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

Question

Quizplus · Accepted Answer

The compound given has 4 methylene (CH2) groups. Each of these can potentially be chlorinated, leading to different constitutional isomers. However, two of these methylene groups are indistinguishable due to symmetry in the molecule, leading to identical products.
Thus, 3 constitutional isomers can be formed: 
1) 1-chloro-2,3-dimethylcyclohexane
2) 1-chloro-3,4-dimethylcyclohexane
3) 1-chloro-2,4-dimethylcyclohexane
Therefore, the answer is (C) 4.

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