Orgo Lab report Green Oxidation of Borneol

Orgo Lab report Green Oxidation of Borneol - Green...

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Green Oxidation of Borneol By Joanne Hong Lab Instructor: Ian Childers November 11, 2011 Purpose
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The purpose of this lab is to use green oxidation conditions in which Oxone® is combined with a catalytic amount of sodium chloride in order to oxidize the natural terpene, (1S)-borneol, to (1S)- camphor. The isolated camphor product will then be dried, sublimed and assessed by melting point and IR spectroscopy. Compounds (1 S )-borneol (1 S )-camphor Mechanism Procedure (1 S )-borneol was dissolved in ethyl acetate, and then combined with oxone, sodium and water. The solution was stirred for 50 minutes before sodium chloride was added. Solid sodium bisulfide was added to the solution to reduce any remaining oxidants. Once it was determined that there were no remaining oxidants in the solution, the contents were transferred to a separatory funnel. The aqueous layer was extracted three times using ethyl acetate. The organic phases were combined, washed with brine, dried over magnesium sulfate, and then heated to remove the ethyl acetate. The product was placed in a desiccator (Ziploc bag with solid CaCl2) to be further dried. After two weeks, the crude product was sublimed in a covered Petri dish on a
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Orgo Lab report Green Oxidation of Borneol - Green...

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