Which one is the most acidic compound ?
Which one is the most acidic compound ?

1. [structure: phenol]
2. [structure: 4-nitrophenol]
3. [structure: 2,4,6-trinitrophenol]
4. [structure: 4-methylphenol]
Which one is the most acidic compound ?

1. [structure: phenol]
2. [structure: 4-nitrophenol]
3. [structure: 2,4,6-trinitrophenol]
4. [structure: 4-methylphenol]
Best answer
Answer: 3. [structure: 2,4,6-trinitrophenol]
Key idea: electron-withdrawing groups stabilise the phenoxide ion and increase acidity.
2,4,6-Trinitrophenol (picric acid) has three \(\mathrm{-NO_2}\) groups at o,p positions, which strongly delocalise the negative charge (-R, -I). 4-Nitrophenol is less acidic, phenol less still, and 4-methylphenol (electron-donating methyl) is the least acidic. So picric acid is most acidic.
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