PrepRung

JEE Advanced 2017 Paper 2 · Chemistry · General Organic Chemistry and Isomerism · hard

The compound(s) that have exactly three stereoisomers in total (enantiomers counted separately, and meso forms counted as one) is(are)

One or more options correct

The compound(s) that have exactly three stereoisomers in total (enantiomers counted separately, and meso forms counted as one) is(are)
  1. A. 1,3-dimethylcyclohexane
  2. B. 1,2-dimethylcyclohexane
  3. C. 2,3-dichloropentane
  4. D. hexa-2,4-diene
Show answer and solution

Answer: A, B, D

Count each case. 1,3-Dimethylcyclohexane has two stereocentres with identical substituents: the ciscis isomer is meso (it has a mirror plane) and the transtrans isomer exists as a pair of enantiomers, giving 1+2=31+2=3 (A is correct). 1,2-Dimethylcyclohexane behaves the same way: ciscis is meso (flipping chair forms interconvert) and transtrans is chiral as an enantiomeric pair, total 3 (B is correct). 2,3-Dichloropentane has two stereocentres bearing different end groups (CH3\mathrm{CH_3} and C2H5\mathrm{C_2H_5}), so there is no meso form and the total is 22=42^2=4 (C is wrong). Hexa-2,4-diene has two stereogenic double bonds with identical ends, so EEEE, ZZZZ and EZEZ exist, and EZ=ZEEZ=ZE, giving 3 (D is correct).
Report a mistake

Original question written in the JEE Advanced 2017 Paper 2 pattern and checked twice for the correct answer. Not an official question paper. How we write and check questions · Corrections policy · Report a mistake