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ORAGANIC CHEMISTRY
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PHENOLSPHENOL
🠹 Phenol are the aromatic compounds having hydroxyl group (-OH) directly attached to
benzene ring. ELECTRONIC STRUCTURE OF PHENOL
🠹 In phenols the –OH group is attached to sp2 hybrid carbon of an aromatic ring and the
oxygen atom of the hydroxyl group has two lone pairs of electrons and the bond angle in
phenol is 109o. The C-O bond length in phenol (136pm) is slightly less than in
methanol(412pm) due to resonance in aromatic ring of phenol
🠹 Phenol has dipole moment 1.54D where as methanol has dipole moment 1.71D. This
smaller dipole moment of phenol is due to the electron attracting effect of phenyl
group in contrast to the electron releasing effect of methyl ( or alkyl) group in alcohol
CLASSIFICATION OF PHENOL
🠹 Phenols are classified as mono, di and trihydric phenols according to the number of
hydroxyl groups attached to the aromatic ring.
1. Monohydric phenols
2. Dihydric phenols
3. Trihydric phenols
,GENERAL METHODS OF PREPARATION OF PHENOLS
1. Alkali fusion of sulphonates
Sodium salt of aryl sulphonic acids on fusion with sodium hydroxide at 300-350oC yield
phenol
The above reaction is laboratory method for preparation of phenol
2. Hydrolysis of diazonium salt
3. Hydrolysis of aryl halides ( Dow’s process)
🠹 Aryl halides on hydrolysis yield phenol but the process is not so simple because halogen
atom attached to benzene ring does not undergo SN2 reaction since C-X bond is resonance
stabilized. Hence reaction takes place at high pressure and elevated pressure.
, 🠹 However if some electron withdrawing group is attached to benzene ring, then reaction
conditions get relaxed
4. Decarboxylation of salicylic acid
5. Oxidation of Grignard reagent
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