JEE Main 2024 · 30 January · evening · Numerical answer · +4 / −1

Number of geometrical isomers possible for the given structure is/are _________.

JEE Main PYQ figure
Answer and solution

Answer 4

Solution

Chemistry ma’am · 3 steps

Both end bonds count, but the middle bond counts only when its two arms differ in configuration.

  1. End double bonds. Each terminal C=C has H and D on one carbon, and CH₃ and the CH₂ chain on the other. H and D are different groups, so each end bond can be E or Z.
  2. Middle double bond. One carbon of the middle bond carries H and CH₃. The other carries two CH₂-C(CH₃)=CHD arms with the same atoms. So the middle bond shows geometrical isomerism only when those two arms have different configurations.
    End bondsTwo arms on middle carbonMiddle bondIsomers
    E and Eidenticalnot stereogenic1
    Z and Zidenticalnot stereogenic1
    one E, one ZdifferentE or Z2
  3. So. Left E with right Z is the same molecule as left Z with right E, read from the other end. The total is 1 + 1 + 2 = 4 geometrical isomers.

The common slip: 8. Treating all three double bonds as independent gives 2³ = 8. That misses that the middle bond is stereogenic only when its two arms differ.

The idea to keep. When two groups on a double-bond carbon have the same atoms but can differ in configuration, that bond is stereogenic only in the isomers where they differ. Count case by case, not with 2ⁿ.

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

Study General Organic Chemistry (GOC)

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