I know if the $\ce{-NO2}$ group be added at the ortho position with respect to the $\ce{-OH}$, hydrogen bonding between the hydroxyl and nitro groups would lead to stability.

But would that product be major considering steric factors?

  • 4
    $\begingroup$ Nitro groups really "don't like" to be next to each other - that leaves one position. $\endgroup$
    – Mithoron
    Jul 14, 2022 at 14:41
  • 1
    $\begingroup$ A Chem. Absts. search claims nitration para to OH. The patent was TL:DR. No structures. For what it is worth. $\endgroup$
    – user55119
    Jul 14, 2022 at 19:28

1 Answer 1


Nitration of phenol with concentrated nitric acid gives 2,4,6-trinitrophenol . So, it is quite possible here that the corresponding substituted trinitrophenol may form in the reaction. But you have also added concentrated sulphuric acid so it may cause some other product to form.

Generally electrophilic aromatic substitution of phenol gives para product in slightly higher amount than ortho product due to inductive effect of oxygen. However in case of nitration, ortho product becomes higher than para product due to intramolecular hydrogen bond formation. So I think that it should be major product in your reaction also

  • $\begingroup$ Can you cite a source for the nitration of phenol by concentrated nitric acid which gives benzoquinone as major product. Because I couldn't able to find it in the internet. $\endgroup$
    – Infinite
    Jul 15, 2022 at 14:00
  • $\begingroup$ conc. $\ce{H_2SO_4}$ and conc. $\ce{HNO_3}$ form $\ce{NO^+}$, thus hydrogen bonding may not be the deciding factor for the kinetic pathway. $\endgroup$
    – ananta
    Jul 15, 2022 at 19:32
  • $\begingroup$ Why was this even upvoted? Nitro group is in meta - not considering this makes any answer a waste of time. Not to mention steric effects are way more important than tenuous h-bond. $\endgroup$
    – Mithoron
    Jul 15, 2022 at 23:12
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    $\begingroup$ @ananta how is $\ce{NO^+}$ formed? When I woke up this morning I was sure it was $\ce{NO2^+}$. $\endgroup$ Dec 12, 2022 at 16:15
  • $\begingroup$ must have been a typo, you are right $\text{NO}_{\text{2}}^+$ is formed, we are substituting the $\ce{H}$ with $\ce{NO2}$ groups $\endgroup$
    – ananta
    Dec 12, 2022 at 22:16

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