The teaching of organic chemistry is hampered by the lack of pictorial evidence of the reactions that form the bulk of the core organic chemistry curriculum. The reason for this is that most reactions involve neither phase change nor color change, making them of no value as a source of pictorial evidence.  Furthermore, photographing scientific glassware is very challenging because of glare. In this poster we provide visual evidence for the regiochemistry of the oxymercuration of 1-hexyne. The product of the reaction was distilled onto solutions of bromine in CH2Cl2, which was not decolorized, 2,4-dinitrophenylhydrazone, which formed a precipitate, and chromic acid, which was unchanged. The CH3C=O unit was confirmed by a positive iodoform test. The boiling point coupled with the functional group test confirmed the product was 2-hexanone. The reaction of 1-hexyne with bromine is included for comparison with the product.

Development of an aesthetically appealing example of oxymercuration of alkynes

244th National Meeting (2012)

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