有機化學第18章_2009 [&

有&ae - 1 18 Ethers and Epoxides Thiols and Sulfides 醚與環氧化物;硫醇與硫化物 醚與環氧化物;硫醇與硫化物

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Unformatted text preview: 1 18: Ethers and Epoxides; Thiols and Sulfides 醚與環氧化物;硫醇與硫化物 醚與環氧化物;硫醇與硫化物 Thiols (R–S–H) and sulfides (R–S–R ′ ) Based on McMurry’s Organic Chemistry , 7 th edition Ethylene oxide The smallest cyclic ether. Dimethyl ether An aerosol spray propellant . 2 2 Epoxides 環氧化物 An epoxide is a cyclic ether with only three ring atoms. 3 Thiols and Sulfides 硫醇與硫化物 Thiols (R–S–H) and sulfides (R–S–R ′ ) are sulfur (for oxygen) analogs of alcohols and ethers Dimethyl Sulfide CH 3-S-CH 3 4 3 3 3 Why this Chapter? To finish covering functional groups with C-O and C-S single bonds Focus on ethers and look at thiols and sulfides before going on to C=O 5 OUTLINE ¡ Names and Properties of Ethers ¡ Synthesis of Ethers ¡ Reactions of Ethers: Acidic Cleavage ¡ Reactions of Ethers: 6 ¡ Reactions of Ethers: Claisen Rearrangement ¡ Cyclic Ethers: Epoxides 4 OUTLINE ¡ Reactions of Epoxides: Ring-Opening ¡ Crown Ethers ¡ Thiols and Sulfides ¡ Spectroscopy of Ethers 7 ¡ Spectroscopy of Ethers 18.1 Names and Properties of Ethers Simple ethers are named by identifying the two organic substituents and adding the word ether 8 5 Names of Ethers II If other functional groups are present, the ether part is considered the ether part is considered an alkoxy substituent 9 Properties of Ethers R–O–R ~ tetrahedral bond angle (112 ° in dimethyl ether (112 in dimethyl ether) 10 Oxygen is sp 3-hybridized Oxygen atom gives ethers a slight dipole moment 6 11 P. 18.1 12 7 P. 18.1 13 18.2 Synthesis of Ethers Diethyl ether prepared industrially by sulfuric acid–catalyzed dehydration of ethanol only with primary alcohols 14 2 o and 3 o alcohols dehydrate by an E1 mechanism to yield alkenes Only for symmetrical ethers 8 P. 18.2 15 The Williamson Ether Synthesis Reaction of metal alkoxides (1 o 2 o or 3 o ) and Best method for the preparation of ethers Unsymmetrical ethers primary alkyl halides and tosylates primary alkyl halides 16 Alkoxides prepared by reaction of an alcohol with a strong base such as sodium hydride, NaH 9...
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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&ae - 1 18 Ethers and Epoxides Thiols and Sulfides 醚與環氧化物;硫醇與硫化物 醚與環氧化物;硫醇與硫化物

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