1 / 15

Chapter 14 Ethers, Epoxides, and Sulfides

Organic Chemistry , 6 th Edition L. G. Wade, Jr. Chapter 14 Ethers, Epoxides, and Sulfides. =>. Introduction. Formula R-O-R ¢ where R and R ¢ are alkyl or aryl. Symmetrical or unsymmetrical Examples:. =>. Structure and Polarity. Bent molecular geometry Oxygen is sp 3 hybridized

lorin
Download Presentation

Chapter 14 Ethers, Epoxides, and Sulfides

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. Organic Chemistry, 6th EditionL. G. Wade, Jr. Chapter 14 Ethers, Epoxides, and Sulfides

  2. => Introduction • Formula R-O-R¢ where R and R¢ are alkyl or aryl. • Symmetrical or unsymmetrical • Examples: Chapter 14

  3. => Structure and Polarity • Bent molecular geometry • Oxygen is sp3 hybridized • Tetrahedral angle Chapter 14

  4. Boiling Points Similar to alkanes of comparable molecular weight. => 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. 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. Chapter 14

  7. => Ether Complexes • Grignard reagents • Electrophiles • Crown ethers Chapter 14

  8. diethyl ether or ethyl ether t-butyl methyl ether or methyl t-butyl ether => Common Names of Ethers • Alkyl alkyl ether • Current rule: alphabetical order • Old rule: order of increasing complexity • Symmetrical: use dialkyl, or just alkyl. • Examples: Chapter 14

  9. IUPAC Names • Alkoxy alkane • Examples: 2-methyl-2-methoxypropane Methoxycyclohexane => Chapter 14

  10. => Williamson Synthesis • Alkoxide ion + 1 alkyl bromide (or tosylate) • Example: Chapter 14

  11. => Phenyl Ethers • Phenoxide ions are easily produced for use in the Williamson synthesis. • Phenyl halides or tosylates cannot be used in this synthesis method. Chapter 14

  12. Cleavage of Ethers • Ethers are unreactive toward base, but protonated ethers can undergo substitution reactions with strong acids. • Alcohol leaving group is replaced by a halide. • Reactivity: HI > HBr >> HCl => Chapter 14

  13. Mechanism for Cleavage • Ether is protonated. • Alcohol leaves as halide attacks. • Alcohol is protonated, halide attacks, and another molecule of alkyl bromide is formed. => Chapter 14

  14. => Phenyl Ether Cleavage • Phenol cannot react further to become halide. • Example: Chapter 14

  15. End of Chapter 14 Chapter 14

More Related