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Bromination And Debromination Of Cholesterol Biology

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    Bromination/debromination which is an of import organic reaction that aims in purification of petroleum cholesterin from drosss which include 3-cholestanol, 7-cholesten-3-ol, and 5,7-chlestadien-3-ol was performed in a research lab graduated table for two hebdomads. Due to steric restraints, merely cholesterin reacted with Br and crystallized from the solution doing it possible to be separated ( Feiser, and Williamson 63 ) . The dibromocholesterol formed is regenerated by responding with Zinc dust. In add-on, three methods were used to measure the effectivity. These were Sodium Iodide trial, Silver Nitrate trial, and Sulfuric acid trial. NaI trial showed a positive response as colour changed to yellow. The formation of the precipitate besides indicated a positive consequence. The Na iodide reagent reacted with 1A° and 2A° alkyl halides through an SN2 mechanism.A On the other manus, the Ag nitrate reagent reacted with 2o and 3A° alkyl halides through an SN1 mechanism.A Negative consequences were observed for both the commercial cholesterin and 1-chlorobutane ( Zubrick 38 ) . Conversely, the t-butyl chloride gave a positive consequence for the AgNO3A trial and a negative consequence for the NaI trial. The synthesized cholesterin was 0.29 gm and the theoretical output was 1.08 gm. This gave a percent output of 26.9 gm. Although this was a low output the TLC analysis confirmed a high pureness of the synthesized cholesterin. The runing point of the synthesized cholesterin and commercial cholesterin seems to fall in the same scope. This confirms the pureness of the synthesized cholesterin. TLC analysis was carried out to corroborate the pureness of the analysis. The distance traveled by commercial cholesterin was 5.5 whereas that travelled by the synthesized cholesterin was 4.6. The absence of other musca volitanss on the TLC home base confirms that there were no taints present in the sample.

    Introduction Cholesterol is an of import steroidal compound found in both animate beings and workss. Despite the fact that cholesterin causes diseases, it plays a critical function in life. For illustration, cholesterin is the chief structural constituent in cell walls and in myelin sheath formation. It is besides a major precursor for most steroid endocrines. Crude cholesterin is isolated from natural beginnings and assorted methods have been used in its purification. Crude cholesterin contains about 3-5 % taint. Some of the contaminations are 3-cholestanol, 7-cholesten-3-ol, and 5,7-chlestadien-3-ol shown below.

    Figure 2: Some common contaminations of commercial cholesterin The chief aim of this experiment was to sublimate commercial cholesterin utilizing organic reaction chemical science, including the usage of the electrophilic add-on. For complete purification of cholesterin from the above drosss is achieved by a reaction of Br with cholesterin to bring forth dibromocholesterol. Because of the steroid ring construction nowadays in these compounds that causes steric restraints, merely cholesterin reacts with Br to organize an indissoluble diaxial dibromo compound through electrophilic add-on. On the other manus, cholestanal does non respond with Br and the other two contaminations are dehydrogenated by Br taking to formation of soluble dienes and trienes severally. The dibromo-cholesterol precipitates as a solid go forthing the other drosss in the reaction dissolver. A purification measure such as solvent lavation or crystallisation is carried out to divide the solid from the drosss. The solid dibromo-cholesterol is so reacted with Zn in order to renew pure cholesterin.

    Figure 1: Chemical reaction Scheme for the Bromination/Debromination of Cholesterol To prove the effectivity of this reaction three different chemical trials viz. sodium iodide in propanone, Ag nitrate in ethanol trial, and sulphuric acid trial, were performed. Each of these trials is selective for a specific functional group. Dibromocholesterol contains both primary and secondary alkyl halides and reacts with a Na iodide in propanone and Ag nitrate in ethyl alcohol to organize a precipitate or a nebulose solution. In add-on, the presence of dual bonds in dibromocholesterol in signifier of olefine makes it possible for the formation of a fluorescent green sulphuric acid bed and a ruddy trichloromethane bed when reacted with sulphuric acid ( Landgrebe 78 ) .

    Material and Methods 1g of commercial cholesterin was added to a 25 milliliter Erlenmeyer flask. 7 mL t-butylmethyl quintessence was measured with a calibrated cylinder and added to the flask incorporating the cholesterin and a magnetic splash saloon. A H2O bath was so set up on the hot plate in the goon. The Erlenmeyer flask contain the reaction solution was inserted into the H2O bath and clamped as shown below. The heat and the scaremonger were turned on and gently heat until all the cholesterin dissolved in t-butylmethyl quintessence.

