Bettina De Mesa

Ochem 221L Fall 2014

December 5th 2014
Bromination and Debromination
Data:
Substance
Cholesterol

Grams
Used
1.0230
g

Grams
Recovered
0.6812g

Percent
Yield
31.88%

Color

MP

White

145C- 147C

Calculations:
Sample Calculation % Recovery: - (Theoretical Value Experimental
value)/Theoretical value)] X 100
[(1.0g-0.6812g)/(1.0g)] *100 = 31.88%
Discussion:
The purpose of this experiment is to re-crystallize and purify commercial
cholesterol and to find the melting point of the resulting product. The reagent used
in the process was tert-butylmethylether (MTBE), due to the fact that the ether
doesnt dissolve the cholesterol bromide or its impurities. By adding acetic acetic
acid and bromine together to start the bromination process, the product of
dibromide crystallizes in as quickly as two minutes. The alkene of the cholesterol
nucleophilically attacked the bromine and then formed a tertiary carbocation.
Subsequently, the bromide ion made a backside attack to create dibromide. In order
to complete the crystallization process, the orange-ish solution was placed in an ice
bath followed by vacuum filtration through the Hirsch funnel. The loss of product
can be attributed to its presence in the mother liquor. Once finished, the process of
zinc dust debromination occurs in order to return to a non-halogenated product. The
crystallized dibromide was then dissolved in a reagent mixture of acetic acid,
MTBE , and the zinc dust to ultimately form re-crystallized cholesterol at the end of
the experiment.
When the crystallized dibromide was mixed with the solution, the zinc acetate
began to precipitate resulting in a cloudy white solution. The solution was then
added to a seperatory funnel, removing the zinc dust and some product of
cholesterol. Four different washes occurred, twice with water to remove the zinc
acetate, once with sodium hydroxide to remove the acetic acid and once with
saturated sodium chloride to reduce the water content. The ether solution was

collected, dried and evaporated by a hot water bath to crystallize a final product of
0.6812g of cholesterol. The melting point was then assessed to yield a range of
145C -147C.