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JEE Main 2020 · Chemistry · General Organic Chemistry and Isomerism · medium

The total number of stereoisomers (geometrical plus optical) possible for CH3-CH=CH-CH(OH)-CH(Cl)-CH3 is

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The total number of stereoisomers (geometrical plus optical) possible for CH3−CH=CH−CH(OH)−CH(Cl)−CH3\mathrm{CH_3-CH=CH-CH(OH)-CH(Cl)-CH_3} is
  1. A. 44
  2. B. 66
  3. C. 88
  4. D. 1212
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Answer: (C) 88

The double bond C2=C3\mathrm{C_2=C_3} carries different groups on each carbon, so it shows E/ZE/Z isomerism (2). C4\mathrm{C_4} (H, OH, propenyl, CHClCH3\mathrm{CHClCH_3}) and C5\mathrm{C_5} (H, Cl, CH3\mathrm{CH_3}, CH(OH)R\mathrm{CH(OH)R}) are both stereocentres and the molecule has no symmetry, giving 222^2 combinations. Total =2×2×2=8=2\times2\times2=8.
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