Friday, October 06, 2006

Enols

Today we started to look at enols, with the major focus being a mechanistic view of the keto-enol tautomerism process. We saw how aqueous acid and aqueous base can catalyze the tautomerism. The key here is the realization that water can be an acid, a base, or a nucleophile -- it all depends on the conditions.

Once we saw how enols can be formed, we spent some time on reactions that they can undergo. The template here was the use of the C=C as a nucleophile from Chem 241. Our example was dibromine as the electrophile, we then took it a step further and looked at the venerable Hell-Volhard-Zelinsky reaction, in which a carboxylic acid is converted to an alpha-bromo acid.

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