JEE PYQ: Haloalkanes And Haloarenes Question 29
Question 29 - 2019 (12 Jan Shift 1)
The major product of the following reaction is:
A steroid-like bicyclic compound with exocyclic $\text{C}(\text{CH}_3)=\text{CH}_2$ $\xrightarrow{\text{HCl}}$
(1) $\text{CH}_2\text{Cl}$ on ring with $\text{CH}_3$ and H
(2) Cl on ring with two $\text{CH}_3$ groups
(3) $\text{CH}_2\text{Cl}$ at exocyclic position
(4) Tertiary Cl product with $\text{CH}_3$ groups
Show Answer
Answer: (4)
Solution
HCl addition follows Markovnikov rule. The more substituted carbocation (tertiary) is formed, which gets attacked by Cl$^-$ to give the tertiary chloride product.