Which of the following compounds is most easily converted to a phenol when heated with aqueous NaOH solution?(a) Chlorobenzene(b) 4-Chloronitrobenzene(c) 2,4-Dinitrochlorobenzene(d) 2,4,6-TrinitrochlorobenzeneThis question was addressed to me in a job interview.The doubt is from Haloalkanes & Haloarenes topic in portion Haloalkanes and Haloarenes of Chemistry – Class 12

Which of the following compounds is most easily converted to a phenol

1.	Which of the following compounds is most easily converted to a phenol when heated with aqueous NaOH solution?(a) Chlorobenzene(b) 4-Chloronitrobenzene(c) 2,4-Dinitrochlorobenzene(d) 2,4,6-TrinitrochlorobenzeneThis question was addressed to me in a job interview.The doubt is from Haloalkanes & Haloarenes topic in portion Haloalkanes and Haloarenes of Chemistry – Class 12
Answer» The correct answer is (d) 2,4,6-Trinitrochlorobenzene To elaborate: 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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