Bromination and Debromination: Purification of Cholesterol

Smit Patel
October 21, 2009
Aim: - To purify the cholesterol using the process of bromination and debromination.

Experimental Procedure: - A literature procedure1 was followed for the purification of

cholesterol lab.

Table I Apparatus Cholesterol Dibromide Purified

Cholesterol
Zinc Dust H3C
Ether CH3
CH3
Acetic acid
CH3
3 Erlenmeyer flask CH3
Pipette
Stirring rod
1.005 g Cholesterol
Methanol HO
Calcium chloride
Separatory funnel
10% sodium hydroxide
H3C
CH3
CH3
CH3
CH3

HO
Br
Br

Data
Table II Experimental Value Table III Theoretical Value
Dibromide Cholesterol 1.424g 1.2096g
Cholesterol 141 °C
Temperature
Recrystallize .612g
Cholesterol
Dibromide Cholesterol
Cholesterol 149 °C
Temperature
Recrystallize .600 g
Cholesterol

Result
Sample Calculation % Recovery: - [abs (Theoretical Value – Experimental value)/Theoretical
value)*100
Dibromide Cholesterol % recovery = 15.06%
Cholesterol Temperature % recovery = 5.37%
Recrystallize Cholesterol % recovery =2.0%

Discussion: -the purpose was to recrystallize the cholesterol and find the melting point. Initial
measurement was of cholesterol was 1 gram. Then the cholesterol and bromine was added to
make dibromide cholesterol. When bromine was added to the cholesterol, the compound turns to
yellow color and paste of dibromide promptly result. Sodium acetate was used as anhydrous of
solution. Acetic acid was used to make the crystallize product clear by removing the yellow
color. Acetic acid was used because dibromide cholesterol moist with the acetic acid.
Experimental value of dibromide cholesterol was 1.2096 grams and the theoretical value for
dibromide cholesterol was 1.424 grams. The percent error was 15.06% which is much higher
than expected. The percent error was high because the product was wet this could be one of the
reason. If we let the product there could be less error in our experiment. The other reason some
product might have filtered out from the filtration paper. Third reason possible some product
have been left on the filter paper. So this could be the reason for having percent error for
dibromide cholesterol. The second part of the lab is to recrystallize dibromide cholesterol to pure
cholesterol. In this lab zinc dust, sodium hydroxide, and calcium chloride was used. Zinc dust
become white precipitate in the solution. Sodium acetate was used to remove excess hydrogen
halide from the compound. Calcium chloride was used as anhydrous in solution. The final
product of the recrystallization of cholesterol was .612 gram. The theoretical value was .600
gram. The percent error of the recrystallize cholesterol was only 2% which is very small. The
value could have been improved by recrystallize the product one more time. The error could be
because of the impurities did not filter through the filter paper. There could be some kind of
impurity involved in the product which could not be recrystallized. The product might not be dry
enough to measure it this could be possibly one reason. The final step to find out, how pure the
compound is through the melting point. The experimental melting point was 141 °C and the
theoretical melting point was 149°C. The error came out to be 5.37%. Since the compound was
not pure so the error in the melting point was expected but the error came out to little higher than
expected. The error is higher because the melting point apparatus was not calibrated so melting
point value could be higher or lower. That could maximize or minimize the error in the
experiment. But in spite of that there was still impurity present in the compound it could be
because of filter paper. There might be something on filter paper before it has been used. There
were a lot of places the experiment could have been done it better.

Conclusion
The percent recovery for dibromide cholesterol, cholesterol temperature, and recrystallize
cholesterol was 15.06%, 5.37%, 2.0% respectively.
Reference
1. Williamson, K, Minard, R, & Masters , K, (2007). Macroscale And Microscale Organic
Experiments. New York, NY: Houghton Mifflin.