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JEE Advanced levelSingle correct optionDifficulty 3 of 3g1207

Cyclohepta-1,3,5-triene reacts with triphenylmethyl cation, , by transfer of a hydride ion from its group to give and triphenylmethane. The main reason this hydride transfer is favourable is that:

  1. A is cyclic, planar and fully conjugated with 6 pi electrons, i.e. aromatic
  2. B has 8 pi electrons and is therefore antiaromatic and stable
  3. C is a tertiary carbocation with many alpha hydrogens
  4. DThe C-H bond of the group of the triene is unusually weak because it is sp hybridised

Answer: A

Loss of hydride from the sp3 CH2 of cycloheptatriene leaves a seven-carbon ring with seven p orbitals and 6 pi electrons (three double bonds), the tropylium cation. It satisfies Huckel's 4n+2 rule (n = 1), so the large gain in aromatic stabilisation drives the hydride transfer.
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