JEE Challenger
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Total Number of Optically Active Stereoisomers for Compound X

For the given compound X\mathbf{X}, determine the total number of optically active stereoisomers.

Question Diagram 1
Official Numerical Answer7

Step-by-Step Solution

To determine the total number of optically active stereoisomers for compound X\mathbf{X}, we analyze the fixed and variable stereogenic units present in its structure.

1. Analysis of Stereogenic Units

  • Fixed stereocenters and double bonds (represented by solid wedges/thick bonds):

    1. The two −OH-OH groups on the cyclopentane ring are fixed in their configurations (both represented by solid wedges).
    2. The upper side chain has:
      • A fixed double bond geometry (EE-configuration / trans).
      • A fixed stereocenter at the carbon attached to the upper −OH-OH group (solid wedge).
  • Variable stereogenic units (represented by wavy lines):

    1. The stereocenter at the cyclopentane ring carbon attached to the lower side chain (2 choices: RR or SS).
    2. The double bond geometry in the lower side chain (2 choices: EE or ZZ).
    3. The stereocenter at the lower side chain carbon attached to the −OH-OH group (2 choices: RR or SS).

2. Calculation of Total Stereoisomers

Since there are 33 independent variable stereogenic units, the total number of stereoisomers generated is: Ntotal=23=8N_{\text{total}} = 2^3 = 8

3. Determination of Optically Active Stereoisomers

The cyclopentane core containing the two identical ring −OH-OH groups with fixed, identical configurations possesses a potential internal plane of symmetry (σ\sigma) passing through the isolated ring CH2CH_2 group and bisecting the bond between the two chain-bearing ring carbons.

  • Meso Compound (Optically Inactive): Out of the 88 possible configurations for the lower chain, exactly 11 configuration matches the stereochemistry of the upper chain such that the molecule possesses a plane of symmetry. This single stereoisomer is a meso compound and is optically inactive.

  • Optically Active Stereoisomers: The remaining stereoisomers lack any plane of symmetry or inversion center, making them chiral and optically active.

Total number of optically active stereoisomers=Ntotal−Nmeso=8−1=7\text{Total number of optically active stereoisomers} = N_{\text{total}} - N_{\text{meso}} = 8 - 1 = 7