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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.


Learning Progress: Step 29 of 29 in this series