Phenols* - Acidity of phenols effect of
substituents on acidity
Garla Venkateswarlu
[Link]., (Ph. D.)
Asst. Professor
Dept of Pharma. Chemistry
School of Pharmacy
Sharda University
Greater Noida-201306.
Phenols
Phenols are the aromatic compounds. They contain hydroxyl groups directly linked to
the carbon atom of the aromatic nucleus.
These compounds are having a general formula as Ar-OH, in which ‘Ar’ represents the
aromatic ring and it may be the phenyl or substituted phenyl or some other aryl group
•General formula: C₆H₅OH
•Phenol is weakly acidic in nature and can donate a proton (H⁺) to form a phenoxide ion.
2. Acidity of Phenols
•The –OH group in phenol can lose a proton (H⁺) to form a phenoxide ion (C₆H₅O⁻).
•The phenoxide ion is resonance stabilized due to delocalization of the negative
charge over the aromatic ring.
Resonance in Phenoxide Ion:
•The lone pair of electrons on oxygen delocalizes into the benzene ring.
•This creates multiple resonance structures that stabilize the negative charge.
Effect of Substituents on Acidity of Phenol
Substituents on the benzene ring can either increase or decrease the acidity of phenol depending on their electron-
withdrawing or electron-donating nature.A. Electron-Withdrawing Groups (EWGs):(e.g., –NO₂, –Cl, –CN, –
COOH)
Increase the acidity of phenol.
These groups stabilize the phenoxide ion by delocalizing or pulling the negative charge.
Effect is stronger when positioned at ortho or para positions.
Example:
p-Nitrophenol is more acidic than phenol.
Reason: –NO₂ group stabilizes phenoxide ion by delocalizing negative charge through resonance and inductive
effects.
B. Electron-Donating Groups (EDGs):(e.g., –CH₃, –OCH₃, –OH, –NH₂)Decrease the acidity of phenol.
These groups destabilize the phenoxide ion by increasing electron density on the oxygen atom.
Especially pronounced at ortho and para positions.
Example:
p-Cresol (p-methyl phenol) is less acidic than phenol.
Reason: –CH₃ is an electron-donating group that destabilizes the phenoxide ion.
Order of Acidity (Examples):
p-Nitrophenol > o-Nitrophenol > Phenol > p-Cresol > p-Methoxyphenol
Qualitative tests, Structure and uses of
phenol, cresols, resorcinol, naphthols
Phenols
Phenols are the aromatic compounds. They contain hydroxyl groups directly linked to
the carbon atom of the aromatic nucleus.
These compounds are having a general formula as Ar-OH, in which ‘Ar’ represents the
aromatic ring and it may be the phenyl or substituted phenyl or some other aryl group
•General formula: C₆H₅OH
•Phenol is weakly acidic in nature and can donate a proton (H⁺) to form a phenoxide ion.
Aromatic Acids
Aromatic Amines
Synthetic uses of aryl diazonium salts
They are particularly useful in
dye and pigment production, and synthesizing a
range of aromatic compounds like aryl halides,
phenols, and cyanobenzenes.