A trinitro compound, 1,3,5-tris-(4-nitrophenyl)benzene, on complete reaction with an excess of Sn/HCl gives a major product, which on treatment with an excess of NaNO/HCl at 0°C provides P as the product. P, upon treatment with excess of HO at room temperature, gives the product Q. Bromination of Q in aqueous medium furnishes the product R. The compound P upon treatment with an excess of phenol under basic conditions gives the product S.
The molar mass difference between compounds Q and R is 474 g mol−1 and between compounds P and S is 172.5 g mol−1.
The total number of carbon atoms and heteroatoms present in one molecule of S is:
[Use: Molar mass (in g mol−1): H = 1, C = 12, N = 14, O = 16, Br = 80, Cl = 35.5. Atoms other than C and H are considered as heteroatoms.]
Correct Answer :
Solution :
The correct answer is 51.
Step-by-Step Reaction Sequence and Analysis:
1. Starting Material:
The starting compound is 1,3,5-tris-(4-nitrophenyl)benzene. It consists of a central benzene ring attached to three 4-nitrophenyl groups at the 1, 3, and 5 positions. Its molecular formula is .
2. Reduction with Sn/HCl:
Treating the trinitro compound with an excess of Sn/HCl reduces all three nitro groups (-NO2) to primary amino groups (-NH2). The product formed is 1,3,5-tris-(4-aminophenyl)benzene.
3. Diazotization to form Compound P:
Reaction of 1,3,5-tris-(4-aminophenyl)benzene with an excess of NaNO2/HCl at 0°C converts all three amino groups into diazonium chloride groups (-N2+Cl-).
Thus, Compound P is 1,3,5-tris-(4-diazoniophenyl)benzene tri-chloride, which has 3 diazonium salt groups.
Molecular formula of P: .
4. Formation of Compound Q (Hydrolysis):
When P is treated with excess water (H2O) at room temperature, all three diazonium groups are hydrolyzed to phenolic hydroxyl groups (-OH).
Thus, Compound Q is 1,3,5-tris-(4-hydroxyphenyl)benzene, having 3 phenol groups.
Molecular formula of Q: .
5. Bromination to form Compound R:
Bromination of Q in aqueous medium leads to polybromination of the activated aromatic rings containing the -OH groups. Each phenolic ring has two ortho-positions relative to the -OH group that get brominated.
Since there are 3 such rings, a total of 6 bromine atoms are introduced (2 Br per phenolic ring).
Molecular formula of R: .
Verification of molar mass difference between Q and R:
Each bromination replaces a -H with -Br, causing a mass increase of (80 - 1) = 79 g mol-1 per site.
For 6 sites: g mol-1, which matches the given difference of 474 g mol-1.
6. Formation of Compound S (Azo Coupling):
Compound P (tris-diazonium salt) reacts with an excess of phenol under basic conditions to undergo an azo coupling reaction at the para-position of each phenol molecule.
Since P has 3 diazonium groups, it couples with 3 phenol molecules to form an tris-azo dye.
Structure of Compound S: Central 1,3,5-triphenylbenzene core attached via 3 azo linkages (-N=N-) to 3 phenol rings at their para-positions.
Verification of Molar Mass Difference between P and S:
Compound P: (Molar Mass = g mol-1)
Compound S: (Molar Mass = g mol-1)
Mass Difference = g mol-1, which perfectly matches the given value.
7. Calculating Carbon and Heteroatoms in Compound S:
Molecular formula of Compound S is .
• Number of Carbon (C) atoms = 42
• Heteroatoms are atoms other than C and H, which are Nitrogen (N) and Oxygen (O).
• Number of Nitrogen (N) atoms = 6
• Number of Oxygen (O) atoms = 3
• Total number of heteroatoms =
Therefore, the total number of carbon atoms and heteroatoms present in one molecule of S is:
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