[black_squirrel]

Okay so i'm kinda stuck. I reacted benzylamine with CrO3 in H2SO4 (Jones Test). The orange color of chromic acid remained but I also got a little bit of white precipitate.

So i know that CrO3 should oxidize the benzylic carbon to a ketone and keep the -NH2 intact. Is that the white precipitate I saw?

[Butyllithium]

Hi,man...You mean that benzylamine was transfomed to phenyl formaide after oxidized by Jones eagent?
If it worked, that will be a great idea!!! Have you ever analyzed it or them you had got?
In fact, I dont think you have got the desired compound. Electron density on N is largely more than carbnon, so I think -NH2 will be oxidized primarily, to produce nitroso or nitro or other intermediates. The precipitate you have got may be single compound or mixture. That's all, thx.

[shelanachium]

I think you got benzoic acid which has limited water-solubility. Oxidation of C6H5CH2NH2 by CrO3 like that of C6H5CH2OH (benzyl alcohol) no oxidation of the nitrogen.

[black_squirrel]

this is what i think happened and it matches physical observations. is this a no go?

[ARGOS++]

Dear Black_Squirrel;

I have not only a little trouble to believe in “your” mechanism, because it is (at least for me) more common, that –NH₂ group is much more reactive as any –CH₂ group.
Therefore I agree with Shelanachium with the only exception, that the –NH₂ group is prior oxidised to at least N₂ and finally the remaining carbon is oxidised similar to the production of Benzoic Acid from Toluene.

But the physically data (Bp, UV-Spectrum, IR, etc.) should be enough different for Identification.

Good Luck!
                   ARGOS⁺⁺

[black_squirrel]

i didn't see any gas evolution..? But yeah, benzoic acid makes more sense. Thank you all.