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JEE Advanced 2024 Paper 1 · Chemistry · General Organic Chemistry and Isomerism · hard

The total number of stereoisomers (counting each enantiomer separately) possible for the compound CH3CH=CH-CH(OH)-CH=CHCH3 is

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The total number of stereoisomers (counting each enantiomer separately) possible for the compound CH3CH=CH−CH(OH)−CH=CHCH3\mathrm{CH_3CH{=}CH{-}CH(OH){-}CH{=}CHCH_3} is
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Answer: 4

There are two stereogenic double bonds and one carbinol carbon. The carbinol carbon bears H, OH and the two CH=CHCH3\mathrm{CH{=}CHCH_3} arms. It is a stereocentre only when the two arms differ, i.e. when the double-bond geometries are E,ZE,Z. Cases: (E,E) has identical arms, so no stereocentre and the molecule is achiral: 1 isomer. (Z,Z): likewise 1 isomer. (E,Z): the carbinol carbon is a true stereocentre, giving two enantiomers (R and S): 2 isomers. A combinatorial enumeration with the symmetry equivalence (e1,e2,s)∼(e2,e1,−s)(e_1,e_2,s)\sim(e_2,e_1,-s) confirms 4 distinct stereoisomers in total. Answer: 4.
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