Q4 / 200 · WBJEE 2013 · Chemistry

(+)-2-chloro-2-phenylethane in toluene racemises slowly in the presence of small amount of $\mathrm{SbCl}_{5},$ due to the formation of

  • A
    carbanion
  • B
    carbene
  • C
    free-radical
  • Correct answer
    D
    carbocation

Solution

A planar carbocation is generated when $\mathrm{SbCl}_{5}$ remove $\mathrm{Cl}^{-}$ from the substrate. This carbocation is subsequently attacked by $\mathrm{Cl}^{-}$ (nucleophile) from both the sides (j.e. from top and bottom) to produce a racemic mixture.

Hence, the correct answer is option: 'D'.

More General Organic Chemistry Questions