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Chapter 16 Ethers, Epoxides, and Sulfides

Chapter 16 Ethers, Epoxides, and Sulfides. Dr. Wolf's CHM 201 & 202. 16-1. 16.1 Nomenclature of Ethers, Epoxides, and Sulfides. Dr. Wolf's CHM 201 & 202. 16-2. 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.

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Chapter 16 Ethers, Epoxides, and Sulfides

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  1. Chapter 16Ethers, Epoxides, and Sulfides Dr. Wolf's CHM 201 & 202 16-1

  2. 16.1Nomenclature of Ethers, Epoxides, and Sulfides Dr. Wolf's CHM 201 & 202 16-2

  3. CH3OCH2 CH3 CH3CH2OCH2CH2CH2Cl methoxyethane 1-chloro-3-ethoxypropane CH3CH2OCH2 CH3 ethoxyethane Substitutive IUPAC Names of Ethers name as alkoxy derivatives of alkanes Dr. Wolf's CHM 201 & 202 16-3

  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 Dr. Wolf's CHM 201 & 202 16-4

  5. CH3SCH2 CH3 SCH3 methylthioethane CH3CH2SCH2 CH3 ethylthioethane Substitutive IUPAC Names of Sulfides name as alkylthio derivatives of alkanes (methylthio)cyclopentane Dr. Wolf's CHM 201 & 202 16-5

  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 Dr. Wolf's CHM 201 & 202 16-6

  7. Names of Cyclic Ethers O O O Oxirane(Ethylene oxide) Oxolane(tetrahydrofuran) Oxetane O O O 1,4-Dioxane Oxane(tetrahydropyran) Dr. Wolf's CHM 201 & 202 16-7

  8. Names of Cyclic Sulfides S S S Thiirane Thiolane Thietane S Thiane Dr. Wolf's CHM 201 & 202 16-8

  9. 16.2Structure and BondinginEthers and Epoxides bent geometry at oxygen analogousto water and alcohols, i.e.sp3hybidization Dr. Wolf's CHM 201 & 202 16-9

  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° Dr. Wolf's CHM 201 & 202 16-10

  11. An oxygen atom affects geometry in much thesame way as a CH2 group most stable conformation of diethyl etherresembles pentane Dr. Wolf's CHM 201 & 202 16-11

  12. An oxygen atom affects geometry in much thesame way as a CH2 group most stable conformation of tetrahydropyranresembles cyclohexane Dr. Wolf's CHM 201 & 202 16-12

  13. 16.3Physical Properties of Ethers Dr. Wolf's CHM 201 & 202 16-13

  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 Dr. Wolf's CHM 201 & 202 16-14

  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 Dr. Wolf's CHM 201 & 202 16-15

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