Thomas Wallace

Logan Hoggard 2315-008

Baker's Yeast Reduction of an Alpha-Diketone

Introduction The purpose of this experiment was to turn 1-phenyl-1,2-propanedion into 1-phenyl-(1R,2S)1,2-propanediol. To do this while attaining correct stereochemistry, baker's yeast was used for the reaction. However, this experiment was largely a failure due to the inability to obtain any product. One of the main reasons for this may have been the very short time the reaction was allowed to proceed. Most reactions of this kind may be left for several days, while this was only left to react for about an hour.

Results/Discussion The result of this experiment was largely a failure as none of the product was ever isolated. This may have been due to a number of factors. When running the solution through the micro column, no distinct band was observed. This could have been due to the product being lost by this point. After the column, the solution was placed in the rotovac and it was entirely removed. This could have been because there was actual no product left by this point, or because the mixture was heated too heavily and both the product and the solvent were pulled off. However, it seems most likely that the lack of product was due to the very short reaction time. The enzymatic reaction is a relatively slow one and only allowing it to proceed for an hour may have left such a small amount of product that it was then lost in the column. Due to the lack of any product whatsoever, the optical rotation test was impossible to perform. If this experiment was to be repeated, it would be better to allow the yeast mixture more

time to react. This would likely yield a much greater amount of product. Another improvement would be using a larger column to obtain a better separation of the compound. As no final product was collected, it is difficult to tell where the biggest mistake was made. The best guess that can be made is that there was only a very small amount of product formed due to the short time the yeast mixture was allowed to react.

Conclusion In conclusion, this was a very unsatisfactory experiment that yielded no conclusive result, and also gave very little indication as to the source of error. However, it seem most likely that the biggest factor was the timescale on which this experiment was run, the attempt to take a reaction that can often run for several days and condense it into several hours. If this experiment where to be repeated, the first thing to try would be a longer reaction time.