3
Question
Which is the major monobromination product when ethylcyclohexane is subjected to free radical bromination?
Which is the major monobromination product when ethylcyclohexane is subjected to free radical bromination?
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Solution
The correct option is D
Free radical bromination reaction is highly selective, occurs mainly at the carbon where most stable free radical is formed.
We know that the stability of free radical is in the order,
Tertiary radical > Secondary radical > Primary radical
In (a), (b) and (c), the bromination occurs at secondary carbon whereas in (d) the bromination occurs at tertiary carbon. Since, tertiary radicals are more stable than secondary radical the major product of monobromination of ethyl cyclohexane is (d).
The stability of tertiary radical is due to the higher number of α−Hygrogens which give more hyperconjugation effect than secondary.
Free radical bromination reaction is highly selective, occurs mainly at the carbon where most stable free radical is formed.
We know that the stability of free radical is in the order,
Tertiary radical > Secondary radical > Primary radical
In (a), (b) and (c), the bromination occurs at secondary carbon whereas in (d) the bromination occurs at tertiary carbon. Since, tertiary radicals are more stable than secondary radical the major product of monobromination of ethyl cyclohexane is (d).
The stability of tertiary radical is due to the higher number of α−Hygrogens which give more hyperconjugation effect than secondary.
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