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ChemistryInteger+4 / -1Question 75 of 75

JEE Main 2026 · 2 Apr · Shift 2, Chemistry question 75

Consider the following reactions sequence

When the product (P) is subjected to Carius analysis using AgNOX3\ce{AgNO3}, 1.0 g of the product (P) will produce ________ g of the precipitate of AgBr. (Nearest Integer)
(Given : molar mass in g mol−1^{-1} C : 12, H : 1, O : 16, N : 14, Br : 80, Ag : 108)

4-Nitrotoluene treated with (i) Sn/HCl; OH⁻ (ii) (CH₃CO)₂O (iii) Br₂/AlBr₃ (iv) H₃O⁺ gives the major product (P).
Answer and worked solution

Official answer: 1

Sequence.

  • Sn/HCl reduces 4-nitrotoluene to p-toluidine.
  • Acetylation gives 4-methylacetanilide.
  • Bromination puts Br ortho to −NHCOCHX3\ce{-NHCOCH3} (the stronger director).
  • Acid hydrolysis frees the amine: P = 2-bromo-4-methylaniline, CX7HX8BrN\ce{C7H8BrN} (186 g mol⁻¹).

Carius. 1.0 g of P has 1186\frac1{186} mol Br, giving 188186=1.01\frac{188}{186}=1.01 g AgBr. Nearest integer: 1.

Answer: 1

Topics:AminesQualitative and quantitative analysis of organic compounds
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