1. Chapter 16 Ethers, Epoxides, and Sulfides
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2. 16.1 Nomenclature of Ethers, Epoxides, and Sulfides2

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

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

5. Substitutive IUPAC Names of Sulfides
Name as alkylthio derivatives of alkanes.
CH3SCH2 CH3
SCH3
methylthioethane
(methylthio)cyclopentane
CH3CH2SCH2 CH3
ethylthioethane 3

6. Functional Class IUPAC Names of Sulfides
Analogous to ethers, but replace “ether” as last word in the name by “sulfide.”
CH3SCH2 CH3
SCH3
ethyl methyl sulfide
cyclopentyl methyl sulfide
CH3CH2SCH2 CH3
diethyl sulfide 3

7. Oxirane (Ethylene oxide) Oxetane Oxolane (tetrahydrofuran)
Names of Cyclic Ethers O O O
Oxirane (Ethylene oxide)
Oxetane
Oxolane (tetrahydrofuran)
Oxane (tetrahydropyran)
1,4-Dioxane O O O 3

8. Names of Cyclic Sulfides
Thiirane
Thietane
Thiolane
Thiane S 3

9. 16.2 Structure and Bonding in Ethers and Epoxides
bent geometry at oxygen analogous to water and alcohols 8

10. Bond angles at oxygen are sensitive to steric effectsH H
CH3 H
112°
105°
108.5°
132° O
(CH3)3C O
C(CH3)3
CH3
CH3 9

11. An oxygen atom affects geometry in much the same way as a CH2 group
Most stable conformation of diethyl ether resembles that of pentane. 10

12. An oxygen atom affects geometry in much the same way as a CH2 group
Most stable conformation of tetrahydropyran resembles that of cyclohexane. 10

13. 16.3 Physical Properties of Ethers11

14. Table 16.1 Ethers resemble alkanes more than alcohols with respect to boiling point
Intermolecular hydrogen bonding possible in alcohols; not possible in alkanes or ethers.
36°C
35°C O
117°C OH 12

15. solubility in water (g/100 mL)
Table 16.1 Ethers resemble alcohols more than alkanes with respect to solubility in water
solubility in water (g/100 mL)
very small
7.5
Hydrogen bonding to water possible for ethers and alcohols; not possible for alkanes. O 9 OH 12