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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro055

Consider SN1 hydrolysis in aqueous ethanol of (I) , (II) 4-methoxybenzyl chloride and (III) 4-nitrobenzyl chloride. The correct order of rate is

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

Answer: D

The rate depends on the stability of the benzyl cation. The p-OCH3 group stabilises it strongly by resonance (II fastest), the p-NO2 group destabilises it (III slowest), with the parent benzyl in between.
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