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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc091

Match the coupling partner and conditions in List I with the azo product in List II. List I: (P) phenol, pH 9-10; (Q) aniline, pH 4-5; (R) 2-naphthol, aqueous NaOH; (S) N,N-dimethylaniline, pH 4-5. List II: (1) 4-aminoazobenzene; (2) 4-hydroxyazobenzene; (3) 1-(phenylazo)-2-naphthol; (4) 4-(dimethylamino)azobenzene.

  1. AP-1, Q-2, R-3, S-4
  2. BP-2, Q-4, R-3, S-1
  3. CP-3, Q-1, R-2, S-4
  4. DP-2, Q-1, R-3, S-4

Answer: D

Phenoxide couples para to give 4-hydroxyazobenzene (P-2); aniline at pH 4-5 gives 4-aminoazobenzene (Q-1); 2-naphthoxide couples at C-1 (R-3); N,N-dimethylaniline gives 4-(dimethylamino)azobenzene (S-4). Benzenediazonium chloride is the diazonium component in all cases.
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