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JEE Main levelSingle correct optionDifficulty 2 of 3g3026

1-Chlorobicyclo[2.2.1]heptane (chlorine on the bridgehead carbon) is almost inert in solvolysis because:

  1. Athe cation formed would be antiaromatic
  2. Ba bridgehead carbon is primary
  3. Cchloride is not a leaving group in bicyclic compounds
  4. Dthe bridgehead carbocation cannot become planar, so it cannot be stabilised

Answer: D

A carbocation needs a planar centre. In the rigid bicyclic skeleton the bridgehead carbon cannot flatten, so ionisation is extremely slow even though the carbon is bonded to three other carbons.
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