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JEE Main 2025 · Chemistry · General Organic Chemistry and Isomerism · hard

The total number of stereoisomers possible for hex-3-ene-2,5-diol, CH3CH(OH)CH=CHCH(OH)CH3, is

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The total number of stereoisomers possible for hex-3-ene-2,5-diol, CH3CH(OH)CH=CHCH(OH)CH3\mathrm{CH_3CH(OH)CH{=}CHCH(OH)CH_3}, is
  1. A. 44
  2. B. 88
  3. C. 33
  4. D. 66
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Answer: (D) 66

The molecule has a double bond (E/Z) and two identical stereocentres (C2 and C5), so it is symmetric. For each geometry the centre configurations are (R,R)(R,R), (S,S)(S,S) and (R,S)(R,S); the last is a meso compound because the two halves are mirror related, and (S,R)(S,R) is identical to it. So each geometry gives 33 stereoisomers. Total =2×3=6=2\times3=6 (not 23=82^3=8, which ignores the symmetry).
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