Problem: Why is glacial acetic acid used to react with N,N-dimethylaniline when synthesizing an azo dye, but is not used to react with salicylic acid, 1-naphthol, 2-naphthol, or 8-anilino-1-naphthalenesulfonic acid ammonium salt during the same process?

FREE Expert Solution

  • Salicylic acid, 1-naphthol, 2-naphthol, and 8-anilino-1-naphthalenesulfonic are readily activated for diazotization. 
  • Recall that 1°, 2° amines and -OH groups activate the ring.
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Problem Details

Why is glacial acetic acid used to react with N,N-dimethylaniline when synthesizing an azo dye, but is not used to react with salicylic acid, 1-naphthol, 2-naphthol, or 8-anilino-1-naphthalenesulfonic acid ammonium salt during the same process?

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