The Wittig reaction is one of the most useful reactions in organic chemistry. Despite its prominence early in the organic chemistry curriculum, the exact mechanism of this reaction is still under debate, and this controversy is often neglected in the classroom. Introducing a simple computational study of the Wittig reaction illustrates the mechanistic uncertainty in this reaction and also demonstrates the use of computational methods in chemistry. This exercise is designed to be used with the Hyperchem software package, but can easily be adapted to other applications, both commercial and freeware. Learning outcomes focus on specific details of the Wittig reaction, the uncertainty of reaction mechanisms in general, and thermodynamic aspects of reactions.

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Utilization of various phosphonates as source for phosphorus by the glyphosate degrading strain Pseudomonas spec. GS was investigated. Metabolites of phosphonate degradation were characterized indicating the cleavage of the C-P-bound as primary step of breakdown. The phosphonate N-(phosphonomethyl)-4'-nitroazobenzene-4-amine (azophon) was characterized as a suitable substrate for detection of C-P-bond splitting activity in vivo. Pseudomonas cells permeabilized by toluene treatment were also capable of phosphonate degradation whereas no in vitro activity of a putative C-P-bond cleaving enzyme was detectable after cell disruption.

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