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JEE Advanced 2020 Paper 2 · Chemistry · General Organic Chemistry and Isomerism · medium

Number of stereoisomers (including enantiomers and meso forms) is/are correct?

One or more options correct

Which of the following statements about the number of stereoisomers (including enantiomers and meso forms) is/are correct?
  1. A. Butane-2,3-diol, CH3CH(OH)CH(OH)CH3\mathrm{CH_3CH(OH)CH(OH)CH_3}, has three stereoisomers.
  2. B. 1,3-Dimethylcyclohexane has three stereoisomers.
  3. C. 1,4-Dimethylcyclohexane has three stereoisomers.
  4. D. Hexa-2,4-diene, CH3CH=CH−CH=CH−CH3\mathrm{CH_3CH{=}CH{-}CH{=}CH{-}CH_3}, has three stereoisomers.
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Answer: A, B, D

Option A: butane-2,3-diol has two like stereocentres in a symmetric skeleton, giving the (R,R)(R,R) and (S,S)(S,S) enantiomeric pair plus the achiral meso (R,S)(R,S) form, which makes three, so A is correct. Option B: 1,3-dimethylcyclohexane has two stereocentres (C1\mathrm{C_1} and C3\mathrm{C_3}); the cis isomer has an internal mirror plane and is meso, while the trans isomer is chiral and exists as a pair of enantiomers, giving three, so B is correct. Option C: in the 1,4-isomer both substituted carbons lie on a mirror plane, so there are only cis and trans, both achiral, giving two, so C is wrong. Option D: the symmetrical diene has (E,E)(E,E), (Z,Z)(Z,Z) and (E,Z)(E,Z) forms, and the (Z,E)(Z,E) form is identical to (E,Z)(E,Z), giving three, so D is correct.
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