MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms IV: Elimination / E2 anti-periplanar requirement on drawn ring systems
JEE Main levelSingle correct optionDifficulty 2 of 3o4245

The meso compound shown loses one molecule of HBr (anti E2) on treatment with a strong base. Which structure is the 1-bromo-1,2-diphenylethene formed?

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

Answer: D

The compound is meso-1,2-dibromo-1,2-diphenylethane. With H on one carbon anti to Br on the other, the two phenyl groups end up cis, so the bromine on the remaining carbon is trans to the phenyl on the other carbon, which is the (E)-alkene. The chiral (R,R) or (S,S) dibromide would give the (Z)-alkene. Diphenylacetylene needs a second elimination and stilbene would need loss of Br2.
Practice Organic Reaction Mechanisms IV: Elimination More on E2 anti-periplanar requirement on drawn ring systems

More questions on E2 anti-periplanar requirement on drawn ring systems