The Wittig Reaction - T he Wittig Reaction Performed on...

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The Wittig Reaction Performed on 6/29/10 Results: 2-nitrobenzaldehyde (.077g ) was reacted with methyl (triphenylphosphoranylidene) acetate (.174g ) in .100g silica gel to form the alkene product referred to in Table 1 of the prelab. This was accomplished via a solid phase Wittig reaction initiated by microwave radiation. After purification using silica gel phase column chromatography, it was determined though TLC analysis that that vials 1, 2, and 3 contained the desired product. The Rf values for these vials were .56mm, .56mm, and .57mm, and these spots correlated to absence of starting material (Rf = 0.11mm). The weight of the purified alkene product was .050g (47.2% yield), and had a melting point of 54.2-61.4°C. Discussion: The reaction was fairly successful with a higher than expected percent yield with the loss of product seen in the two test tubes that contained both products and were thus unusable. To determine the major alkene isomers in this reaction, both the arrow pushing diagram (see Figure 1 below) and the NMR spectra were taken into consideration. In the diagram you can see that the NO2 group sterically hinders the
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This note was uploaded on 10/08/2010 for the course CHEM 3BL taught by Professor Chunmei during the Spring '08 term at University of California, Berkeley.

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The Wittig Reaction - T he Wittig Reaction Performed on...

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