How many monochlorination products can be formed (constitutional isomers only) from the reaction of (CH₃)₂CHCH₂CH₃ with Cl₂ and hv?

Question

Quizplus · Accepted Answer

There are four potential sites of monochlorination in the given compound: the two methylene groups and the two tertiary carbons. However, only one of the tertiary carbons (centered between the two chlorine atoms) can form a stable monochlorination product due to stereoelectronic effects. Therefore, there are four possible constitutional isomers: 1-chloro-2-methylcyclohexane, 1-chloro-4-methylcyclohexane, 1-chloro-3,3-dimethylcyclohexane, and 1-chloro-4,4-dimethylcyclohexane.

How Many Monochlorination Products Can Be Formed (Constitutional Isomers Only)