Match the following:
(i)-(b), (ii)-(c), (iii)-(d), (iv)-(e), (v)-(a)
(i) Introduction of Br on the ring of 4-nitrotoluene (ortho to the activating \(\mathrm{CH_3}\)) is electrophilic bromination: \(\mathrm{Br_2}\) → (b).
(ii) \(\mathrm{NO_2\rightarrow NH_2}\) is reduction: \(\mathrm{Sn/HCl}\) → (c).
(iii) \(\mathrm{Ar{-}NH_2\rightarrow Ar{-}N_2Cl}\) is diazotisation: \(\mathrm{NaNO_2/HCl}\), 273–278 K → (d).
(iv) \(\mathrm{Ar{-}N_2Cl\rightarrow Ar{-}H}\) is replacement by hydrogen: \(\mathrm{H_2O/H_3PO_2}\) → (e).
(v) \(\mathrm{Ar{-}CH_3\rightarrow Ar{-}COOH}\) is side-chain oxidation: \(\mathrm{KMnO_4/OH^-}\) → (a).
Hence, (i)-(b), (ii)-(c), (iii)-(d), (iv)-(e), (v)-(a).
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