
- A
- B
- C
- D
View written solutionFree
Correct answer: C
- Target transformation
We need to convert nitrobenzene to m-dibromobenzene.
Nitrobenzene already has one substituent: . The nitro group is:
- strongly deactivating
- meta-directing
So if we brominate nitrobenzene first, bromine will enter the meta position, giving m-bromonitrobenzene. After that, if we convert the group into , we will obtain 1,3-dibromobenzene (m-dibromobenzene).
So the logical sequence is:
This is the Sandmeyer route.
- Check each option
Option A
This starts directly with diazotization reagents. But nitrobenzene is not an amine, so it cannot be diazotized directly.
So A is incorrect.
Option B
- reduces nitrobenzene to aniline.
- Then alone does nothing useful here.
- Also, bromination of aniline is not suitable for obtaining the required meta product; aniline is ortho/para directing and highly activating.
So B is incorrect.
Option C
Stepwise:
-
Bromination because is meta-directing.
-
Reduction of nitro group
-
Diazotization
-
Sandmeyer reaction
This gives the desired product.
So C is correct.
Option D
- converts nitrobenzene to aniline.
- Bromination of aniline gives mainly 2,4,6-tribromoaniline, not the desired meta-bromo derivative.
- Also, diazotization requires acidic medium, and alone is not the proper Sandmeyer reagent.
So D is incorrect.
- Final answer
The correct reagent sequence is:
Hence, the correct option is C.
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