NEETChemistryGeneral Organic Chemistry
Which of the following alkylbenzenes does NOT exhibit hyperconjugation with the benzene ring?
Options
- Atert-Butylbenzene
- BIsopropylbenzene
- CEthylbenzene
- 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