KCET · Chemistry · Alcohols Phenols and Ethers
Which of the following is strongly acidic?
- A Phenol
- B o-cresol
- C p-nitrophenol
- D \(p\)-cresol
Answer & Solution
Correct Answer
(C) p-nitrophenol
Step-by-step Solution
Detailed explanation
The acidity of phenols is due to the greater resonance stabilization of the phenoxide ion relative to phenol. Therefore, electron withdrawing groups (EWG) like - \(\mathrm{NO}_{2}\) which stabilize the phenoxide ion more by dispersing the negative charge will tend to increase the acidity of phenols.
On the other hand, electron donating groups (EDG) like-alkyl group destabilize the phenoxide ion by intensifying the negative charge relative to phenol tend to decrease the acidic strength of phenols.
As methyl group has \(+1\) effect and it is stronger at o-position than at p-position, (+ / effect decreases with distance) o-cresol is a weaker acid than \(p\)-cresol.
Thus, the order of acidic strength.
\(p\) - nitrophenol \(>\) phenol \(>p\) - cresol \(>0\)-cresol
On the other hand, electron donating groups (EDG) like-alkyl group destabilize the phenoxide ion by intensifying the negative charge relative to phenol tend to decrease the acidic strength of phenols.
As methyl group has \(+1\) effect and it is stronger at o-position than at p-position, (+ / effect decreases with distance) o-cresol is a weaker acid than \(p\)-cresol.
Thus, the order of acidic strength.
\(p\) - nitrophenol \(>\) phenol \(>p\) - cresol \(>0\)-cresol
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