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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2048

Vinylcyclohexane, , reacts with HCl (no peroxide). Taking the most stable carbocation reachable by a 1,2-shift, the major product is

  1. A1-chloro-1-ethylcyclohexane
  2. B1-chloro-2-ethylcyclohexane
  3. C(2-chloroethyl)cyclohexane
  4. D(1-chloroethyl)cyclohexane

Answer: A

Protonation gives the secondary cation . A 1,2-hydride shift from the ring carbon attached to it gives the tertiary 1-ethylcyclohexyl cation. Chloride adds to give 1-chloro-1-ethylcyclohexane as the major product.
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