Question:medium

The correct order of acidity of the following compounds is

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Electron-donating groups decrease acidity of phenols, while electron-withdrawing groups increase acidity.
Updated On: Jun 15, 2026
  • \(III\gt II\gt I\)
  • \(II\gt III\gt I\)
  • \(I\gt II\gt III\)
  • \(III\gt I\gt II\)
Show Solution

The Correct Option is C

Solution and Explanation

Step 1: Link acidity to phenoxide stability.
A phenol is more acidic when the phenoxide ion left behind after losing a proton is more stable. Electron donating groups push electron density into the ring, destabilise that negative ion, and lower acidity.
Step 2: Analyse compound I (phenol).
Plain phenol has no donating substituent, so its phenoxide is the least destabilised among the three, making it the most acidic.
Step 3: Analyse compound II (p-cresol).
The methyl group donates electrons by a weak $+I$ effect, slightly destabilising the phenoxide and making it less acidic than phenol.
Step 4: Analyse compound III (p-methoxyphenol).
The methoxy group donates electrons strongly by resonance ($+M$), which destabilises the phenoxide the most and makes this the least acidic.
Step 5: Rank the three.
Combining these, acidity follows $I \gt II \gt III$.
Step 6: Choose the option.
This ordering is option (3). \[ \boxed{I \gt II \gt III} \]
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