有機化學第17ç« ï&f

有機化學第17ç« ï&f

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Unformatted text preview: 1 Chapter 17: Alcohols and Phenols Alcohols and Phenols 醇與酚 Based on McMurry’s Organic Chemistry , 7 th edition Alcohols and Phenols Alcohols contain an OH group connected to a saturated C (sp 3 ) They are important solvents and synthesis intermediates 2 22 章 Phenols contain an OH group connected to a carbon in a benzene ring 2 Why this Chapter? To begin to study oxygen-containing functional groups These groups lie These groups lie at the heart of biological chemistry 3 R = (CH 2 ) 14 CH 3 R = (CH 2 ) 7 CH=CH(CH 2 ) 5 CH 3 R = (CH 2 ) 7 CH=CHCH 2 CH=CH(CH 2 ) 2 CH 3 R = (CH 2 ) 7 CH=CHCH 2 CH=CHCH=CHCH 3 R = (CH 2 ) 7 CH=CHCH 2 CH=CHCH 2 CH=CH 2 OUTLINE ¡ Naming Alcohols and Phenols ¡ Properties of Alcohols and Phenols ¡ Preparation of Alcohols: A Review ¡ Alcohols from Reduction of Carbonyl Compounds 4 ¡ Alcohols from Reaction of Carbonyl Compounds with Grignard Reagents 3 OUTLINE ¡ Reactions of Alcohols ¡ Oxidation of Alcohols ¡ Protection of Alcohols ¡ Phenols and Their Uses ¡ Reactions of Phenols 5 ¡ Spectroscopy of Alcohols and Phenols Methanol 甲醇 CH 3 OH, called methyl alcohol (wood alcohol) , is a common solvent, a fuel additive, produced in large quantities Toxic to human Blindness (15ml) , Death (100-250 ml) 6 4 Methanol as a starting Material ¡ Formaldehyde ¡ Acetic acid CH 3 OH + CO → CH 3 COOH ¡ Methyl tert-butyl ether (MTBE) 2 CH 3 OH + O 2 → 2 H 2 CO + 2 H 2 O 7 Ethanol 乙醇 CH 3 CH 2 OH, called ethyl alcohol, is a solvent, fuel, beverage 8 5 Phenols 酚 Phenol, C 6 H 5 OH (“phenyl alcohol”) has diverse uses - it gives its name to the general class of compounds to the general class of compounds 9 Oil of wintergreen 鹿蹄草油 OAK , IVY Resin from Phenol 10 6 Urushiols R = (CH 2 ) 14 CH 3 or R = (CH 2 ) 7 CH=CH(CH 2 ) 5 CH 3 or R = (CH 2 ) 7 CH=CHCH 2 CH=CH(CH 2 ) 2 CH 3 or 11 R = (CH 2 ) 7 CH=CHCH 2 CH=CHCH=CHCH 3 or R = (CH 2 ) 7 CH=CHCH 2 CH=CHCH 2 CH=CH 2 and others poison oak urushiol contains mostly catechols with C 17 side chains, but poison ivy and poison sumac contain mostly catechols with C 15 side chains General Classifications of Alcohols General classifications of alcohols based on substitution on C to which OH is attached Methyl (C has 3 H’s), Primary (1 ° ) (C has two H’s, one R), Secondary (2 ° ) (C has one H, two R’s), Tertiary (3 ° ) (C has no H, 3 R’s), 12 7 IUPAC Rules for Naming Alcohols ¡ Select the longest carbon chain containing the hydroxyl group, and derive the parent name by replacing the - e ending of the corresponding alkane with - ol ¡ Number the chain from the end nearer the hydroxyl group ¡ Number substituents according to position on chain, listing the substituents in alphabetical order 13 Many Alcohols Have Common Names 8 Naming Phenols Use “phenol” as the parent hydrocarbon name, not benzene Name substituents on aromatic ring by their position from OH 15 P. 17.1 16 9 P. 17.1 17 P. 17.2 18 10 17.2 Properties of Alcohols and Phenols: The structure around O of the alcohol or phenol...
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This note was uploaded on 11/11/2010 for the course CHE CH2005 taught by Professor 曹恒光 during the Spring '10 term at National Central University.

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有機化學第17ç« ï&f

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