[gkasparis]

i have added concentrated nitric acid to ferrocene. i noticed some fumes, at the beginning ( little HNO₃) the solution turned light blue and the ferrocene was insoluble ( majority if not all of it), when more acid was added the solution turned dark blue-greenish and the ferrocene dissolved. my question is what has actually happened?

[Hunter2]

Well probably you destroyed it and oxdised the iron to iron-III-nitrate.  Probably also a nitration on the benzene rings took place.

[gkasparis]

you cant say i destroyed it  that was the aim to check its reactivity with the acid. i knew the two possibilites, of the ferrocenium ion and the nitration. how can i distiguish between the two?

[Hunter2]

If you can seperate organic and aqueaous phase, then you can check with thiocyanate if iron-III is formed => red colour. For the organic stuff you need maybe more high advanced analytic.

[gkasparis]

i dont have the sample anymore. so i have to suggest both possibilities since i cannot distiguish?
or is one far more favourable than the other?

[Arkcon]

For the organic stuff you need maybe more high advanced analytic.

Or just dry it and ignite it.  If you don't have fingers afterward, you've nitrated the organic.


*Note*  The assay mentioned above is in no way meant to be absolutely quantitative, or actually possible, or you know, even remotely safe.  More a joke, really.  However, generally, redox reactions to the ferrocenium ion are conducted more gently than by concentrated nitric acid:  http://en.wikipedia.org/wiki/Ferrocene#Redox_chemistry

[Hunter2]

If you don't have fingers afterward, you've nitrated the organic.

 Very funny. But I dont think it will blow up. Nitro-benzene will burn safely still.

[Arkcon]

If you don't have fingers afterward, you've nitrated the organic.

 Very funny. But I dont think it will blow up. Nitro-benzene will burn safely still.

I wasn't really sure, so I did throw in the caveat:

*Note*  The assay mentioned above is in no way meant to be absolutely quantitative,

 

[Hunter2]

Oh, I figured out I am wrong. Ferrocene is made by cyclopentadien not benzene. So the oxidation will probably not get nitro substitutes  probably oxidiing to carbonic acid or ketones.