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Radical Chlorination of 1-Chlorobutane

CHE 213-451 11-1-11 Title: Radical Chlorination of 1-Chlorobutane Abstract: The purpose of the lab is to form 4 different dichlorobutanes by reacting chlorine radicals with 1-chlorobutane. This is then analyzed by gas chromatography to determine the experimental abundance of each isomer. Results: 1,1-dichlorobutane had an experimental abundance of 5. 9%, 1,2-dichlorobutane had an experimental abundance of 21. 1%, 1,3-dichlorobutane had an experimental abundance of 48. 7%, 1,4-dichlorobutane had an experimental abundance of 24. %. Procedure: Williamson and Masters, Pages 330-331. Discussion: CH2Cl-CH2-CH2-CH3 CH2Cl-CH2-CH2-CH3 CH2Cl-CHCl-CH2-CH3 CH2Cl-CHCl-CH2-CH3 CHCl2-CH2-CH2-CH3 CHCl2-CH2-CH2-CH3 Reaction SO2Cl2 + 1-chlorobutane 1,1-dichlorobutane 1,2-dichlorobutane CH2Cl-CH2-CH2-CH2Cl CH2Cl-CH2-CH2-CH2Cl CH2Cl-CH2-CHCl-CH3 CH2Cl-CH2-CHCl-CH3 + + 1,3-dichlorobutane 1,4-dichlorobutane Compound| Boiling Point (°C)| Density (g/mL)| 1-chlorobutane| 77-78| 0. 886| ulfuryl chloride | 69| 1. 67| 1,1-dichlorobutane| 114| 1. 0863| 1,2-dichlorobutane| 124| 1. 112| 1,3-dichlorobutane| 134| 1. 115| 1,4-dichlorobutane| 162| 1. 16| The greater the boiling point, the greater the retention time. The peaks are ordered as 1-chlorobutane first, then 1,1-dichlorobutane, 1,2-dichlorobutane, 1,3-dichlorobutane, and 1,4-dichlorobutane last. The 1-chlorobutane is first because it has the lowest boiling point, while 1,4-dichlorobutane is last because it has the highest boiling point.

Isomer| Type of Cwith 2nd Cl| # of H’s on C with 2nd Cl before rxn| Experimental % Abundance| Relative Abundance, ra| 1,1-dichlorobutane| 1°| 2| 5. 9| 3. 0| 1,2-dichlorobutane| 2°| 2| 21. 1| 10. 6| 1,3-dichlorobutane| 2°| 2| 48. 7| 24. 4| 1,4-dichlorobutane| 1°| 3| 24. 3| 8. 10| Relative Abundance (ra) for each C Isomer| C 1| C 2| C 3| C 4| | # of Equivalent H| ra| # of Equivalent H| ra| # of Equivalent H| ra| # of Equivalent H| ra| 1,1-dichlorobutane| 1| 5. 9| 2| 3. 0| 2| 3. 0| 3| 2. 0| 1,2-dichlorobutane| 2| 10. 6| 1| 21. 2| 2| 10. 6| 3| 7. 0| 1,3-dichlorobutane| 2| 24. | 2| 24. 4| 1| 48. 7| 3| 16. 2| 1,4-dichlorobutane| 2| 12. 2| 2| 12. 2| 2| 12. 2| 2| 12. 2| Sample Calculations: 1. 36915 + 4. 88658 + 11. 28018 + 5. 62592 = 23. 16183 Experimental Abundance 1. 36915 x 100 = 5. 9% 23. 16183 Relative Abundance 5. 9 = 3. 0 2 Lessons Learned: Pay better attention when taught how to clean the syringe… References: Williamson, Kenneth L. and Katharine M. Masters. Macroscale and Microscale Organic Experiments: Anne Arundel Community College Edition. 6th ed. 2011. Ziolkowski, Courtney. CHE 213 Lab Notebook. 1 Nov. 2011.

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