JEE Challenger
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Total Bromine Atoms in Compound T Synthesis Scheme

Schemes 1 and 2 outline the reaction steps to yield QQ from PP and SS from RR, respectively. Scheme 3 demonstrates the synthesis of product TT using QQ and SS. Determine the overall number of Br\text{Br} atoms contained in one molecule of TT.

Question Diagram 1
Official Numerical Answer4

Step-by-Step Solution

To determine the total number of bromine (Br\text{Br}) atoms in one molecule of compound TT, we trace the step-by-step chemical transformations in each scheme:

Scheme 1: Synthesis of Compound QQ

  1. Reactant PP: Aniline (C6H5NH2\text{C}_6\text{H}_5\text{NH}_2).
  2. Step (i): Reaction with Br2 (excess),H2O\text{Br}_2 \text{ (excess)}, \text{H}_2\text{O}
    • The amino group (−NH2-\text{NH}_2) is strongly activating, and in aqueous medium, it undergoes electrophilic aromatic substitution to form 2,4,6-tribromoaniline (contains 33 Br atoms).
  3. Step (ii): Reaction with NaNO2,HCl,273 K\text{NaNO}_2, \text{HCl}, 273\text{ K}
    • Diazotization converts the −NH2-\text{NH}_2 group to a diazonium salt, yielding 2,4,6-tribromobenzenediazonium chloride.
  4. Step (iii): Reaction with CuCN/KCN\text{CuCN/KCN}
    • Sandmeyer reaction replaces the diazonium group (−N2+-\text{N}_2^+) with a cyano group (−CN-\text{CN}), forming 2,4,6-tribromobenzonitrile.
  5. Step (iv): Reaction with H3O+,Δ\text{H}_3\text{O}^+, \Delta
    • Acid hydrolysis converts the cyano group (−CN-\text{CN}) into a carboxylic acid group (−COOH-\text{COOH}), yielding 2,4,6-tribromobenzoic acid.
  6. Step (v): Reaction with SOCl2,pyridine\text{SOCl}_2, \text{pyridine}
    • Chlorination converts the carboxylic acid into an acyl chloride, yielding 2,4,6-tribromobenzoyl chloride as the major product QQ.

Number of Br\text{Br} atoms in compound Q=3Q = 3


Scheme 2: Synthesis of Compound SS

  1. Reactant RR: Benzene (C6H6\text{C}_6\text{H}_6).
  2. Step (i): Reaction with Oleum\text{Oleum}
    • Sulfonation yields benzenesulfonic acid (C6H5SO3H\text{C}_6\text{H}_5\text{SO}_3\text{H}).
  3. Steps (ii) & (iii): Reaction with NaOH,Δ\text{NaOH}, \Delta followed by H+\text{H}^+
    • Alkali fusion followed by acidification converts benzenesulfonic acid to phenol (C6H5OH\text{C}_6\text{H}_5\text{OH}).
  4. Step (iv): Reaction with Br2,CS2,273 K\text{Br}_2, \text{CS}_2, 273\text{ K}
    • Electrophilic bromination of phenol in a non-polar solvent (CS2\text{CS}_2) at low temperature selectively yields 4-bromophenol (para-bromophenol) as the major product SS.

Number of Br\text{Br} atoms in compound S=1S = 1


Scheme 3: Synthesis of Compound TT

  1. Step (i): Reaction of SS (4-bromophenol) with NaOH\text{NaOH}
    • Deprotonation forms sodium 4-bromophenoxide.
  2. Step (ii): Reaction of sodium 4-bromophenoxide with QQ (2,4,6-tribromobenzoyl chloride)
    • Nucleophilic acyl substitution results in the formation of an ester, 4-bromophenyl 2,4,6-tribromobenzoate as the major product TT.

Conclusion:

Compound TT consists of:

  • 33 bromine atoms from the 2,4,6-tribromobenzoyl moiety (QQ)
  • 11 bromine atom from the 4-bromophenoxy moiety (SS)

Total number of Br atoms in T=3+1=4\text{Total number of Br atoms in } T = 3 + 1 = 4