one because it has an interesting history. Diels and Alder concluded that the endo product had been formed when they reported the reaction in […]

An Azo Dye Zoo

This year we performed the “Combinatorial Synthesis of an Azo Dye” experiment with new aniline derivatives. The aromatic nucleophiles were the “traditional” phenolic 1-naphthol, 2-naphthol , and salicylic acid. The aniline derivatives were the three nitroaniline positional isomers. The dye colors were the usual assortment of earthy reds, oranges, and yellows that we have been […]

King Fischer

This year we performed the Fischer esterification synthesis of a series of ethyl cycloalkane carboxylates. The starting carboxylic acids were cyclopropane, cyclobutane, cyclopentane, and cyclohexane carboxylic acid. A couple of the carboxylic acids had a distinctive butyric acid type odor: ugh! We used sulfuric acid an excess of ethanol to complete the reaction. The products […]

Cram Rules in the Kingdom of Grignard Reactions

This Spring we revisited an experiment we had done a couple of years ago that involved adding a phenylmagnesiumbromide Grignard reagent to a series methylcyclohexanone positional isomers. This time I performed an NMR analysis that I had not done before. A 1971 Journal of Organic Chemistry article entitled “Sterochemical Considerations of the Reactions of Phenylmagnesium […]