Radical Chlorination of 1-Chlorobutane

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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|...
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