Isoborneol Reduction

The goal of this experiment was to reduce Camphor into Borneol and Isoborneol using Sodium Borohydride. In this reaction, Isoborneol was the major product while Borneol was the minor product. This is a reduction reaction, where the ketone on the Camphor is reduced to form two products with secondary alcohols. First, 0.25 grams of Camphor was obtained and added to a 50ml flask and mixed with 1.5 ml of methanol. Second, 0.25 grams of Sodium Borohydride was added to the reaction mixture and the reaction mixture was boiled for 2 minutes. Third, the mixture was left to cool and 10ml of water was added to it. The reaction mixture was then filtered using a Buchnels funnel and the filtered product was placed in a 50 ml Erlenmyer flask. Fourth, …show more content…
Gas chromatography was done on the final product (the gas chromatography results were from another student) and the two peaks appeared. The area under one peak appeared to be 85.63216% while the area under the other peak appeared to be 14.36783%. The 85.63216% area under one peak represents Isoborneol, while 14.36783% area under the other peak represents Borneol. It is logical that the major product Isoborneol is present in larger quantity in the product mixture compared to Borneol, since in the reduction mechanism Isoborneol production is far more likely to happen. Also an NMR was done on the final product and based on this, the relative amounts of the two products and their identities were confirmed. Isoborneol was 80.3% of the final product, while 19.7% of the product was Borneol. This was concluded because Isoborneol should be the major product in the reduction of Camphor. As such, it is likely that more of it was formed during the actual reaction. Likewise, Borneol should be the minor product in the reduction of Camphor. As such, it is likely that less of it was formed during the actual reaction. The experiment began with 0.250 grams of Camphor, and since Camphor is also the limiting reagent, 0.250 grams of the final product should be obtained. In the experiment, 0.212 grams of the product was obtained leading to a percent yield of 84.8%. Some reasons why the percent yield was not 100 percent could include some of the Camphor falling off the weighing paper while it was transferred from the weight scale to the 50ml flask. Also, not all of the filtered product might have been removed from the Buchnel’s funnel thus leading to a low percentage