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I was doing an experiment in lab and found that about one-third of p-nitrophenol dissolved in $\ce{NaHCO3}$ solution with liberation of $\ce{CO2}$ in small amount. This is contradictory to what most textbooks say. I was surprised as p-nitrophenol is less acidic than carbonic acid yet it gave positive $\ce{NaHCO3}$ test.

Can anyone give any possible explanation? I thought that one reason maybe that since their $\mathrm{pK}_\mathrm a$ differ by about $1$, the reaction maybe in equilibrium to a significant extent, but this kind of thing isn't mentioned anywhere.

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  • $\begingroup$ Perhaps the textbook is wrong. Seeing is believing. :) $\endgroup$ Commented May 15, 2017 at 7:00
  • $\begingroup$ Experimental details matter here, but are lacking from your question. $\endgroup$
    – Zhe
    Commented Feb 22, 2018 at 15:10

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