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Correct answer: 51
- Starting compound and reduction
The given compound is 1,3,5-tris-(4-nitrophenyl)benzene.
It has three para-nitrophenyl groups attached to a central benzene ring.
On complete reduction with excess , each group is converted into .
So the major product is:
- Formation of
Treatment with excess at diazotizes each amino group:
Hence is the tris-diazonium chloride derivative.
So contains 3 diazonium groups.
- Formation of from
Diazonium salt on treatment with excess water at room temperature gives phenol:
Thus is:
So has 3 phenolic rings, each para-substituted.
- Formation of by bromination of
A phenolic ring strongly activates bromination at the ortho positions to .
In each -substituted phenol ring, the para position is already occupied by linkage to the central benzene ring, so bromination occurs at the two ortho positions.
Thus each outer ring gets 2 bromine atoms.
There are 3 such rings, so total bromines introduced:
Mass increase from to per bromination is replacement of H by Br:
For 6 brominations:
This matches the given data, confirming the structure.
- Formation of from with phenol/basic medium
Diazonium salts couple with phenol in basic medium to give azo compounds.
Each diazonium group couples with one phenol molecule.
Since has 3 diazonium groups, is formed by coupling with 3 phenol molecules.
The mass difference between and is given as .
Let us verify per coupling.
For one coupling:
- one phenol unit added: , mass
- one H is lost from phenol ring during coupling:
- diazonium group loses ? No, in azo coupling the diazonium group becomes , so the two nitrogens remain in product.
- chloride ion is not part of covalent structure of product.
So net increase per diazonium group from diazonium salt to azo-coupled product is:
For 3 groups:
So indeed all 3 diazonium groups couple with phenol.
Hence is the tris-azo coupled product with 3 phenol units.
- Count carbon atoms in
Initial skeleton in starting trisubstituted benzene after diazotization still has:
- central benzene ring: carbons
- three outer phenyl rings: carbons
So in (and retained in ):
Now 3 phenol molecules couple, each contributes one phenyl ring:
Total carbons in :
- Count heteroatoms in
Heteroatoms are atoms other than C and H.
In :
- each azo linkage contributes nitrogen atoms
- there are azo linkages
So nitrogen atoms:
Each coupled phenol unit retains one oxygen atom:
Total heteroatoms:
- Total number of carbon atoms and heteroatoms in
Therefore, the required integer is:
- Comparison with stored correct answer
Stored correct answer = .
Our derived answer also is , so they agree.
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