Chapter 14 handouts

Chapter 14 handouts - Chapter 14 Ethers, Epoxides, and...

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Chapter 14 Ethers, Epoxides, and Sulfides
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Chapter 14 2 Introduction: Ethers • Formula R-O-R where R is alkyl or aryl. • Symmetrical or unsymmetrical • Examples: OC H 3 CH 3 H 3 O
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Chapter 14 3 Structure and Polarity • Bent molecular geometry • Oxygen is ____ hybridized • _____________ angle =>
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Chapter 14 4 Boiling Points Similar to alkanes of comparable molecular weight.
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Chapter 14 5 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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Chapter 14 6 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 7 Ether Complexes • Grignard reagents • Electrophiles • Crown ethers OB H H H + _ BH 3 THF =>
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Chapter 14 8 Common Names of Ethers • Alkyl alkyl ether • Current rule: alphabetical order • Old rule: order of increasing complexity • Symmetrical: use dialkyl, or just alkyl. • Examples: CH 3 2 OC H 2 3 3 3 3 3
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Chapter 14 9 IUPAC Names • Alkoxy alkane (more complex alkane as root) • Examples: CH 3 OC 3 3 3 H 3
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Chapter 14 10 Cyclic Ethers • Heterocyclic: oxygen is in ring.
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This note was uploaded on 04/08/2008 for the course CHEM 223 taught by Professor Pearson during the Fall '07 term at Case Western.

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Chapter 14 handouts - Chapter 14 Ethers, Epoxides, and...

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