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JEE Main · 2013 · 07 Apr 2013 · Offline · Alcohols Phenols and Ethers

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Arrange the following compounds in order of decreasing acidity:
Structure I
I
Structure II
II
Structure III
III
Structure IV
IV
  1. (A)I > II > III > IV
  2. (B)III > I > II > IV✓ Correct
  3. (C)IV > III > I > II
  4. (D)II > IV > I > III

Answer: (B)

Solution

Acidity of a phenol rises when the ring carries electron-withdrawing groups, which steady the phenoxide, and falls with electron-donating groups. The nitro-substituted phenol (III) is the most acidic; the chloro compound (I), weakly electron-withdrawing, comes next; then the methyl (II) and the methoxy (IV), both electron-donating, are least acidic. The order of decreasing acidity is III I II IV.

JEE Main · 2013 · 07 Apr 2013 · Offline · Single correct option

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