[alaMATngbuhay]

Hi! In our synthesis of azo dye experiment, most of the class reacted phenylammonium chloride (from mixing aniline, water, and hydrochloric acid) with nitric acid instead of using nitrous acid. When we mixed this solution with naphthol (dissolved in sodium hydroxide) and filtered it out, we produced a light brown, pinkish solid residue (akin to the color of liver spread) instead of a deep dark red dye produced by groups that utilized nitrous acid instead. What product did the nitric acid groups form in the end, and what reactions took place?

[chenbeier]

Probably you get only a nitration of the Phenylgroup to Nitro-aniline.  Azo will not be formed, because there is no reduction.

[alaMATngbuhay]

Probably you get only a nitration of the Phenylgroup to Nitro-aniline.  Azo will not be formed, because there is no reduction.

So when I subsequently reacted nitroaniline with (a)-naphthol, what was the pale, pinkish powder formed? 

[AWK]

Which compound can be nitrated more easily, aniline hydrochloride or naphthol?

[rolnor]

You would get much information from running TLC. The precipitate can be misscolored startingmaterial.