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Chapter 16 Ethers, Epoxides, and Sulfides

Chapter 16 Ethers, Epoxides, and Sulfides. 16.1 Nomenclature of Ethers, Epoxides, and Sulfides. CH 3 O CH 2 CH 3. CH 3 CH 2 O CH 2 CH 2 CH 2 Cl. methoxy ethane. 1-chloro-3- ethoxy propane. CH 3 CH 2 O CH 2 CH 3. ethoxy ethane. Substitutive IUPAC Names of Ethers.

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Chapter 16 Ethers, Epoxides, and Sulfides

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  1. Chapter 16Ethers, Epoxides, and Sulfides

  2. 16.1Nomenclature of Ethers, Epoxides, and Sulfides

  3. CH3OCH2 CH3 CH3CH2OCH2CH2CH2Cl methoxyethane 1-chloro-3-ethoxypropane CH3CH2OCH2 CH3 ethoxyethane Substitutive IUPAC Names of Ethers name as alkoxy derivatives of alkanes

  4. CH3OCH2 CH3 CH3CH2OCH2CH2CH2Cl ethylmethyl ether 3-chloropropylethyl ether CH3CH2OCH2 CH3 diethyl ether Functional Class IUPAC Names of Ethers name the groups attached to oxygen in alphabetical order as separate words; "ether" is last word

  5. CH3SCH2 CH3 SCH3 methylthioethane CH3CH2SCH2 CH3 ethylthioethane Substitutive IUPAC Names of Ethers name as alkylthio derivatives of alkanes (methylthio)cyclopentane

  6. CH3SCH2 CH3 SCH3 ethyl methyl sulfide CH3CH2SCH2 CH3 diethyl sulfide Functional Class IUPAC Names of Sulfides analogous to ethers, but replace “ether” as lastword in the name by “sulfide.” cyclopentyl methyl sulfide

  7. Names of Cyclic Ethers O O O Oxirane(Ethylene oxide) Oxolane(tetrahydrofuran) Oxetane O O O 1,4-Dioxane Oxane(tetrahydropyran)

  8. Names of Cyclic Sulfides S S S Thiirane Thiolane Thietane S Thiane

  9. 16.2Structure and BondinginEthers and Epoxides bent geometry at oxygen analogousto water and alcohols

  10. O C(CH3)3 (CH3)3C Bond angles at oxygen are sensitiveto steric effects O O H H CH3 H 105° 108.5° O CH3 CH3 112° 132°

  11. An oxygen atom affects geometry in much thesame way as a CH2 group most stable conformation of diethyl etherresembles pentane

  12. An oxygen atom affects geometry in much thesame way as a CH2 group most stable conformation of tetrahydropyranresembles cyclohexane

  13. 16.3Physical Properties of Ethers

  14. Ethers resemble alkanes more than alcoholswith respect to boiling point boiling point Intermolecular hydrogenbonding possible in alcohols; not possible in alkanes or ethers. 36°C 35°C O 117°C OH

  15. Ethers resemble alcohols more than alkaneswith respect to solubility in water solubility in water (g/100 mL) Hydrogen bonding towater possible for ethersand alcohols; not possible for alkanes. very small 7.5 O 9 OH

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