what is the order of elution of fluorene and fluorenone from the column and tlc

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Purpose: Oxidize fluorene to fluorenone, separate the products by column chromatography, and determine a percent conversion of reactant to product.. Preparation: Read Mayo, et al., p. 139-142. Look up and record the melting points, molar masses, and structures of fluorene and fluorenone. Writing a balanced equation for this oxidation-reduction reaction is complex. The oxidation of fluorene [symbolized by (C12H8)>CH2] to fluorenone [symbolized by (C12H8)>C=O] involves a 4 electron transfer: (C12H8)>CH2 + H2O ------> (C12H8)>C=O + 4H+ + 4e- while the oxidizing agent, dichromate, undergoes a 6 electron reduction: Cr2O7-2 + 14H+ + 6e- ------> 2Cr+3 + 7H2O Now it is necessary to join these two half reactions into a single reaction in which the electrons lost cancel with the electrons gained. Some cancellation will also occur with H+ and H2O. Using the above information write a complete equation for the reaction in your results section.. Using the procedure below, only part of the fluorene is oxidized and fluorenone is not formed quantitatively. Column chromatography is used to separate the product, fluorenone, from the remaining fluorene. Note that dichromate is a versatile oxidizer but it is also poisonous and all chromium compounds need to be disposed of separately

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