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Q. Which one of the following compounds, is most acidic ?

UPSEEUPSEE 2007

Solution:

Phenols are much more acidic than alcohol due to the stabilisation of phenoxide ion resonance.
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Phenoxide ion is stabilized due to following resonating structures :
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While, in alcohols
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Ortho nitrophenol is most acidic because in $—NO_2$ electron attracting group is attached to ortho position which helps in stabilizing the negative charge on the oxygen of phenoxide ion. Hence, due to this reason acidic character of phenol is increased, while on attachment of $—CH_3$ group (electron donating group) acidic strength of phenol is decreased in cresol due to the destabilization of phenoxide ion.