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The compound that is most difficult to protonate is:

1. H–O–H
2. H3C–O–H
3. H3C–O–CH3
4. Ph–O–H

Correct answer: Ph–O–H

Solution

Phenol (Ph–O–H) is the most difficult to protonate because the lone pair on oxygen is delocalized into the aromatic ring, reducing its availability for protonation.

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