In comparing the acidic strength of p-nitrophenol and m-nitrophenol, which of the following statemen — GOC 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.
💬Ask on WhatsApp →
Still have doubts about this question?
Send it to our AI chemistry tutor on WhatsApp — gets answered in minutes