浙江大学马成有机化学乙课件 Chapter_16_Phenol_and_Benzoquinone.pdfVIP

Chapter 16 Phenol and Benzoquinone 2009/9/13 1 Summary • Phenol is derived from the old name for benzene (phene), to include the suffix that indicates it possesses a hydroxyl group (-ol). CAUTION: phenol (C H -OH) ; phenyl (C H -) 6 5 6 5 • Acidity of Phenols • Substitution of the Hydroxyl Hydrogen (forming ether) • Oxidation of Phenols 2009/9/13 2 16.1 Structure and Nomenclature of Phenol 1. Compounds in which a hydroxyl group is bonded to an aromatic ring are called phenol 2 2. Structure: O atom in –OH sp hybridization 3. Nomenclature: Functional group suffix = -common - phenol, systematic - benzenol Functional group prefix = hydroxy- 2009/9/13 3 4. Reactivity • Comparing alcohols and phenols, so for all practical purposes substitution and/or elimination of the phenolic hydroxyl group does not occur • Substitution of the Hydroxyl Hydrogen 5. Acidity: • Phenols are more acidic (pK 10) than alcohols (pK 16 - a a 20), but less acidic than carboxylic acids (pKa»5) Due to electronic effect and hydrogen bond • Resonance • Inductive effect 2009/9/13 4 • Exp. 2009/9/13 5 16.2 Preparation of Phenols • Summary for the preparation of phenol 2009/9/13 6 16