The compound that is the most difficult to protonate is:

H_{2} O

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H_{3} C - O H

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H_{3} C - O - C H_{3}

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P h - O H

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Solution

The correct option is D $P h - O H$
Due to the involvement of the lone pair of electrons in resonance in phenol, it will have positive charge (partial), hence the incoming proton will not be able to attack easily.

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