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JEE Advanced 2021 Paper 1 · Chemistry · General Organic Chemistry and Isomerism · hard

(s) about the number of stereoisomers (including optical isomers) or optical activity.

One or more options correct

Select the correct statement(s) about the number of stereoisomers (including optical isomers) or optical activity.
  1. A. 3-Methylpent-2-ene exists as exactly two stereoisomers
  2. B. 1,2-Dimethylcyclopropane exists as exactly two stereoisomers
  3. C. Penta-2,3-diene (CH3CH=C=CHCH3\mathrm{CH_3CH{=}C{=}CHCH_3}) is optically active
  4. D. 1,3-Dimethylcyclobutane exists as exactly three stereoisomers
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Answer: A, C

(A) is correct: CH3CH=C(CH3)CH2CH3\mathrm{CH_3CH{=}C(CH_3)CH_2CH_3} has no stereocentre and each alkene carbon carries two different groups, so only the EE and ZZ isomers exist. (B) is wrong: 1,2-dimethylcyclopropane has a cis form (meso, with a plane of symmetry) and a trans form (chiral, existing as two enantiomers), so exactly three stereoisomers exist, not two. (C) is correct: penta-2,3-diene has the two terminal carbons each carrying H\mathrm{H} and CH3\mathrm{CH_3} in perpendicular planes, which gives axial chirality (a three-dimensional model is non-superposable on its mirror image). (D) is wrong: both the cis and the trans isomers of 1,3-dimethylcyclobutane have a plane of symmetry, so there are only two stereoisomers, both achiral.
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