Abstract: This lab converted borneol to camphor using a green oxidation. Sodium hypochlorite was used instead of the less “green” Jones reagent. Borneol was mixed with glacial acetic acid and oxidized with sodium hypochlorite to make crude camphor. The crude camphor was purified by sublimation. The final product was characterized by obtaining a melting point and inferred spectroscopy. The experiment was carried out to see if bleach could oxidize borneol and if it is greener than using a Jones reagent. Sure enough camphor was made with a 4.03 g of unsublimed camphor and 0.08g of pure camphor with a 2 % yield (in moles). No melting point or IR peaks were obtained. However, the literature value of the melting point is 177.0 °C and an IR peak from 1680-1750 cm-1 with no alcohol peak.
Introduction:
Oxidations are used in organic chemistry to perform certain tasks in a laboratory. Visualizing how an oxidation reaction works in organic chemistry is a bit more difficult to point out than in general chemistry. But the concept is still the same. The idea of an oxidation reaction is to decrease the electron density around a carbon. Essentially, it is the loss of an electron around a carbon. To identify if an oxidation has occurred in organic chemistry the following could happen: replace a less electronegative atom with a more electronegative atom; replace a bond to hydrogen with a bond to oxygen; or replacing a single bond with a double bond by the loss of hydrogen. Oxidations are very convenient when trying to synthesize an aldehyde or ketone for this reason.
Since there is less electron density around a reactive carbon center, the oxidation n of the carbon will be more positive. Usually a more electronegative atom such as a halogen, nitrogen, or oxygen replaces hydrogen bonded to the carbon. The oxidation states of these atoms are -1(and =O is -2) and +1 for hydrogen. So to balance these negative atoms the carbon must change