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NEETChemistryGeneral Organic Chemistry

Which of the following alkylbenzenes does NOT exhibit hyperconjugation with the benzene ring?

Options

  1. Atert-Butylbenzene
  2. BIsopropylbenzene
  3. CEthylbenzene
  4. DToluene

Correct answer

A. tert-Butylbenzene

Step-by-step solution

Hyperconjugation in alkylarenes requires the presence of at least one -hydrogen on the sp^3 hybridized carbon directly attached to the sp^2 carbon of the aromatic ring. In tert-butylbenzene, the carbon atom attached to the benzene ring is bonded to three methyl groups and has no -hydrogen. Therefore, it does not exhibit hyperconjugation. Toluene has three -hydrogens, ethylbenzene has two -hydrogens, and isopropylbenzene has one -hydrogen, allowing them to show hyperconjugation. Answer: tert-Butylbenzene

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