文档介绍：Chapter 14 Ethers, Epoxides, and Sulfides
Jo Blackburn
Richland College, Dallas, TX
Dallas munity College District
ã 2003, Prentice Hall
Organic Chemistry, 5th Edition L. G. Wade, Jr.
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Chapter 14
Introduction
Formula R-O-R where R is alkyl or aryl.
Symmetrical or unsymmetrical
Examples:
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Chapter 14
Structure and Polarity
Bent molecular geometry
Oxygen is sp3 hybridized
Tetrahedral angle
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Chapter 14
Boiling Points
Similar to alkanes parable molecular weight.
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Chapter 14
Hydrogen Bond Acceptor
Ethers cannot H-bond to each other.
In the presence of -OH or -NH (donor), the lone pair of electrons from ether forms a hydrogen bond with the -OH or -NH.
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Solvent Properties
Nonpolar solutes dissolve better in ether than in alcohol.
Ether has large dipole moment, so polar solutes also dissolve.
Ethers solvate cations.
Ethers do not react with strong bases.
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Chapter 14
plexes
Grignard reagents
Electrophiles
Crown ethers
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Chapter 14
Common Names of Ethers
Alkyl alkyl ether
Current rule: alphabetical order
Old rule: order of plexity
Symmetrical: use dialkyl, or just alkyl.
Examples:
diethyl ether or
ethyl ether
t-butyl methyl ether or
methyl t-butyl ether =>
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Chapter 14
IUPAC Names
Alkoxy alkane
Examples:
2-methyl-2-methoxypropane
Methoxycyclohexane =>
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Chapter 14
Cyclic Ethers
Heterocyclic: oxygen is in ring.
Epoxides (oxiranes)
Oxetanes
Furans (Oxolanes )
Pyrans (Oxanes )
Dioxanes
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Chapter 14