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Although methylcyclohexane can react with bromine to form a synthetically useful

ID: 867375 • Letter: A

Question

Although methylcyclohexane can react with bromine to form a synthetically useful tertiary halide as shown below, its reaction with chlorine does not produce a synthetically useful tertiary halide. Choose the statement that best explains the reaction of methylcyclohexane with chlorine. The reaction of methylcyclohexane with chlorine does not form a tertiary halide as one of the products. The reaction of methylcyclohexane with chlorine is endothermic because carbon-chlorine bonds are weaker than carbon- hydrogen bonds. The reaction of methylcyclohexane with chlorine is too slow to be of synthetic utility because the rate-determining step has a high activation barrier. The reaction of methylcyclohexane with chlorine is not selective and forms a mixture of chlorinated derivatives of methylcyclohexane. Chlorine radicals are more reactive than bromine radicals. In fact, because the H- Br bond is weaker than the H-Cl bond, one would expect the halogen radical abstraction of a hydrogen to have a higher activation barrier in the case of bromine.

Explanation / Answer

Best explain is "The reaction of methylcyclohexane with chlorine is not selective and forms a mixture of chlorinated derivatives of methylcyclohexane."

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