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Question

Which of the following compounds is most easily converted to a phenol when heated with aqueous NaOH solution?

A
Chlorobenzene
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B
4-Chloronitrobenzene
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C
2,4-Dinitrochlorobenzene
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D
2,4,6-Trinitrochlorobenzene
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Solution

The correct option is D 2,4,6-Trinitrochlorobenzene
The presence of electron withdrawing groups like NO2 at ortho and para positions with respect to the halogen, increases the reactivity of the haloarene. Chlorobenzene has no such group and converts to phenol at the highest temperature and pressure.

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