Maybe i think 5 position of phen was nitration by HNO3 and H2SO4 and Br- in NaBr reducted nitro group in phen. But, how can phendione be produced?
Jae Jun Lee:
The electrophillic substitution reactions such as nitration on the aromatic hydrocarbons phenanthrene and1,10- phenanthroline are generally difficult/complicated. That is due to the higher reactivity of the functional unit (that may not be real part of aromatic system as shown in attached file) toward addition reactions. Due to its typical reactivity, this structural unit generally behaves like alkene in few reactions and is more prone to give addition reactions rather than substitutions. In your experiment, you have used two oxidizing agents such as nitric acid acid and sulphuric acid. There may be many complicated processes involving in the oxidation. The most reasonable is given in the attachment.
Many things can happen in this condition. You have HNO3 as oxid-reagent and Br- as red-reagent! To find the answer for a Oxi-red reaction is very diffucult, i think you should accept the result of the reaction and don't try to find out the mechanism!
Jae Jun Lee:
The electrophillic substitution reactions such as nitration on the aromatic hydrocarbons phenanthrene and1,10- phenanthroline are generally difficult/complicated. That is due to the higher reactivity of the functional unit (that may not be real part of aromatic system as shown in attached file) toward addition reactions. Due to its typical reactivity, this structural unit generally behaves like alkene in few reactions and is more prone to give addition reactions rather than substitutions. In your experiment, you have used two oxidizing agents such as nitric acid acid and sulphuric acid. There may be many complicated processes involving in the oxidation. The most reasonable is given in the attachment.
Thank you, Dr Kumar. Good explianation of the attachment.
Do you know what happen in the last step of the reaction in your attachment? , which is the two oxygens are generated in phen.
Does the other oxygen come from the nitric acid?
Sushil. really you have good knowledge. Please answer my call once on skype.
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