# How does the relative acidity of 2,3-dinitrophenol compare to that of 2,4-dinitrophenol?

I am assuming that the -I inductive effect in 2,3-dinitrophenol is stronger than in 2,4-dinitrophenol since it operates through less bonds, therefore on inductive grounds it should have a lower $$\mathrm{p}K_\mathrm{a}$$?

However it's unclear to me whether there are any differences in π-resonance effects. Any help?

• Can you draw resonance structures for the conjugate base? – orthocresol Nov 25 '19 at 19:09
• @orthocresol I got 3 resonance forms for the conjugate bases of each. Is this correct? – Anne Nov 25 '19 at 19:19
• You seems to forgot to include nitro groups. Try again and see. – Mathew Mahindaratne Nov 25 '19 at 20:02
• @MathewMahindaratne the conjugate base of 2,4-nitrophenol would be more stable and therefore it would be more acidic. Thank you for your guidance. – Anne Nov 25 '19 at 20:59
• You got it! :-) – Mathew Mahindaratne Nov 25 '19 at 21:32