Blind Angel
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De-Nitratation?
I rode the post on the nitratation of the acetone to yield nitro organic peroxide, but here's my question if you can convert a Methyl group to a
Nitro group the inverse is surely possible but how? (maybe this question is easy, my knowledge don't tell me)
And also, when working with benzene substance, how do you know whic C atom will bound with what (like Trinitrophenol, which as an hydroxy group linked
to one of the C and three nitro in "Y" to other). i've heard about ortho, metha and para, which does what and how do you know which of
them a substance is?
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My PGP Key Fingerprint: D4EA A609 55E4 7ADD 8529 359D D6E2 33F6 4C76 78ED |
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BASF
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The benzene ring is, as opposed to non-aromatic substances not able to be reacted with a nucleophil (species with high electronegativity that attacks
less electonegative species, which are in turn called electrophiles) like NO2-, because it acts like a nucleophil itself.
That´s why you can attack the benzene ring predominantly with positively polarized or charged molecules only.
In the case of the nitration of phenol, you will get an ortho(position next to the OH-group) and para-nitration(the opposite side on the ring),
because the OH- group activates the ring, which means it donates electron density to the ring by resonance.
OH- and NH2- are normally more electronegative than carbon and would be expected to desactivate the ring, which would lead to a meta-nitration(this is
the 3rd carbon counted left or right from the first substituent), but they can undergo resonance with the ring.
Using several resonance formulas you can explain the ortho-meta-para-behaviour of aromatic systems, but this is a little bit difficult to explain only
in words...
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Blind Angel
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I see that my theory can't work... here's what i was thinking of:
Take Acetaminophene, nitrate it like you would nitrate DNP (by my though it would be an Ortho nitratation since the para is already took by the
NHCOCH<sub>3</sub> [ketone?]) you would now have 2,6-nitro-N-acetyl-4-aminophenol (apologize my nomenclature), no? Then you replace the
nitro group using methoxy one, this would yield 2,6-dimethoxyacetyl-4-aminophenol (i know this would need a lot of energy). The side product of this
reaction, if using methanol, would be HNO<sub>3</sub>.
With the above substance you replace the hydroxy groupe with another methoxy one. You now have 1,2,6-trimethoxyacetyl-4-amine, which strangely look
like a Mescaline molecule 
P.S. That this would work would have surprised me a lot, but it cost nothing trying and learning
/}/_//|//) /-\\/|//¬/=/_
My PGP Key Fingerprint: D4EA A609 55E4 7ADD 8529 359D D6E2 33F6 4C76 78ED |
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