2009_12abPhenols - Chem 2204/2206/2208 Wednesday Mar 4...

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Chem 2204/2206/2208 Wednesday Mar. 4 Lecture 12a Phenols Friday Mar 6 Lecture 12b Phenols TODAY! Wednesday Mar 11 Lecture 13 Amines (I) Friday Mar 13 Lecture 14 Amines (II). 1 Test 2 (Carboxylic Acids) . Test 2 solutions are posted on http://http-server.carleton.ca/~pbuist/ . Pick up your test after class..
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Phen o ls OH 2 McMurry Chapter 17
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Overview • Introduction: Some common phenols Physical properties • ABENOR Syntheses of Phenol 3 Reactions of Phenols (only 5!! and we covered 4 of these in first term)
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Phen o ls (Aromatic Alcoh o ls) OH H O H H 4 Phenols are Enols of unsaturated cyclohexanones. Enol Tautomer is highly stabilized due to ___ ___________.
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OH “Carbolic acid ” = Phenol ( Phenyl alcohol) The Methyl-phenol (Cresol) family 5 OH OH OH Ortho- cresol meta- cresol para- cresol creosote
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Phenols vrs Bacteria Joseph Lister 6
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OH OH O O [O] Catechol Ortho - BenzoQuinone The Dihydroxybenzene Family + H 2 7 OH OH O O [O] Hydroquinone Para- BenzoQuinone Resorcinol [H] + H 2
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Bombardier Beetle uses Phenol Chemistry in Self-Defence 8 Tom Eisner OH OH O O [O] Hot, pulsed, spray
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Tyrosine is a phenolic Amino acid tyrosinase OH O tyrosinase 9 Polymerization Leads to coloured Pigments eg. browning of fruit
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Lignin: Complex polymer of cross-linked phenolic monomers: (2 nd most abundant molecule!) 10 radical coupling HO . Me Me
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Estrone: An important steroidal phenol 11
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Natural Aromatase Exemestane Substrate Anti-cancer drug 12
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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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