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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o4107

meso-1,2-Dibromo-1,2-diphenylethane and its racemic diastereomer (1R,2R / 1S,2S) are each treated with one equivalent of (anti E2 giving 1-bromo-1,2-diphenylethene). Select all correct statements.

  1. AThe meso isomer gives (E)-1-bromo-1,2-diphenylethene, in which the two phenyl groups are cis.
  2. BThe racemic (1R,2R / 1S,2S) isomer gives (Z)-1-bromo-1,2-diphenylethene, in which the two phenyl groups are trans.
  3. CThe meso isomer gives (Z)-1-bromo-1,2-diphenylethene.
  4. DBoth diastereomers give the same alkene because the benzylic hydrogens are acidic and the geometry is scrambled.

Answer: A, B

In an anti E2 the H and Br must lie 180 degrees apart. For the meso isomer, placing H anti to Br leaves the two phenyl groups 60 degrees apart, so they end up cis (Br is then trans to the phenyl on the other carbon, which is E). For the racemic isomer the phenyl groups end up trans and Br cis to the other phenyl, which is Z. The reaction is stereospecific, not scrambled.
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