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18 March 2008
Flourenone Synthesis and Column Chromatography
Chromatography, simply, is the separation of components from a mixture.
are many different types of chromatography including paper, liquid, gas, thin-layer, and
for the use of this experiment, column chromatography.
Column chromatography is a
type of component separation that can be used in large and small scales as a
In column chromatography, a stationary phase (polar solid, in
this case being Alumina), is placed in a glass column and a mobile phase (less polar
liquid, in this case hexanes), is added to the top and flows down through the column (by
either gravity or flash chromatography).
Flash chromatography, used in this
experiment, is a solvent force by air pressure.
With the polar stationary phase and the
less polar mobile phase, the components of a mixture can be separated according to
It will be seen that the less polar components elute first, leaving the more
polar components contained by the stationary phase longer.
This method is
comparable to TLC chromatography in terms of its mobile and stationary phases and
TLC seems to be more advantageous because of its ability to perform
multiple analyses concurrently and it is an easy and fast way of obtaining results.
this experiment, the column and TLC chromatography will be done on the reaction of
Fluorene to Flourenone.
Fluorene is oxidized under basic conditions and then
deprotonated, forming a hydroperoxide.
This, in turn forms Flourenone.
This can be
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seen by the diagram and electron-pushing mechanism shown below.
The diagram is
the products, reagents and reactants diagram, showing the beginning and end of the
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This note was uploaded on 03/18/2008 for the course CHEM 213 taught by Professor Masters,katherinelorenzo,peterbisch,amberwilcox,jenniferlchen,ying during the Spring '07 term at Pennsylvania State University, University Park.