Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Consider the following statements regarding the stability of the given reaction intermediates: Statement (i): is more stable than . Statement (ii): is more stable than . Choose the correct option:
Options
- ABoth statements (i) and (ii) are correct
- BBoth statements (i) and (ii) are incorrect
- CStatement (i) is correct and statement (ii) is incorrect
- DStatement (i) is incorrect and statement (ii) is correct
Correct answer
A. Both statements (i) and (ii) are correct
Step-by-step solution
For the intermediates in statement (i), the positive charge in the first structure can be delocalized onto the carbon bearing the - OH group. The - OH group stabilizes the carbocation through a strong +M effect by donating a lone pair, forming a resonance structure with complete octets. In the second structure, the - CH ₃ group stabilizes the positive charge through weaker +I and hyperconjugation effects. Since the +M effect of - OH is stronger than the electron-donating effects of - CH ₃ , the first intermediate i