Cholesterol Synthesis Lab Report

Cholesterol is a steroid alcohol that is constituted as a nonsaponifiable lipid. All steroids play an important role in the secretion of blood in which is vital for the human body to function properly. The carbon-carbon double bond in cholesterol makes the molecule as a whole immensely more reactive than other alkanes. Cholesterol’s ability to be reactive allows it to be capable of undergoing addition reactions because the pi bond electrons can easily bond to other atoms. The addition of a halogen, in this experiment, bromine, creates a vicinal dibromide. The mechanism behind this addition reaction begins with the bromine-bromine bond breaking due to an attack by the alkene nucleophile. This also ensures that bromine does not end up with more

The solution is pale yellow in color, and from this it is assumed that the bromine is in excess and the cholesterol is the limiting reagent. The cholesterol dibromide solution is placed in an ice bath, the reason behind this is that the colder the environment is, the less soluble the solution becomes, therefore, the cholesterol dibromide begins to crystallize. In this experiment, it took a while for the cholesterol dibromide to fully crystallize, so acetic acid was added as a precipitant. A wash solution is prepared which consisted of acetic acid and methyl tert-butyl ether to rinse the flask for the solid cholesterol dibromide that was stuck to the flask. Cholesterol dibromide was isolated by using the vacuum filtration technique. Before the cholesterol dibromide was vacuum filtered it was a solid sticky white paste. Cholesterol is the limiting reagent, meaning the original amount of cholesterol that the experiment started with, should be equivalent to the number of moles of cholesterol dibromide, if the reaction was completed. In this experiment, the theoretical yield for cholesterol dibromide was 170 mg, but the actual amount recovered was 81 mg, giving a 48% yield. The literature melting point of cholesterol dibromide is 105℃ and the melting range from the recovered