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 Two possibilities of products if oxidation occurs before nitration and vice-versa

Which of the cases is possible or both or none?

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  • $\begingroup$ Would definitely oxidise. Protect the amine but reacting with acyl chloride to make abide to make the aromatic ring less activated. $\endgroup$ – RobChem Dec 26 '16 at 15:21
  • $\begingroup$ None, oxidative oligomerisation happens. $\endgroup$ – Mithoron Dec 26 '16 at 16:31
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Concentrated $\ce{HNO3}$ is ‘only’ around $70~\%$. To add a nitro functionality by electrophilic aromatic substitution, typically the $\ce{NO2+}$ cation is required which is formed only by strong dehydrating agents such as sulfuric acid:

$$\ce{O2N-OH <<=>[\ce{H2SO4}][-\ce{HSO4-}] O2N-OH2+ ->[][-\ce{H2O}] O=\overset{+}{N}=O}\tag{1}$$

Concentrated nitric acid is not strong enough to dehydrate iself. Thus, nitration will typically not be observed.

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  • $\begingroup$ Not really, nitration doesn't even need any acid in some variants. $\endgroup$ – Mithoron Dec 26 '16 at 16:33
  • $\begingroup$ So oxidation would occur first? @Jan,Melanie Shebel $\endgroup$ – Swastik Apr 10 '17 at 7:49

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