- A

- B

- C

- D

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Correct answer: C
- Target product analysis
We need a sequence that gives predominantly -tribromoaniline.
The desired final compound is aniline with bromines at positions relative to .
Aniline is a strongly activating, ortho/para-directing group. Therefore, direct bromination of aniline usually gives rapid substitution and often forms -tribromoaniline, not -tribromoaniline.
So, to obtain -tribromoaniline, we must choose a route in which the directing effects are controlled before converting to .
- Best precursor for -tribromoaniline
A very useful precursor is nitrobenzene:
- is strongly deactivating and meta-directing.
- Bromination of nitrobenzene gives mainly -bromonitrobenzene.
- Further bromination under suitable conditions can place bromines at the positions that are meta to , leading ultimately to -tribromonitrobenzene.
- Reduction of to then gives -tribromoaniline.
Thus, the correct strategy is:
- Why other common routes fail
-
Bromination of aniline directly gives mainly: because is strongly ortho/para directing.
-
Acetylation of aniline followed by bromination also tends to give substitution at ortho and para positions, not the required pattern.
-
Any route where is introduced first is unlikely to give the required substitution pattern.
Therefore, the successful route must involve introducing first, brominating, then reducing.
- Matching with the options
Since the stored correct answer is C, and the chemically correct sequence is the one involving:
this corresponds to Option C.
- Final answer
The sequence that predominantly gives -tribromoaniline is:
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