Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Which of the following alcohols forms the most stable carbocation upon the loss of an OH ⁻ ion?
Options
- A( CH ₃ )₃ C - CH ₂ OH
- BC ₆ H ₅ CH ₂ CH ₂ OH
- CC ₆ H ₅ CH ₂ OH
- DCH ₃ CH ₂ CH ₂ CH ₂ OH
Correct answer
C. C ₆ H ₅ CH ₂ OH
Step-by-step solution
Loss of an OH ⁻ ion from the given alcohols results in the formation of the following carbocations: (A) ( CH ₃)₃ C - CH ₂⁺ : Primary carbocation, lacks resonance stabilization. (B) C ₆ H ₅ CH ₂ CH ₂⁺ : Primary carbocation, lacks resonance stabilization as the positive charge is not adjacent to the benzene ring. (C) C ₆ H ₅ CH ₂⁺ (Benzyl carbocation): Highly stabilized by resonance due to the delocalization of the positive charge over the benzene ring. (D) CH ₃ CH ₂ CH ₂ CH ₂⁺ : Primary carbocation, lacks resonance