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JEE Advanced levelSingle correct optionDifficulty 3 of 3g1174

Consider the acidity of the benzylic hydrogens in I 4-nitrotoluene, II toluene and III 4-methoxytoluene. The correct order of decreasing acidity is:

  1. AI > II > III
  2. BIII > II > I
  3. CI > III > II
  4. DII > I > III

Answer: A

The acidity depends on the stability of the benzyl anion, with charge at ortho and para carbons. A para nitro group stabilises it by -M and -I, increasing acidity. A para methoxy group is a net donor (+M) towards the anionic centre and destabilises it. So I > II > III.
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