Which of the following compounds can be prepared by free radical halogenation without compIication by formation of isomeric by-products?

Options

A.
B.
C.
D.

Answer

C

Explanation

In cyclopentane, all hydrogen atoms are equivalent, so only one product is produced on chlorination.
Although bromination is more selective than chlorination for substitution of particular hydrogen atom, but 1 ,4-dimethylcyclohexane contains `1^(@) , 2^(@)` and `3^(@)` hydrogen atoms out of which `2^(@)` and `3^(@)` hydrogen atoms would participate in the reaction and mixture of isomers is produced
n-pentane also contains two types of `2^(@)` hydrogen atoms, so, a mixture of at least two isomeric fonns is produced.
In the case of bromination of 2-methylliexane, mixture of structural as well as optical isomers is produced since it contains `2^(@)` and `3^(@)` hydrogen atoms for bromination.