Synthesis Of Borneol Lab Report

The goal of experiment four was to use sodium dichromate to oxidize borneol to camphor. To purify the camphor use sublimation, then reduce camphor to isomeric alcohol isoborneol with sodium borohydride. Use the 1H NMR to determine the ratio of borneol to isoborneol in the final product. The experiment was carried out by using sodium dichromate to oxidize a borneol solution that was made with borneol and ethyl acetate. Once the reaction was complete the mixture was transferred into a separatory funnel where the ether and aqueous layers were separated and the aqueous layer was then extracted with two portions of ether. All ether layers were combined and extracted once again with 10% sodium bicarbonate and water. Once the ether layer was

On the IR spectrum of camphor, a carbonyl functional group (C=O) appeared at 1737 cm-1 with a very large peak. There was also two C-H stretches on the IR spectrum between 2873-2956 cm-1. The SDBS of the true camphor showed all of these same peaks around the same wavenumber. With this observation the oxidation of borneol to camphor was a success. On The IR spectrum of isoborneol, a carbonyl functional group also appeared around 1735 cm-1 but with a smaller peak of the carbonyl group found in camphor. There was two C-H stretches between 2873-2948 cm-1. The spectrum also showed a relatively large hydroxyl group (OH) between 3367-3448 cm-1. The SBDS of the true isoborneol showed all the same peaks around the same wavenumber besides the carbonyl group. True isoborneol does not contain a carbonyl group. Presence of the carbonyl group in the IR spectrum indicated that the reaction didn’t go to completion but it did somewhat reduce camphor into isoborneol because a hydroxyl group formed. If the reaction didn’t go to completion at all and didn’t successfully reduce camphor to isoborneol then a hydroxyl group would not be present. The impurity to the final product would most likely be borneol, because when sublimed for purity the temperature was not controlled and both isoborneol and borneol sublime for