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Radical Chlorination Of 1-Chlorobutane Lab Report

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Radical Chlorination of 1-Chlorobutane Stella Greathouse March 3, 2023 Abstract A light-initiated reaction between sodium hypochlorite and hydrochloric acid was done to carry out the radical chlorination of 1-chlorobutane. The product was then extracted using sodium bicarbonate and dried using anhydrous sodium sulfate. The amount of each dichlorobutane product was then found through gas chromatography analysis. These amounts then helped to determine the relative reactivities of the hydrogens in the products and the effect of the chloro-substituent on the relative rate of hydrogen abstraction, which is the rate determining step. Overall, this report will present the data for the radical chlorination of 1-chloro butane and explain why 1,4-dichlorobutane …show more content…

The relative reactivity was found by setting the reactivity per hydrogen of 1,4-dichlorobutane to 1.0. As shown in Figure 4, 1,3 dichlorobutane had the highest yield of 48% and the highest relative reactivity of 3. This is because it replaced the C-H bond that was furthest from the chloro substituent and formed a stable secondary intermediate. Next, 1,4-dichlorobutane had the second highest yield of 24%, but the third lowest reactivity of 1.0. Even though it was the furthest C-H bond from the chloro substituent, it formed a less stable primary radical intermediate. This caused it to have a lower reactivity. However, the farther distance from the chloro substituent and the greater number of hydrogens it could replace during hydrogen abstraction (3 from the methyl group), caused it to have the second highest yield. The third highest yield of 22% and the second highest reactivity of 1.4 was 1,2-dichlorobutane. 1,2-dichlorobutane had a smaller yield because it was closer to the chloro substituent. However, since it formed a secondary radical intermediate, it had a higher reactivity. 1,1-dichlorobutane had the smallest yield of 5.5% and the smallest reactivity of 0.38. Even though it formed a stable secondary radical intermediate, it was directly attached to the chloro substituent. Altogether, the data showed two trends: more stable radical intermediates and a greater distance from the chloro substituent increase the relative yield and relative

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