The correct order of decreasing acidity of nitrophenols will be:
A
m−nitrophenol>p−nitrophenol>o−nitrophenol
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B
o−nitrophenol>m−nitrophenol>p−nitrophenol
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C
p−nitrophenol>m−nitrophenol>o−nitrophenol
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D
p−nitrophenol>o−nitrophenol>m−nitrophenol
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Solution
The correct option is Dp−nitrophenol>o−nitrophenol>m−nitrophenol −NO2 group at ortho and para position withdraws electrons of the O−H bond towards itself by the stronger −R effect while the −NO2 group at m-position withdraw electrons of the O−H bond by the weaker effect.
Thus, ortho and para nitrophenols are more acidic than meta nitrophenol is little less acidic than p-nitrophenol due to intramolecular H-bonding which makes loss of a proton little more difficult.