JEE Advanced · 2023 · 04 Jun 2023 · Paper 2 · Compounds Containing Nitrogen

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A trinitro compound, 1, 3,5 tris-(4-nitrophenyl) benzene, on complete reaction with an excess of gives major product, which on treatment with an excess of at provides P as the product. P, upon treatment with excess of at room temperature, gives the product . Bromination of in aqueous medium furnishes the product . The compound upon treatment with an excess of phenol under basic conditions gives the product S.

The molar mass difference between compounds and is and between compounds and is .

The number of heteroatoms present in one molecule of is ____.
[Use: Molar mass (in ):
Atoms other than C and H are considered as heteroatoms]

Answer: 9

Solution

Starting compound: 1,3,5-tris-(4-nitrophenyl)benzene has three nitro groups.
  1. Reduction with Sn/HCl converts to : gives triamine.
  1. Treatment with at 0°C forms diazonium salt P (three diazonium groups).
  1. Hydrolysis of P with replaces diazonium groups with : gives Q (triphenol).
  1. Bromination of Q in aqueous medium: each phenolic OH directs Br to ortho and para positions. With three phenol groups, we get 6 Br atoms added (2 per phenol ring). Product R has 6 Br atoms and 3 OH groups.

Heteroatoms in R:
  • 3 oxygen atoms (from OH groups)
  • 6 bromine atoms
Total = 9 heteroatoms

JEE Advanced · 2023 · 04 Jun 2023 · Paper 2 · Numerical answer

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