GOC and Organic Chemistry BasicshardMCQ SINGLE

In comparing the acidic strength of p-nitrophenol and m-nitrophenol, which of the following statemenGOC and Organic Chemistry Basics Chemistry Question

Question

In comparing the acidic strength of p-nitrophenol and m-nitrophenol, which of the following statements correctly explains why p-nitrophenol is significantly more acidic?

Answer: B

💡 Solution & Explanation

The mesomeric effect only effectively operates at the ortho and para positions due to the pattern of $\pi$ electron delocalization. In p-nitrophenol, the electron-withdrawing $-M$ effect of the $-NO_2$ group can directly stabilize the negative charge on the phenoxide oxygen via extended resonance. In m-nitrophenol, only the weaker $-I$ effect stabilizes the anion, making it a weaker acid.

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