Kinetic Production of Isoborneol through the Oxidation-reduction Sequences of Borneol
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Through an oxidation-reduction reaction sequence, Borneol is converted to isoborneol. First, borneol is oxidized through a reaction with sodium hypochlorite at 400C to form camphor. When the camphor is then reduced by sodium borohydride, isoborneol is formed. The percent yeild of isoborneol collected was 56.4%, and the melting point range was found to be between 174.2-179.90C. Through analysis of the product through 1H NMR spectroscopy the percent purity is found to be 77.2% pure isoborneol.
Oxidation-reduction reactions can be used to stereochemically control and produce many different organic molecules. The oxidation step in this process increases the number of carbon oxygen bonds by losing a hydrogen and breaking…show more content…
The sodium hypochlorite was formed by using hypochlorous acid and adding glacial acetic acid and acetone to the solution. These reagents were later removed from the product by washing and transfer of solutions. The unwanted organic layer was removed with dichloromethane. A sodium bisulfate solution removed sodium hypochlorite and acetic acid was removed using sodium bicarbonate. Any water was lastly removed by saturated sodium chloride.
After isolating my camphor product I determined I obtained a 51% yield. I attribute this lower than expected yield to the multiple washing and transferring of products. Using a portion of my product I tested the melting point and had a range of 167.8-173.9oC. I used another sample of the camphor I isolated for 1H NMR analysis. This analysis enabled for assessing the purity of the camphor by looking for a disappearance of the characteristic signal around 4.0ppm of borneol. The camphor sample contained a very small signal at 4.0ppm and not the large doublet expected in a pure sample of borneol. The only other signal found both in the camphor and the borneol was at 7.25ppm which indicates the CHCl3 present in the NMR sample tubes.
As always following oxidation comes the reduction of the camphor to isoborneol. This step, taking place in a methanol solution, was completed by using sodium borohydride which was used as the ion donor. This reduction step