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

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

3. Dr. Wolf's CHM 201 & 202 16-3 name as alkoxy derivatives of alkanes CH 3 OCH 2 CH 3 methoxyethane CH 3 CH 2 OCH 2 CH 3 ethoxyethane CH 3 CH 2 OCH 2 CH 2 CH 2 Cl 1-chloro-3-ethoxypropane Substitutive IUPAC Names of Ethers

4. Dr. Wolf's CHM 201 & 202 16-4 name the groups attached to oxygen in alphabetical order as separate words; "ether" is last word CH 3 OCH 2 CH 3 ethyl methyl ether CH 3 CH 2 OCH 2 CH 3 diethyl ether CH 3 CH 2 OCH 2 CH 2 CH 2 Cl 3-chloropropyl ethyl ether Functional Class IUPAC Names of Ethers

5. Dr. Wolf's CHM 201 & 202 16-5 name as alkylthio derivatives of alkanes CH 3 SCH 2 CH 3 methylthioethane CH 3 CH 2 SCH 2 CH 3 ethylthioethane (methylthio)cyclopentane Substitutive IUPAC Names of Sulfides SCH 3

6. Dr. Wolf's CHM 201 & 202 16-6 cyclopentyl methyl sulfide analogous to ethers, but replace “ether” as last word in the name by “sulfide.” CH 3 SCH 2 CH 3 ethyl methyl sulfide CH 3 CH 2 SCH 2 CH 3 diethyl sulfide Functional Class IUPAC Names of Sulfides SCH 3

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

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

9. Dr. Wolf's CHM 201 & 202 16-9 bent geometry at oxygen analogous to water and alcohols, i.e. sp 3 hybidization 16.2 Structure and Bonding in Ethers and Epoxides

10. Dr. Wolf's CHM 201 & 202 16-10 112° H O H 105° 108.5° (CH 3 ) 3 C O C(CH 3 ) 3 132° H O CH 3 O Bond angles at oxygen are sensitive to steric effects

11. Dr. Wolf's CHM 201 & 202 16-11 most stable conformation of diethyl ether resembles pentane An oxygen atom affects geometry in much the same way as a CH 2 group

12. Dr. Wolf's CHM 201 & 202 16-12 most stable conformation of tetrahydropyran resembles cyclohexane An oxygen atom affects geometry in much the same way as a CH 2 group

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

14. Dr. Wolf's CHM 201 & 202 16-14 boiling point 36°C 35°C 117°C Ethers resemble alkanes more than alcohols with respect to boiling point O OH Intermolecular hydrogen bonding possible in alcohols; not possible in alkanes or ethers.

15. Dr. Wolf's CHM 201 & 202 16-15 solubility in water (g/100 mL) very small 9 7.5 Ethers resemble alcohols more than alkanes with respect to solubility in water O OH Hydrogen bonding to water possible for ethers and alcohols; not possible for alkanes.