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Lecture 7 - Phenols OH McMurry Chapter 17 1 Overview...

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Phen o ls OH 1 McMurry Chapter 17
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Overview • Introduction: Some important phenols Physical properties • ABENOR Syntheses of Phenol 2 Reactions of Phenols (only 5!! and we covered 4 of these in Chem 2203 – Organic I)
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Phen o ls (Aromatic Alcoh o ls) OH H O H H 3 Phenols are Enols of unsaturated cyclohexanones. Enol Tautomer is highly stabilized due to ______________.
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OH Phenol = Phen yl Alcoh ol (“Carbolic acid ”) The Methyl-phenol (Cresol) family 4 OH OH OH Ortho- cresol meta- cresol para- cresol creosote
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Phenols vrs Bacteria Joseph Lister 5
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OH OH O O [O] Catechol Ortho - BenzoQuinone The Dihydroxybenzene Family + H 2 6 OH OH O O [O] Hydroquinone Para- BenzoQuinone Resorcinol [H] + H 2
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Bombardier Beetle uses Phenol Chemistry in Self-Defence 7 Tom Eisner OH OH O O [O] Hot, pulsed, spray
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Tyrosine is a phenolic Amino acid tyrosinase OH O tyrosinase 8 Polymerization Leads to coloured Pigments eg. browning of fruit
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Lignin: Complex polymer of cross-linked phenolic monomers: (Earth’s 2 nd most abundant molecule!) 9 radical coupling HO . Me Me
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Estrone: An important steroidal phenol 10
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Natural Aromatase Exemestane Substrate Anti-cancer drug 11
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Bisphenol A and Estrogens 12 A Health Canada study of canned pop has found the vast majority of the drinks contain the chemical bisphenol A, a substance that imitates the female hormone estrogen and is banned in baby bottles Estrone Bisphenol
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Vitamin E: Antixoxidant: Fountain of Youth? Reactive Oxygen Species (ROS) 13 eg. . OOR Critically Important!
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Resveratrol: Another antioxidant? 14
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Monomethyl Catechols: More tasty antioxidants Capsaicin 15 Eugenol (cloves) Vanillin Curcumin, Curry powder
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Physical Properties of phenol 1. Boiling point and melting point similar to corresponding cyclic aliphatic alcohols H-bonding, compact shape 16 OH vs.
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