Radical Chlorination of 1-Chlorobutane.
The radical chlorination of 1-chlorobutane was carried out using sulfuryl chloride and azoisobutyronitrile (AIBN).
From the reaction there were for possible products which are as follows 1,1-dichlorobutane, 1,2- dichlorobutane, 1,3-dichlorobutane, and 1,4-dichlorobutane. The structures produced from the reaction are as follows;
Attached to the four carbons in 1-chlorobutane are hydrogens that can react readily with chlorine, because of its electron withdrawing character. Chemical environment surrounding the carbons are different and therefore affecting the character of the hydrogens attached. This difference in chemical environment finally explains the different interaction between hydrogen and chlorine.
Determination of percent yield, and relative reactivity data was processed after the products of the reaction were analyzed using Gas Chromatography. Percent yield was calculated for each isomer and determined to be; 5.94% for 1,1-dichlorobutane, 23.1% for 1,2-dichlorobutane, 47.1% for 1,3-dichlorobutane, and 23.9% for 1,4-dichlorobutane.
The relative reactivity of the hydrogens H1, H2, H3 , and H4 were 0.37, 1.4, 2.9, and 1.0 respectively.
The radical chlorination of 1-chlorobutane follows the radical reaction mechanism. Abstraction of hydrogen from 1-chlorobutane by the chlorine radical occurs in the first part of the propagation step. Depending on which hydrogen is abstracted by the chlorine radical, determines which product is formed. Hydrogens on the alkene have different reactivity which determines which isomer is favored. Hydrogens attached to carbons, and have a weak bond strength are most reactive therefore are favored during abstraction by chlorine.
The chloro substituent has an effect on carbon reactivity due to the chlorine atom being an electron withdrawing substituent. The chlorine substituent on 1-chlorobutane pulls electron density from the carbon to which it is bonded to. The...