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JEE MAIN Chemistry QUESTION #1017
Question 1
When sec-butylcyclohexane reacts with bromine in the presence of sunlight, the major product is:
  • Bromination at the ring (cyclohexyl position)
  • Bromination at the secondary carbon of the ring giving equatorial Br
  • Bromination at the tertiary carbon of the sec-butyl chain (most stable radical)āœ”ļø
  • Bromination at the secondary carbon of the butyl chain
Correct Answer Explanation
Free radical bromination is highly selective and preferentially attacks the most stable (tertiary) radical. The sec-butyl group has a tertiary Cā€“H at the branch point. Bromine in sunlight selectively replaces the tertiary H, giving the tertiary bromide as the major product (option 3 in paper).