- A
- B
- C
- D
View written solutionFree
Correct answer: B
- Target molecule identification
We need to prepare 4-bromo-2-nitroethyl benzene from benzene.
This is a benzene ring having:
- an ethyl group
- a bromo group para to ethyl
- a nitro group ortho to ethyl
So relative to the ethyl group, the product is:
- at para position
- at ortho position
- How to introduce the ethyl group?
Direct Friedel–Crafts alkylation with ethyl chloride is possible, but among the given options the route uses:
because Clemmensen reduction converts
So first acylation, then reduction gives ethylbenzene.
- Now decide order of bromination and nitration
From ethylbenzene:
- ethyl group is activating and ortho/para directing.
If we do bromination first:
Para product is favored due to steric reasons.
Then nitration of -bromoethylbenzene:
- ethyl is ortho/para directing, activating
- bromine is ortho/para directing, deactivating
In the para-bromoethylbenzene structure, the positions favored by both directors are the 2 and 6 positions, which are equivalent. Thus nitration gives:
This matches the target.
- Check Option B
Option B sequence:
Stepwise:
- Benzene acetophenone
- Acetophenone ethylbenzene
- Ethylbenzene mainly -bromoethylbenzene
- Nitration gives 4-bromo-2-nitroethyl benzene
So Option B is correct.
- Why other options are incorrect
Option A
After Friedel–Crafts acylation, the ring has , which is meta directing and deactivating. So bromination/nitration would not lead to the required orientation relative to ethyl after reduction. Also is not the Clemmensen reduction condition for converting aryl ketone efficiently to ethylbenzene here.
So A is incorrect.
Option C
Starting with bromobenzene, Friedel–Crafts acylation is possible but gives orientation directed by bromine; then nitration occurs in the presence of , a meta director. This does not give the desired final substitution pattern reliably. Also final is not the right reduction sequence here.
So C is incorrect.
Option D
Nitrobenzene is strongly deactivating and does not undergo Friedel–Crafts acylation. Hence this route fails.
So D is incorrect.
- Final answer
The correct sequence is:
So the correct option is B.
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