Question

How many $C_6{H}_3{ClBrNO}_2$ isomers may be produced by bromination of meta-chloronitrobenzene?

• A. 1
• B. 2
• C. 3
• D. 4

Answer 1

Answer: (D)

4

When meta-chloronitrobenzene reacts with bromine, then bromination can occur at all the vacant positions on the benzene ring.

Nitro group is meta-directing, therefore, the incoming electrophile, bromonium ion, can be substituted at the meta-position.

Chloro group is an ortho and para directing, therefore, the incoming electrophile, bromonium ion, can be substituted at the ortho and para-positions to the chloro group.

Therefore, four isomeric products will be formed on bromination of meta-chloronitrobenzene.

The bromination of meta-chloronitrobenzene is shown above.

Hence, the correct option is $\text{D}$