free-radical chlorination
Chem 310-003
February 9th, 2013
Conclusion: Free Radical Chlorination
The primary purpose of this experiment was to carry out the chlorination of 1-chlorobutane so that dichlorobutane formation was favored. Gas Chromatography was used to analyze the amount of dichlorobutane isomer produced in the free radical reaction. A mixture of 8mg of catalyst, 1mL of 1-chlorobutane, and 0.32mL of sulfuryl chloride was added to a microscale reflux apparatus. After 17mins the reaction was complete, and 1mL of deionized water was added to the collected solution. The aqueous layer (bottom layer) was removed. Next, 1mL of 5% sodium bicarbonate was added and once again the aqueous layer (bottom layer) was removed. Finally, 1mL of water was added and the organic layer (top layer)was removed. The organic layer was dried with anhydrous sodium sulfate, and then added to a vial for Gas Chromatography testing. Before conducting the experiment a prediction was made as to which free radical intermediate would be most stable and which isomer would yield the most product formation. Based on the results, it can be concluded that 1,3-dichlorobutane was both the most stable and produced the most product. This free radical intermediate was followed by 1,2-dichlorobutane, 1,4-dichlorobutane, and lastly 1,1-dichlorobutane. Based on the results 1,3-dichlorobutane produced 37% product, more than three times as much product as the least stable free radical intermediate 1,1-dichlorobutane produced. The isomer of 1,3-dichlorobutane produced the greatest yield and can be determined as the most stable free radical form of 1-chlorobutane because of the location of its free electron. The lone electron is located on a carbon with many alkyl groups surrounding it. The more groups attached to the carbon with the lone electron, the more stable of a form it is. This is a pattern seen throughout the stability rankings for the four free radical possibilities, for example when the
February 9th, 2013
Conclusion: Free Radical Chlorination
The primary purpose of this experiment was to carry out the chlorination of 1-chlorobutane so that dichlorobutane formation was favored. Gas Chromatography was used to analyze the amount of dichlorobutane isomer produced in the free radical reaction. A mixture of 8mg of catalyst, 1mL of 1-chlorobutane, and 0.32mL of sulfuryl chloride was added to a microscale reflux apparatus. After 17mins the reaction was complete, and 1mL of deionized water was added to the collected solution. The aqueous layer (bottom layer) was removed. Next, 1mL of 5% sodium bicarbonate was added and once again the aqueous layer (bottom layer) was removed. Finally, 1mL of water was added and the organic layer (top layer)was removed. The organic layer was dried with anhydrous sodium sulfate, and then added to a vial for Gas Chromatography testing. Before conducting the experiment a prediction was made as to which free radical intermediate would be most stable and which isomer would yield the most product formation. Based on the results, it can be concluded that 1,3-dichlorobutane was both the most stable and produced the most product. This free radical intermediate was followed by 1,2-dichlorobutane, 1,4-dichlorobutane, and lastly 1,1-dichlorobutane. Based on the results 1,3-dichlorobutane produced 37% product, more than three times as much product as the least stable free radical intermediate 1,1-dichlorobutane produced. The isomer of 1,3-dichlorobutane produced the greatest yield and can be determined as the most stable free radical form of 1-chlorobutane because of the location of its free electron. The lone electron is located on a carbon with many alkyl groups surrounding it. The more groups attached to the carbon with the lone electron, the more stable of a form it is. This is a pattern seen throughout the stability rankings for the four free radical possibilities, for example when the