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JEE Main 2023 · Chemistry · General Organic Chemistry and Isomerism · hard

The total number of stereoisomers (including geometrical isomers) possible for CH3CH(OH)CH=CHCH(OH)CH3 is

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The total number of stereoisomers (including geometrical isomers) possible for CH3CH(OH)CH=CHCH(OH)CH3\mathrm{CH_3CH(OH)CH=CHCH(OH)CH_3} is
  1. A. 66
  2. B. 88
  3. C. 44
  4. D. 33
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Answer: (A) 66

The molecule has a C=C\mathrm{C=C} (E/Z possible) and two identical stereocentres (C2 and C5), so it is symmetrical. For each geometry the centres can be (R,R)(R,R), (S,S)(S,S) (a pair of enantiomers) or (R,S)(R,S) (meso, identical to (S,R)(S,R)). That gives 33 isomers for EE and 33 for ZZ, so 66 in all. The formula 23=82^3=8 overcounts because the molecule has a plane or centre of symmetry in the (R,S)(R,S) forms.
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