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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3st220

Which statements about decalin (bicyclo[4.4.0]decane) are correct?

  1. AIn cis-decalin the two bridgehead hydrogens are anti-periplanar
  2. Btrans-Decalin cannot undergo ring flipping, because a flip would require the two ring-fusion bonds to become diaxial
  3. CIn trans-decalin the two bridgehead hydrogens are anti-periplanar (both axial with respect to each ring)
  4. DDecalin has exactly two configurational stereoisomers, cis and trans, and both are achiral (conformational averaging taken into account)

Answer: B, C, D

In trans-decalin each ring-fusion bond is equatorial to the other ring; a chair flip would make them both axial, which cannot span a trans fusion, so the molecule is locked and the two bridgehead H atoms are both axial and anti (180). cis-Decalin ring-flips freely and its bridgehead H atoms are gauche (about 60), so the first statement is false. Only cis and trans exist as configurations; trans has an inversion centre and cis has a time-averaged mirror plane (its ring flip interconverts two enantiomeric chairs), so both are achiral.
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