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Chapter 24 Phenols

Chapter 24 Phenols. 24.1 Nomenclature. OH. CH 3. Cl. Nomenclature. named on basis of phenol as parent substituents listed in alphabetical order lowest numerical sequence: first point of difference rule. 5- Chloro -2- methyl phenol. OH. OH. OH. OH. OH. OH. Nomenclature.

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Chapter 24 Phenols

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  1. Chapter 24Phenols

  2. 24.1Nomenclature

  3. OH CH3 Cl Nomenclature • named on basis of phenol as parent • substituents listed in alphabetical order • lowest numerical sequence: first point ofdifference rule 5-Chloro-2-methylphenol

  4. OH OH OH OH OH OH Nomenclature 1,2-Benzenediol 1,3-Benzenediol 1,4-Benzenediol (common name:pyrocatechol) (common name:resorcinol) (common name:hydroquinone)

  5. OH CO2H Nomenclature • name on basis of benzoic acid as parent • higher oxidation states of carbon outrankhydroxyl group p-Hydroxybenzoic acid

  6. 24.2Structure and Bonding

  7. Structure of Phenol • phenol is planar • C—O bond distance is 136 pm, which isslightly shorter than that of CH3OH (142 pm)

  8. 24.3Physical Properties The OH group of phenols allows hydrogen bondingto other phenol molecules and to water.

  9. O O H Hydrogen Bonding in Phenols

  10. Physical Properties (Table 24.1) Compared to compounds of similar size andmolecular weight, hydrogen bonding in phenol raises its melting point, boiling point, andsolubility in water.

  11. Physical Properties (Table 24.1) C6H5CH3 C6H5OH C6H5F Molecular weight 92 94 96 Melting point (°C) –95 43 –41 Boilingpoint (°C,1 atm) 111 132 85 Solubility inH2O (g/100 mL,25°C) 0.05 8.2 0.2

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