In the above conversion of compound to product , the sequence of reagents to be used will be:- A
- B
- C(i) (ii) (aq) (iii) (iv)
- D(i) (ii) (iii) (iv)
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Correct answer: C
To choose the correct reagent sequence, we identify what overall transformation is most likely being asked in this standard nitrogen-compounds conversion.
The options strongly suggest that compound is a nitro aromatic compound and product is obtained through reactions involving:
- reduction of to ,
- bromination with bromine water,
- diazotisation with ,
- and finally replacement of the diazonium group.
We now analyze each option systematically.
1. Key reactions involved
(a) Reduction of nitro group
A nitro group on benzene is reduced by to give aniline:
(b) Bromination of aniline with bromine water
Aniline is a very strong activating group and with bromine water gives tribromoaniline:
(c) Diazotisation
A primary aromatic amine reacts with nitrous acid to form diazonium salt:
(d) Reduction of diazonium salt by hypophosphorous acid
replaces the diazonium group by hydrogen:
This is a standard way to remove an amino group after using it as a directing/activating handle.
2. Examine each option
Option A
- brominates benzene/nitrobenzene type systems.
- reduces to .
- is not the standard reagent to convert the resulting aromatic amine into the likely final product here.
This sequence does not naturally lead to the common aromatic substitution/removal pattern implied by the options.
So A is incorrect.
Option B
- reacts readily with aniline/phenol, not typically the starting nitro compound.
- followed by can reduce nitro compounds, but this does not explain selective bromination and final product formation as elegantly as the diazotisation route.
So B is incorrect.
Option C
Let us trace it step by step:
-
Reduction
-
Bromination with bromine water Since is strongly activating, bromination occurs at positions, generally giving:
-
Diazotisation
So tribromoaniline becomes the corresponding tribromobenzenediazonium salt.
-
Replacement by hydrogen using
Hence the amino group is removed, leaving the brominated benzene framework.
This is a very standard synthetic route to prepare brominated benzene from nitrobenzene via aniline as an intermediate.
So C is correct.
Option D
The first three steps are same as option C, but the last step is different.
- in Sandmeyer reaction replaces diazonium group by Br, not by H.
- Therefore, this would introduce an additional bromine at the diazonium position.
So if the intended final product is obtained by removal of amino group, this option is not correct.
Hence D is incorrect.
3. Final answer
The correct sequence is:
Therefore, the correct option is:
4. Comparison with stored correct answer
Stored correct answer:
My derived answer:
So, the derived answer agrees with the stored correct answer.
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