Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Which of the following represents the most stable arenium ion?
Correct answer
2
Step-by-step solution
In the electrophilic aromatic substitution of toluene, the stability of the intermediate arenium ion (sigma complex) determines the major product. The methyl group ( -CH₃ ) is an electron-donating group due to its +I (inductive) effect and hyperconjugation. It stabilizes the carbocation intermediate when the positive charge is located on the carbon atom to which it is attached (the ipso carbon). Let us analyze the given resonance structures: In structures (A), (B), and (D), the positive charge is located on seconda