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Question 69

69 slot 2

Consider the above sequence of reactions. The number of bromine atom(s) in the final product (P) will be:

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Step 1: Bromination (Electrophilic Aromatic Substitution)

Reagent: Br₂ / FeBr₃
Reaction name: Halogenation

  • NO₂ is meta-directing
  • Bromine enters meta position

Product: m-bromonitrobenzene

Step 2: Reduction

Reagent: Sn / HCl
Reaction name: Reduction of nitro group

  • NO₂ → NH₂

Product: m-bromoaniline

Step 3: Neutralisation

  • Converts salt to free amine

Step 4: Bromination in water

Reagent: Br₂ / H₂O
Reaction name: Bromination of aniline

  • NH₂ is strongly activating → ortho & para substitution
  • Already one Br present → total becomes 3 Br added

Product: tribromoaniline derivative

Step 5: Diazotization

Reagent: NaNO₂ / HBr (0-5°C)
Reaction name: Diazotization

  • NH₂ → N₂⁺

Step 6: Sandmeyer Reaction

Reagent: CuBr / NaBr
Reaction name: Sandmeyer reaction

  • N₂⁺ → Br

Final Product (P):

  • Initially 1 Br
  • After step 4 → +3 Br = 4 Br
  • After Sandmeyer → +1 Br

Total bromine atoms = 5

Final Answer:

Number of bromine atoms = 5

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