Substitution Patterns in Aromatic Compounds

Very Hard Organic Chemistry Aromatic Compounds

Aromatic compounds are characterized by their stability and unique reactivity due to the delocalization of electrons. Consider the following compound, which is known for its use as a dye: 2,4-dinitrophenol (C6H4N2O5). This molecule features two nitro (-NO2) substituents on the aromatic ring, which can significantly influence its chemical behavior.

When analyzing 2,4-dinitrophenol, its suitability for various reactions, especially electrophilic aromatic substitution, is of interest. The positions of electron-withdrawing and electron-donating groups on the ring have substantial effects on reaction rates and orientations. Based on your understanding of resonance structures and substitution patterns in aromatic compounds, which of the following statements about the orientation of substitution reactions in 2,4-dinitrophenol is correct?

Substitution will predominantly occur at the 5-position due to the electron-withdrawing effect of the nitro groups.

Substitution will predominantly occur at the 1-position as the nitro groups have a meta-directing effect.

Substitution is equally likely at the 2- and 4-positions as both positions are ortho to a nitro group.

Substitution will predominantly occur at the 3-position, as nitro groups activate meta substitution.

Hint

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