JEE Main 2024 · 9 April · evening · Single correct · +4 / −1

Total number of stereo isomers possible for the given structure :

JEE Main PYQ figure
  1. (a) 4
  2. (b) 2
  3. (c) 8
  4. (d) 3
Answer and solution

Answer (c) 8

Solution

Chemistry ma’am · 3 steps

Find every stereo unit, one chiral carbon and two C=C, and since the molecule is unsymmetrical, use 2ⁿ.

  1. Read the structure. Number the chain from the left: CH₃-C(Br)=CH-CH₂-CH(Br)-C(CH₃)=C(Br)-CH₃, that is C1 to C8. Now check each double bond and each sp³ carbon for stereo possibility.
    Stereo unitGroups to compareStereo?
    C₂=C₃C2: CH₃, Br; C3: H, CH₂RYes, both ends unlike, so E/Z
    C5 (CHBr)H, Br, CH₂CH=C(Br)CH₃, C(CH₃)=C(Br)CH₃Yes, four different groups, so chiral
    C₆=C₇C6: CH₃, CHBrR; C7: Br, CH₃Yes, both ends unlike, so E/Z
  2. Count them. There are n = 3 stereo units, each with two arrangements. The two ends of the molecule are different, so no meso form or symmetry cuts the count down.

    Stereoisomers = 2ⁿ = 2³ = 8

  3. So. The structure has 8 stereoisomers, option (c).

The idea to keep. Count chiral centres and stereo double bonds together as n. If the molecule has no symmetry, the total is 2ⁿ. Only a symmetrical molecule needs the reduced formula.

Answer from the NTA final answer key. Solution by PrepWiser.

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Asked about 180 times in JEE Main since 2020. This question is from 2024.