Fluorenene to Fluoronone

Topics: Chromatography, Thin layer chromatography, Oxide Pages: 4 (1495 words) Published: May 2, 2012
¬¬The goal of the first part of this experiment was to achieve a 50-50 conversion of fluorene to Fluorenone. In order to achieve the goal of the experiment fluorene was oxidized to Fluorenone. The hydroxide ions from the sodium hydroxide in the presence of Stark’s catalyst would be able to de-protonate the acidic fluorene protons. This would result in the formation of a carbanion which attacks the oxygen from the air resulting in the formation of a hydroperoxide and eventually a ketone (after removal of water). Since the goal was to have a mixture of 50% fluorene conversion, Thin Layer Chromatography (TLC) was carried out several times to assess the rate of the reaction. In order to separate the aqueous composites from the solution extraction was carried out where the product was washed several times with Toluene and HCl and NaCl. In order to dry the excess water and obtain a ketone calcium chloride was used as a drying agent. The data obtained from TLC showed that the Rf value for the starting material was on a range of 0.68-0.75. The Product obtained had varied concentrations of the fluorene and Fluorenone. The average Rf value obtained for the product was 0.205. Through this data, it can be concluded that the ketone (Fluorenone) was more polar that fluorene. This data is theoretically correct as well since ketons are supposed to be more polar than alkenes due to the presence of C=O bond. However, TLC data showed that the conversion of fluorene was not achieved to a 50-50 level but had proceeded even further, almost to a point where none of the fluorene remained in the solution. This was determined because in the last TLC slide the presence of Fluorenone was little (the dots size was smaller than it should have been). This error served as a basis for more errors in the second part of the experiment. Reason for this error was that the TLC was not carried out sooner than it should have been due to which the rate of reaction was inaccurately...
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