Free radical chlorination of hexane produces this number of monochloro derivatives (including stereoisomers):
A)3
B)4
C)5
D)7
E)8

Question

Quizplus · Accepted Answer

Free radical chlorination of hexane results in the substitution of one hydrogen atom with a chlorine atom to form a monochloro derivative. Hexane has six carbon atoms, and each carbon atom can be chlorinated. However, some of the resulting monochloro derivatives may have the same structure due to the presence of stereoisomers. Therefore, the total number of different monochloro derivatives is less than six. The possible stereoisomers are cis and trans, which can occur whenever two chlorine atoms are attached to adjacent carbon atoms. Hexane has no tertiary hydrogen, so no 3-chlorohexane products are formed. Counting the possible monochloro derivatives, we get:
- 1-chlorohexane (no stereoisomer) 
- 2-chlorohexane (no stereoisomer) 
- 3-chlorohexane (no stereoisomer) 
- 4-chlorohexane (cis/trans isomers) 
- 5-chlorohexane (cis/trans isomers) 
Thus, the total number of different monochloro derivatives is 5, which is option C.

Free Radical Chlorination of Hexane Produces This Number of Monochloro