MolSynapsequestion bank
MolSynapse / Question bank / Stereoisomerism / Fischer, Newman and sawhorse projections
JEE Advanced levelSingle correct optionDifficulty 3 of 3st106

Use these gauche interaction energies (dihedral only, no other terms): Br/Br , Br/ , / kJ/mol; any interaction involving H is zero. The anti-Br staggered conformer of meso-2,3-dibromobutane has front carbon Br at 12, at 4, H at 8 o'clock, and rear carbon Br at 6, at 10, H at 2 o'clock. Rotating the rear carbon by gives the two gauche-Br staggered conformers. What is the energy of a gauche-Br conformer relative to the anti-Br conformer?

  1. A kJ/mol
  2. B kJ/mol
  3. C kJ/mol
  4. D kJ/mol

Answer: B

In the anti conformer the gauche pairs are front Br/rear (10 o'clock) and front /rear Br (6 o'clock), giving kJ/mol. In each gauche-Br conformer the gauche pairs are Br/Br (), Br/ () and / (), totalling kJ/mol. The relative energy is kJ/mol.
Practice Stereoisomerism More on Fischer, Newman and sawhorse projections

More questions on Fischer, Newman and sawhorse projections