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JEE Advanced 2019 Paper 1 · Chemistry · General Organic Chemistry and Isomerism · hard

The number of stereoisomers (counting enantiomers separately) of the compound CH3CH=CH-CH(OH)-CH=CH-CH3 (hepta-2,5-dien-4-ol) is

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The number of stereoisomers (counting enantiomers separately) of the compound CH3CH=CH−CH(OH)−CH=CH−CH3\mathrm{CH_3CH{=}CH{-}CH(OH){-}CH{=}CH{-}CH_3} (hepta-2,5-dien-4-ol) is
  1. A. 3
  2. B. 6
  3. C. 4
  4. D. 8
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Answer: (C) 4

There are two stereogenic double bonds (C2=C3 and C5=C6) and a carbinol carbon C4. Treat the double-bond geometries first. For (E,E)(E,E) and (Z,Z)(Z,Z) the two groups on C4 are identical in constitution and configuration, so C4 is not a stereocentre and each gives one achiral (meso-like) compound. For (E,Z)(E,Z) the two alkenyl arms differ in configuration, so C4 carries four different groups and is a true stereocentre; the (E,Z)(E,Z) and (Z,E)(Z,E) descriptions are the same compound with the numbering reversed, so we get only one constitution-geometry pair but two enantiomers, (4R)(4R) and (4S)(4S). Total =1+1+2=4=1+1+2=4. The naive 23=82^3=8 overcounts, and 3 forgets the enantiomeric pair.
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