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An isomer of nitrotoluene undergoes the following sequence of reactions to yield 4-chlorobenzoic acid as the final major product: 1. Cl ₂ / FeCl ₃ 2. Fe / HCl 3. NaNO ₂ / HCl , 0-5^ C 4. H ₃ PO ₂ / H ₂ O 5. Alk. KMnO ₄, followed by H ₃ O ^+ Identify the starting isomer of nitrotoluene.

Options

  1. Ap -nitrotoluene
  2. Bm -nitrotoluene
  3. Co -nitrotoluene
  4. D2,4-dinitrotoluene

Correct answer

C. o -nitrotoluene

Step-by-step solution

Working backwards from the final product: The final product is 4-chlorobenzoic acid. Step 5 (oxidation with alkaline KMnO ₄ ) oxidizes an alkyl side chain to a - COOH group. Thus, the precursor before oxidation must be 4-chlorotoluene. 4-chlorotoluene is formed in Step 4 via reductive deamination of a diazonium salt using H ₃ PO ₂ . This means the original nitrotoluene isomer must have undergone chlorination to place the chlorine atom para to the methyl group. Let us evaluate the isomers of nitrotoluene: - In p -ni

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