JEE Advanced levelSingle correct optionDifficulty 3 of 3o2048
Vinylcyclohexane, CX6HX11−CH=CHX2, reacts with HCl (no peroxide). Taking the most stable carbocation reachable by a 1,2-shift, the major product is
A1-chloro-1-ethylcyclohexane
B1-chloro-2-ethylcyclohexane
C(2-chloroethyl)cyclohexane
D(1-chloroethyl)cyclohexane
Answer: A
Protonation gives the secondary cation CX6HX11−CHX+−CHX3. 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.