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Cholesterol - Assignment Example

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During the bromination of the cholesterol, bromine atoms are added to cholesterol to get rid of the double bond by forming…
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Download file to see previous pages Cholesterol bromination can be used to purify cholesterol (Barton, Miller & Young 98).
In most cases, oxidation refers to the addition of the oxygen atom to a substance. However, in organic chemistry, oxidation refers to the loss of bond by carbon atom to hydrogen forming new bonds with other atoms. The overall reaction is characterized by loss of electron density hence loss of the electron. Cholesterol is capable of undergoing both autoxidation and photo-oxidation to produce oxysterols in each case. The common oxidants used for cholesterol oxidation are zinc and sodium dichromate. The first step involves the formation of the ketone, where the O double bond replaces the OH functional group. Then zinc is used to remove the bromine atoms (Stewart, Lee & Can 439).
Debromination is the opposite of the bromination because it involves the removal of the bromine atoms from the organic molecule. It is one of the dehydrogenation reactions where cholesterol dibromide is boiled in the presence of alcoholic halide to produce the corresponding alkene molecule. The chemistry behind this reaction is that the bromine attached to the carbon in the alkyl bromide undergoes a reaction with hydrogen that is attached to the β-carbon that releases the hydrogen bromide. The product of the reaction is the formation of a double bond between α and β carbon resulting into an alkene (House & Row 182).
Isomerization is a process involving the transformation of a molecule into another with the same atoms but different arrangement. The new molecule is called an isomer. In the case of cholesterol, oxalic acid assists in shifting 5-Cholesten-3-one to a 4-Cholesten-3-one by shuffling of the position of the carbon-carbon double bonds. Oxalic acid provides the acidic medium that favors shifting and formation of a double bond to a new location leading to the formation of the conjugated system with the ketone group (Seager, Spencer & Slabaugh 123).
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