When butane reacts with Br₂ in the presence of Cl₂, both brominated and chlorinated products are obtained. Under such conditions, the usual selectivity of bromination is not observed. In other words, the ratio of 2-bromobutane to 1-bromobutane is very similar to the ratio of 2-chlorobutane to 1-chlorobutane. Can you offer and explanation as to why we do not observe the normal selectivity expected for bromination? Chlorine radicals perform the first propagation step (hydrogen abstraction) comparison to bromine radicals. Under these conditions in radicals form easily in the presence of chlorine radicals. Subsequently, the resulting radicals can react with bromine in a second propagation step to yield monobrominated products.

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When butane reacts with Br₂ in the presence of Cl₂, both
brominated and chlorinated products are obtained. Under such
conditions, the usual selectivity of bromination is not observed. In
other words, the ratio of 2-bromobutane to 1-bromobutane is very
similar to the ratio of 2-chlorobutane to 1-chlorobutane. Can you
offer and explanation as to why we do not observe the normal
selectivity expected for bromination?
Chlorine radicals perform the first propagation step (hydrogen
abstraction)
comparison to bromine radicals. Under these conditions
in
radicals form easily in the presence of
chlorine radicals. Subsequently, the resulting radicals can react with
bromine in a second propagation step to yield monobrominated
products.
Transcribed Image Text:When butane reacts with Br₂ in the presence of Cl₂, both brominated and chlorinated products are obtained. Under such conditions, the usual selectivity of bromination is not observed. In other words, the ratio of 2-bromobutane to 1-bromobutane is very similar to the ratio of 2-chlorobutane to 1-chlorobutane. Can you offer and explanation as to why we do not observe the normal selectivity expected for bromination? Chlorine radicals perform the first propagation step (hydrogen abstraction) comparison to bromine radicals. Under these conditions in radicals form easily in the presence of chlorine radicals. Subsequently, the resulting radicals can react with bromine in a second propagation step to yield monobrominated products.
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