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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4070

(1S,2S)-1-Bromo-1,2-diphenylpropane is treated with /ethanol. The only beta hydrogen is on C-2, and the reaction is a concerted anti E2 elimination. The product is

  1. A(Z)-1,2-diphenylprop-1-ene (the two phenyl groups cis)
  2. B2,3-diphenylprop-1-ene
  3. Ca 1:1 mixture of E and Z isomers
  4. D(E)-1,2-diphenylprop-1-ene (the two phenyl groups trans)

Answer: A

In the conformation with H on C-2 anti-periplanar to Br on C-1, the two phenyl groups lie 60 degrees apart in the Newman projection, so after elimination they are cis. A three-dimensional model of the (1S,2S) isomer confirms this, giving the Z alkene, and the (1S,2R) diastereomer would give the E alkene instead. Anti elimination is stereospecific, so one isomer is formed.
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