    Figure 3: A Set-up for bromination reaction ( Note: the existent reaction mixture is non bluish )

    The flask was removed from the H2O bath after all the cholesterin was wholly dissolved and allowed to chill to room temperature. After the cholesterin solution was cooled, the flask was clamped to the ring on the hot home base as shown in figure 4 and stirred without heating. A burette was so used to distribute 5 milliliter of bromine solution into the flask. A hasty solution formed about instantly.

    Figure 4: A Set-up for the Addition of Bromine

    The H2O bath was replaced with ice and tap H2O and the reaction solution stirred intermittently with a glass splash rod for ~ 10 proceedingss to finish the crystallisation of the merchandise. About 20 milliliter of the t-butylmethyl quintessence – acetic acerb solution was so dispensed in a clean 50 milliliter Erlenmeyer flask which was clamped to a ring base and allowed to chill in the ice bath. A vacuity filtration was done utilizing a Buchner funnel and filter paper. The solid in the filter was washed utilizing ~10 milliliter of the cooled solution of t-butylmethyl ether – acetic acid and so with ~10 milliliter of methyl alcohol. The solid was so allowed to dry with the vacuity on for about 5 proceedingss. the dibromocholesterol runing point was measured and recorded. The dry solid was weighted and sealed in a vial and stored for following experiment. To debrominate cholesterin, 20 milliliter of t-butylmethyl quintessence, 5 milliliter of acetic acid and 0.2 g of Zn dust were added into the Erlenmeyer flask incorporating the dibromocholesterol solid. The mixture was swirled for 5-10 proceedingss in the goon and sonicated in 5 proceedingss to let the reaction to travel completion. After sonication the solids nowadays were removed by gravitation filtration method into a clean 125 milliliter Erlenmeyer flask. The filtrate was transferred to a 125 milliliter separatory funnel in which 20 milliliter of deionized H2O was added, shaken and allowed to divide into beds. The two beds formed were so separated as H2O beds and organic ( ether ) beds. The quintessence bed was washed with 20 milliliters of 10 % NaOH and so 20 milliliter of concentrated NaCl solution. 100mg of the drying agent Mg sulphate was added to the organic bed and the solution swirled until dry. The drying agent was removed by gravitation filtration utilizing a glass funnel fluted filter paper and a really dry 50 milliliter Erlenmeyer flask. The flask was placed in a warm H2O bath and so ice cooled for 10 proceedingss until all but 5 milliliter of the quintessence remained following a hasty formation from the solution. The staying dissolver was decanted and the synthesized cholesterin transferred and allowed to dry in the goon for 20 minutes.The dry solid was weighed and the weight recorded. In add-on the thaw point was besides taken and recorded. To measure the effectivity of the bromination reaction three chemical reactions mentioned above were carried out. NaI in acetone trial Five trial tubing labeled A, B, C, D and E were used for this test.A About 30 milligram of the commercial cholesterin get downing stuff was added to tube A ; ~30 milligram of dibromocholesterol to tube B ; ~30 milligram of the synthesized cholesterin merchandise to tube C ; ~0.3 milliliter of 1-chlorobutane to tube D ; and ~ 0.3 milliliter of t-butyl chloride to tube E.A In add-on, approximately 3 milliliters of propanone was added to each tubing to wholly fade out all the compounds.A Solutions A-E was used to make the NaI in acetone trial every bit good as the AgNO3 in ethanol trial. Tubes A-C did the TLC every bit good. The NaI in Acetone and AgNO3 in Ethanol trials were performed by puting up a trial tubing rack incorporating ten little trial tubing. The trial tubings were labeled N1 – N5 and A1 – A5. 1 milliliter of NaI in propanone reagent was added to prove tubings N1 – N5, and 1 milliliter of AgNO3 in ethanol reagent to prove tubings A1 – A5. This was followed by adding 5-8 beads of A solution to prove tubing N1 and tubing A1, 5-8 beads of solution B to prove tubing N2 and tubing A2, 5-8 beads of solution C to to prove tubing N3 and tubing A3, 5-8 beads of solution C to prove tubing N4 and tubing A4, and 5-8 beads of solution C to prove tubing N5 and tubing A5. The trial tubings were heated for a piece and all the observations recorded. The sulphuric acid for olefines trial was performed by extra solutions of cholesterin and dibromocholesterol with five dry-cleaned trial tubes 1-5. 10 milligram of commercial cholesterin was placed in tubing 1, ~10mg of the dibromocholesterol to tube 2 ~10 milligram of your synthesized cholesterin to tube 3, ~10 milligram of 2-chlorobutane to tube 4, and 10 milligram of cyclohexene to tube 5.A About 1 milliliters of trichloromethane ( CHCl3 ) was added to each tubing and whirl to wholly fade out all solids.A In add-on, 0.5 milliliter of H2SO4 was so added to each tubing. The observation for this reaction was recorded in the notebook. The TLC analysis of cholesterin and dibromocholesterol was performed by obtaining a silicon oxide gel TLC home base and puting it up to run TLC analysis on solutions A-C above. The home base was spotted with each solution and developed by puting the home base utilizing 30 % ethyl ethanoate: 70 % hexane as the nomadic stage. The developed home bases were viewed under UV lamp and in the I2 chamber and observations recorded.

