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 24.3%.
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 | sulfuryl 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 |
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 24.3%.
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 | sulfuryl 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 |
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.