Iodination of benzene is not easily caried out. Hov can one prepare para-iodobcnzoic acid from para-nitrotoluene?

(i) NBS in ${\mathrm{CCl}}_4$ and heat (ii) Nal in aceton (iii) $3{\mathrm{H}}_2$ and Pt or Ni catalyst (iv) ${\mathrm{HNO}}_2{0}^{\circ }\mathrm{C}$ (v) ${\mathrm{H}}_3\mathrm{P}{0}_2$

(i) ${\mathrm{Br}}_2+{\mathrm{FeBr}}_3$ (ii) Mg in ether, then ${\mathrm{CO}}_2$ {iii) $3{\mathrm{H}}_2$and Pt or Ni catalyst (iv) ${\mathrm{HNO}}_2{0}^{\circ }\mathrm{C}$(v) KI solution

(i) $\mathrm{KMn}{0}_4$ and heat (ii) $3{\mathrm{H}}_2$ and Pt or Ni catalyst (iii) ${\mathrm{HNO}}_2{0}^{\circ }\mathrm{C}$ (iv) KI solution

(i) $3{\mathrm{H}}_2$ and Pt or Ni catalyst (ii) ${\mathrm{HNO}}_2{0}^{\circ }\mathrm{C}$ (iii) ${\mathrm{Cu}}_2{\mathrm{Br}}_2+\mathrm{HBr}$ (iv) $\mathrm{KMn}{0}_4$and heat (v) KI solution