The compound that is most difficult to protonate is:

- A1
- B2
- C3
- D4
Solution & Step-by-step Explanation
Protonation involves a lone pair of electrons on oxygen.
In Phenol (C
6
H
5
OH), the lone pair on oxygen is involved in resonance with the benzene ring. This delocalization makes the lone pair less available for protonation. In water, methanol, and ether, the lone pairs are localized and more available.
In Phenol (C
6
H
5
OH), the lone pair on oxygen is involved in resonance with the benzene ring. This delocalization makes the lone pair less available for protonation. In water, methanol, and ether, the lone pairs are localized and more available.