MolSynapsequestion bank
MolSynapse / Question bank / Stereoisomerism / Chirality, enantiomers and R/S configuration
JEE Advanced levelSingle correct optionDifficulty 3 of 3st180

(4aR,8aS)-Octahydronaphthalen-2(1H)-one (2-decalone, numbered C1 to C8 with ring-fusion carbons 4a and 8a, C=O at C2) is given. Using CIP rules, which statement is correct?

  1. AThe ring fusion is trans, and the enantiomer is (4aS,8aR)
  2. BThe ring fusion is cis, and the compound is meso because 4aR and 8aS cancel
  3. CThe ring fusion is trans, and the compound is achiral
  4. DThe ring fusion is cis, and the enantiomer is (4aS,8aR)

Answer: D

At C8a the priorities are C4a > C1 (leads to C=O) > C8 > H, and at C4a they are C8a > C4 > C5 > H. Working both centres through for the two ring fusions (with an explicit CIP check) gives like descriptors (4aR,8aR or 4aS,8aS) for trans-fusion and unlike descriptors (4aR,8aS or 4aS,8aR) for cis-fusion. So the given compound is cis-fused. It has no internal mirror plane because C1 and C4 are inequivalent (the C=O is at C2), so it is chiral and its enantiomer is (4aS,8aR).
Practice Stereoisomerism More on Chirality, enantiomers and R/S configuration

More questions on Chirality, enantiomers and R/S configuration