lecture 18 - 18: Ethers and Epoxides; Thiols and Sulfides...

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18: Ethers and Epoxides; Thiols and Sulfides Based on McMurry’s Organic Chemistry , 7 th edition
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2 Ethers and Their Relatives An ether has two organic groups (alkyl, aryl, or vinyl) bonded to the same oxygen atom, R–O–R Diethyl ether is used industrially as a solvent Tetrahydrofuran (THF) is a solvent that is a cyclic ether Thiols (R–S–H) and sulfides (R–S–R ) are sulfur (for oxygen) analogs of alcohols and ethers
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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
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4 18.1 Names and Properties of Ethers Simple ethers are named by identifying the two organic substituents and adding the word ether If other functional groups are present, the ether part is considered an alkoxy substituent R–O–R ~ tetrahedral bond angle (112° in dimethyl ether) Oxygen is sp 3 -hybridized Oxygen atom gives ethers a slight dipole moment
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5 18.2 Synthesis of Ethers Diethyl ether prepared industrially by sulfuric acid–catalyzed dehydration of ethanol – also with other primary alcohols
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6 The Williamson Ether Synthesis Reaction of metal alkoxides and primary alkyl halides and tosylates Best method for the preparation of ethers Alkoxides prepared by reaction of an alcohol with a strong base such as sodium hydride, NaH
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7 Silver Oxide-Catalyzed Ether Formation Reaction of alcohols with Ag 2 O directly with alkyl halide forms ether in one step Glucose reacts with excess iodomethane in the presence of Ag 2 O to generate a pentaether in 85% yield
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8 Alkoxymercuration of Alkenes React alkene with an alcohol and mercuric acetate or
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lecture 18 - 18: Ethers and Epoxides; Thiols and Sulfides...

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