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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g1168

Which of the following statements are correct?

  1. AThe 4-methoxybenzyl cation is more stable than the 3-methoxybenzyl cation
  2. BThe 4-nitrobenzyl cation is less stable than the benzyl cation
  3. CThe 3-nitrobenzyl cation is more stable than the 4-nitrobenzyl cation
  4. DThe 4-methoxybenzyl cation is less stable than the benzyl cation because oxygen is electronegative (-I)

Answer: A, B, C

A para methoxy group donates by +M directly to the charged ring positions, whereas at the meta position only its -I effect operates, so 4-OMe > 3-OMe and 4-OMe > benzyl. A nitro group destabilises the cation. At the para position the nitro group sits on a carbon that bears positive charge in a resonance structure (-M and -I), so 4-nitro is worse than 3-nitro (only -I) and worse than benzyl.
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