    Consequences Table 1 Percent Yield of synthesized cholesterin

    Actual Output

    0.29g

    Theoretical Output

    1.08g

    Percent Output

    26.9 %

    Mass of Synthesized Dibromocholesterol was 1.57g

    Table 2 Melting Point Test

    Compound

    Temperature A°C

    Commercial Cholesterol

    144.6-150.3

    Dibromochesterol

    105-109

    Synthesized Cholesterol

    147

    Table 3 Sodium Iodide trial

    Compound

    Time

    Vortex

    Temp

    First Sign of Reaction

    Com. Cholesterol

    None

    Dibromocholesterol

    +

    Yellow

    Synthesized Cholesterol

    +

    Chunky & A ; Yellow

    1-Chlorobutane

    +

    Yellow

    Tert-Butyl Chloride

    +

    Cloudy

    Table 4 Silver Nitrate trial

    Compound

    Time

    Vortex

    Temp

    First Sign of Reaction

    Com. Cholesterol

    None

    Dibromocholesterol

    +

    Cloudy

    Synthesized Cholesterol

    +

    Cloudy & A ; Yellow

    1-Chlorobutane

    None

    Tert-Butyl Chloride

    +

    Cloudy

    Table 5: Sulphuric Acid Test

    Compound

    Time

    Vortex

    Temp

    First Sign of Reaction

    Com. Cholesterol

    +

    Color

    Dibromocholesterol

    +

    Color

    Synthesized Cholesterol

    +

    Color

    1-Bromobutane

    None

    Tert-Butyl Chloride

    +

    Color

    Table 6: Thin Layer Chromatography: In 30 % Ethyl Acetate/70 % Hexane

    Commercial Cholesterol

    5.5

    1.0

    5.5

    Dibromocholesterol

    4

    0.73

    5.5

    Synthesized Cholesterol

    4.6

    0.84

    5.5

    Discussion

    The output of the synthesized cholesterin was.29 gms ( Table 1 ) . The theoretical output was 1.08 gms. The existent output was calculated by taking the difference of the weight of the unit of ammunition underside flask and the synthesized cholesterin by the synthesized cholesterin ‘s weight entirely. The per centum output was calculated to be 26.9 per centum. The synthesize procedure was non efficient due to the low output and percent output of the synthesized cholesterin.

    The runing point of the synthesized cholesterin and commercial cholesterin seems to fall in the same scope. This confirms the pureness of the synthesized cholesterin. NaI trial showed a positive response as colour changed to yellow. The formation of the precipitate besides indicated a positive consequence. The Na iodide reagent reacted with 1A° and 2A° alkyl halides through an SN2 mechanism.A On the other manus, the Ag nitrate reagent reacted with 2o and 3A° alkyl halides through an SN1 mechanism.A Negative consequences were observed for both the commercial cholesterin and 1-chlorobutane. Conversely, the t-butyl chloride gave a positive consequence for the AgNO3A trial and a negative consequence for the NaI trial. The stationary stage of the TLC trial was the silicon oxide gel TLC home base and the nomadic stage was 30 % Ethyl Acetate/70 % Hexane ( Table 6 ) . The distance traveled by commercial cholesterin was 5.5, and for the synthesized cholesterin was 4.6. The difference in the distance traveled and the Rf values of the samples commercial and synthesized cholesterin were pure. Since there were no other musca volitanss seeable on the TLC home base was a clear indicant that there were no taints of other chemical compounds present in the sample.

    Bromination And Debromination Of Cholesterol Biology. (2016, Dec 09). Retrieved from https://graduateway.com/bromination-and-debromination-of-cholesterol-biology-essay/

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