Radical Chlorination of Chlorobutane

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Introduction: The radical chlorination of chlorobutane results in the formation of four possible products. These products are formed by substitution reactions, where a halogen atom (chlorine) replaces a hydrogen atom (Wade 2010). The amount of each product formed is based on the relative reactivity of the product. The calculations of the relative reactivity are dependent on the reactivity of the hydrogen atoms, which is influenced by the chloro substituent as well as other factors such as the level of the substituted carbon and the bond dissociation energy. For this lab we want to observe how the chloro substituent has an effect on the reactivity of the possible hydrogen atoms. Experimental Results The following results on the table below was not from our own experiment but was obtained through a previous lab report that was posted in aumoodle.andrews.edu for our use by Dr. Ahlberg. Products | Relative % amounts of product | Relative Reactivity= (Relative % amount/number of hydrogen on the atom with the chloro substituent) | 1,1-dichlorobutane (minor product) | 5.97% | 2.98 | 1,2-dichlorobutane (minor product) | 23.98% | 11.99 | 1,3-dichlorobutane (major product) | 47.74% | 23.87 | 1,4-dichlorobutane (minor product) | 22.28% | 7.42 | Discussion: Based on the results of our table we can see that the relative reactivity of hydrogen atoms is influenced by several factors including the chloro substituent. One factor that determines the reactivity of the hydrogen atoms is based on how highly the carbon is substituted. For free radical formation, the more highly substituted the carbon atom is (methyl > primary > secondary >tertiary), the less energy it will require (Wade 2010). However we will only be dealing with primary and secondary carbons in this report. One of the major effects that the chloro substituent has on the reactivity of hydrogen
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