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Question

The compound that is most difficult to protonate is:

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A
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B
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C
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D
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Solution

The correct option is C
Due to involvement of lone pair of electrons of oxygen atom in resonance with phenyl ring, it will have positive charge (partial), hence incoming proton will not be able to attack easily on phenol.

In all other compounds the lone pairs of electrons are localised so it can be easily protonated.

Hence, option (d) is correct.

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