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Basics of Organic Chemistry question

2024 · 6 Apr · Shift 2 · Q19
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Basics of Organic Chemistry question

2024 · 6 Apr · Shift 2 · Q19

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The incorrect statement regarding the geometrical isomers of 2-butene is :
  1. A
    cis-2-butene and trans-2-butene are not interconvertible at room temperature.
  2. B
    trans-2-butene is more stable than cis-2-butene.
  3. C
    cis-2-butene has less dipole moment than trans-2-butene.
  4. D
    cis-2-butene and trans-2-butene are stereoisomers.
View written solutionFree

Correct answer: C

  1. Identify the geometrical isomers of 222-butene

    Structure of 222-butene is: CH3−CH=CH−CH3\mathrm{CH_3-CH=CH-CH_3}CH3​−CH=CH−CH3​

    Since each carbon of the double bond has two different groups attached, it shows geometrical isomerism:

    • cis-2-butene: both CH3\mathrm{CH_3}CH3​ groups on the same side
    • trans-2-butene: both CH3\mathrm{CH_3}CH3​ groups on opposite sides
  2. Check each statement

    Option A:

    "cis-2-butene and trans-2-butene are not interconvertible at room temperature."

    Interconversion of cis and trans forms would require rotation about the C=C\mathrm{C=C}C=C double bond, but rotation is restricted because of the π\piπ bond.

    Therefore, under normal conditions at room temperature, they are not interconvertible.

    So, A is correct.

    Option B:

    "trans-2-butene is more stable than cis-2-butene."

    In trans-2-butene, the two bulky CH3\mathrm{CH_3}CH3​ groups are on opposite sides, so steric repulsion is less.

    Hence, trans-2-butene is more stable than cis-2-butene.

    So, B is correct.

    Option C:

    "cis-2-butene has less dipole moment than trans-2-butene."

    In cis-2-butene, the bond dipoles do not cancel completely, so it has a non-zero dipole moment.

    In trans-2-butene, due to symmetry, bond dipoles largely cancel out, so its dipole moment is very small (approximately zero).

    Therefore: μ(cis-2-butene)>μ(trans-2-butene)\mu(\text{cis-2-butene}) > \mu(\text{trans-2-butene})μ(cis-2-butene)>μ(trans-2-butene)

    The statement says cis has less dipole moment than trans, which is wrong.

    So, C is incorrect.

    Option D:

    "cis-2-butene and trans-2-butene are stereoisomers."

    Geometrical isomers are a type of stereoisomers because they differ in spatial arrangement of atoms.

    So, D is correct.

  3. Conclusion

    The incorrect statement is: C\boxed{\text{C}}C​

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