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JEE Main levelSingle correct optionDifficulty 2 of 3g3229

The secondary carbocation shown undergoes a single 1,2-hydride shift to give a cation stabilised by the aromatic ring. Which structure shown is the cation formed?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: B

The cation shown is the 1-phenylpropan-2-yl cation. A hydride moves from the benzylic CH to the adjacent cationic carbon, which places the charge on the benzylic carbon. The product is the 1-phenylpropyl cation, a benzylic cation stabilised by resonance with the ring, much more stable than the unconjugated secondary cation.
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