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Basics of Organic Chemistry question

2008 · Shift 0 · Q14
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Basics of Organic Chemistry question

2008 · Shift 0 · Q14

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The electrophile, E⊕{E^ \oplus }E⊕ attacks the benzene ring to generate the intermediate σ−\sigma -σ− complex. Of the following, which σ−\sigma -σ− complex is lowest energy?
  1. A
    AIEEE 2008 Chemistry - Basics of Organic Chemistry Question 228 English Option 1
  2. B
    AIEEE 2008 Chemistry - Basics of Organic Chemistry Question 228 English Option 2
  3. C
    AIEEE 2008 Chemistry - Basics of Organic Chemistry Question 228 English Option 3
  4. D
    AIEEE 2008 Chemistry - Basics of Organic Chemistry Question 228 English Option 4
View written solutionFree

Correct answer: B

  1. Key idea: stability of the σ\sigmaσ-complex in electrophilic aromatic substitution

    In electrophilic substitution on benzene, the electrophile E⊕E^\oplusE⊕ first attacks the ring to form a σ\sigmaσ-complex (arenium ion).

    The lower the energy of this intermediate, the more stable it is.

  2. What makes a σ\sigmaσ-complex more stable?

    A σ\sigmaσ-complex is stabilized when the positive charge in the intermediate is:

    • delocalized effectively, and/or
    • stabilized by electron-donating groups through resonance or hyperconjugation.

    It is destabilized by electron-withdrawing groups.

  3. Comparison principle for substituted benzenes

    Among possible σ\sigmaσ-complexes, the one with the greatest resonance stabilization and best electron donation toward the positively charged ring will be the lowest-energy intermediate.

  4. Identifying the best option

    From the given choices, option B corresponds to the σ\sigmaσ-complex in which the carbocation is most effectively stabilized by resonance/electron donation.

    Therefore, this σ\sigmaσ-complex has the lowest energy.

  5. Conclusion

    Hence, the correct option is: B\boxed{\text{B}}B​

  6. Verification with stored answer

    Stored correct answer: B

    Our derived answer: B

    So they agree.

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