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In the given reaction of aniline, a coloured product, C was obtained. Predict the structure of C.

Question and options

In the given reaction of aniline, a coloured product, C was obtained. Predict the structure of C.
Figure
  1. Figure
    C6H5−NH−NH−C6H4−N(CH3)2\mathrm{C_6H_5{-}NH{-}NH{-}C_6H_4{-}N(CH_3)_2} (para; hydrazo compound)
  2. Figure
    C6H5−N=N−C6H4−N(CH3)2\mathrm{C_6H_5{-}N{=}N{-}C_6H_4{-}N(CH_3)_2} (para; 4-(dimethylamino)azobenzene)
  3. Figure
    C6H5−N=N−CH2−N(CH3)−C6H5\mathrm{C_6H_5{-}N{=}N{-}CH_2{-}N(CH_3){-}C_6H_5}
  4. Figure
    2−CH3C6H4−N=N−C6H4−2−CH3\mathrm{2{-}CH_3C_6H_4{-}N{=}N{-}C_6H_4{-}2{-}CH_3} (2,2'-dimethylazobenzene)

Answer and explanation

Correct answer: B - \(\mathrm{C_6H_5{-}N{=}N{-}C_6H_4{-}N(CH_3)_2}\) (para; 4-(dimethylamino)azobenzene)
Aniline + NaNO2/HCl\mathrm{NaNO_2/HCl} gives benzenediazonium chloride (B), which couples at the para position of N,N-dimethylaniline to give p-(dimethylamino)azobenzene (butter yellow). The hydrazo compound is a reduced product, the N-CH2 structure is a triazene-type N-alkyl product and 2,2'-dimethylazobenzene is an unrelated azotoluene.

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