Iodination of benzene is not easily caried out. How can one prepare para-iodobenzoic acid from para-nitrotoluene? Note: HNO2 = NaNO2 + 10% H2SO4

Engineering

Chemistry

Aromatic Nucleophilic Substitution

Electrophilic substitution

Question

Iodination of benzene is not easily caried out. How can one prepare para-iodobenzoic acid from para-nitrotoluene?
Note: HNO₂ = NaNO₂ + 10% H₂SO₄

(i) Sn + HCl (ii) HNO₂ 0ºC (iii) Cu₂Br₂ + HBr (iv) KMnO₄ & heat (v) KI solution.

(i) KMnO₄ & heat (ii) 3 H₂ & Pt or Ni catalyst (iii) HNO₂ 0ºC (iv) KI solution

(i) Br₂ + FeBr₃ (ii) Mg in ether, then CO₂ (iii) 3 H₂ & Pt or Ni catalyst (iv) HNO₂ 0ºC (v) KI solution

(i) NBS in CCl₄ & heat (ii) NaI in acetone (iii) 3 H₂ & Pt or Ni catalyst (iv) HNO₂ 0ºC (v) H₃PO₂

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