Chapter16_4 - Chapter 16 Ethers, Epoxides, and Sulfides...

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Chem 212 B. R. Kaafarani 1 Chapter 16 Ethers, Epoxides, and Sulfides
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Chem 212 B. R. Kaafarani 2 Name as alkoxy derivatives of alkanes. CH 3 O CH 2 CH 3 Methoxy ethane CH 3 CH 2 O CH 2 CH 3 Ethoxy ethane CH 3 CH 2 O CH 2 CH 2 CH 2 Cl 3-Chloro-1- ethoxy propane Substitutive IUPAC Names of Ethers 16.1. Nomenclature of Ethers, Epoxides, and Sulfides
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Chem 212 B. R. Kaafarani 3 CH 3 O CH 2 CH 3 Ethyl methyl ether CH 3 CH 2 O CH 2 CH 3 Di ethyl ether CH 3 CH 2 O CH 2 CH 2 CH 2 Cl 3-Chloropropyl ethyl ether Functional Class IUPAC Names of Ethers Name the groups attached to oxygen in alphabetical order as separate words; "ether" is last word.
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Chem 212 B. R. Kaafarani 4 CH 3 S CH 2 CH 3 Methylthio ethane CH 3 CH 2 S CH 2 CH 3 Ethylthio ethane (Methylthio) cyclopentane SCH 3 Name as alkylthio derivatives of alkanes Substitutive IUPAC Names of Sulfides
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Chem 212 B. R. Kaafarani 5 Cyclopentyl methyl sulfide CH 3 S CH 2 CH 3 Ethyl methyl sulfide CH 3 CH 2 S CH 2 CH 3 Diethyl sulfide S CH 3 Functional Class IUPAC Names of Sulfides Analogous to ethers, but replace “ether” as last word in the name by “sulfide.”
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Chem 212 B. R. Kaafarani 6 Oxirane (Ethylene oxide) Oxetane Oxolane (Tetrahydrofuran) Oxane (Tetrahydropyran) 1,4-Dioxane O O O O O O Names of Cyclic Ethers
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Chem 212 B. R. Kaafarani 7 Thiirane Thietane Thiolane Thiane S S S S Names of Cyclic Sulfides
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Chem 212 B. R. Kaafarani 8 16.2. Structure and Bonding in Ethers and Epoxides Bent geometry at oxygen analogous to water and alcohols, i.e. sp 3 hybidization
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Chem 212 B. R. Kaafarani 9 112° H O H 105° 108.5° (CH 3 ) 3 C O C(CH 3 ) 3 132° H O CH 3 CH 3 O CH 3 Bond angles at oxygen are sensitive to steric effects Dimethyl ether Di- tert -butyl ether Water Methanol
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Chem 212 B. R. Kaafarani 10 Most stable conformation of diethyl ether resembles pentane (all staggered anti conformation). An oxygen atom affects geometry in much the same way as a CH 2 group
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Chem 212 B. R. Kaafarani 11 Most stable conformation of tetrahydropyran resembles cyclohexane (chair conformation). An oxygen atom affects geometry in much the same way as a CH 2 group
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Chem 212 B. R. Kaafarani 12 boiling point 36°C 35°C 117°C O OH Ethers resemble alkanes more than alcohols with respect to boiling point. 16.3. Physical Properties of Ethers Dispersion forces are major contributors to intermolecular attractions in ethers as in alkanes. Hydrogen bonding possible in alcohols; not possible in alkanes or ethers.
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Chem 212 B. R. Kaafarani 13 Solubility in water (g/100 mL) very small 9 7.5 O OH Ethers resemble alcohols more than alkanes with respect to solubility in water Hydrogen bonding to water possible for ethers and alcohols; not possible for alkanes.
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Chem 212 B. R. Kaafarani 14 Structure cyclic polyethers derived from repeating —OCH 2 CH 2 — units.
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Chapter16_4 - Chapter 16 Ethers, Epoxides, and Sulfides...

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