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Question
Which of the following compound is most acidic?
Which of the following compound is most acidic?
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Solution
The correct option is C p-nitrophenol
Phenols are more acidic than alcohol & water due to
(i) the higher electronegativity of sp2 carbon to which OH group is attached.
(ii) the electron withdrawing nature of the benzene ring.
Conjugate base of phenol is stabilised by conjugation of negative charge in the ring. Acidic strength is inversely propotional to EDGs and directly propotional to EWGs.
In o-cresol there is presence of an EDG (−CH3). Hence, it will be less acidic than phenol. Structure of o-cresol-
Structure of anisole
It will be less acidic than phenol as here no polar bond is present.
Because of the electron withdrawing effect of −NO2 group, p-nitrophenol is most acidic than phenol. Thus the acidity order will be p-nitrophenol>phenol>o-cresol>anisole. Hence p-nitrophenol is the most acidic.
Phenols are more acidic than alcohol & water due to
(i) the higher electronegativity of sp2 carbon to which OH group is attached.
(ii) the electron withdrawing nature of the benzene ring.
Conjugate base of phenol is stabilised by conjugation of negative charge in the ring. Acidic strength is inversely propotional to EDGs and directly propotional to EWGs.
In o-cresol there is presence of an EDG (−CH3). Hence, it will be less acidic than phenol. Structure of o-cresol-
Structure of anisole
It will be less acidic than phenol as here no polar bond is present.Because of the electron withdrawing effect of −NO2 group, p-nitrophenol is most acidic than phenol. Thus the acidity order will be p-nitrophenol>phenol>o-cresol>anisole. Hence p-nitrophenol is the most acidic.
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