1-Chlorobutane and (S)-2-Chlorobutane C4H9Cl

Section 9.3. Product distribution in chlorination.

The two monochlorinated isomers produced by radical reaction of butane with chlorine. Statistically, the ratio of product amounts expected, calculated from the ratio of different hydrogen atoms in butane, is 60% of the primary isomer and 40% of the secondary isomer. The experimentally found ratio is 29% 1-chlorobutane and 71% 2-chlorobutane. The difference between the statistically expected result and the experimental result is explained by the lower energy of the secondary radical, leading to a lower energy for the transition state and a faster rate of production than for the primary radical.


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File created Tue Feb 11 12:19:02 2003