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Overview of Ethers and Alkoxides: Structures, Reactions, and Synthesis

This document provides a comprehensive overview of ethers and alkoxides, two important classes of organic compounds. It covers the structure and general properties of common ethers like diethyl ether and ethylmethyl ether, as well as heterocyclic ethers such as furan and tetrahydrofuran. Detailed descriptions of the synthesis methods for alkoxides and ethers are included, along with specific reaction examples. Additionally, the document includes exercises for predicting and naming organic products from dehydration reactions and alkoxide formations.

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Overview of Ethers and Alkoxides: Structures, Reactions, and Synthesis

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  1. Drill: Draw: 2-amino-4-hydroxybutanoic acid

  2. Ether • R1-O-R2 • CH3-CH2-O-CH3 • Ethylmethyl ether

  3. Common Ethers • CH3-CH2-O-CH2-CH3 • Diethyl ether • General anesthetic

  4. Common Ethers • Diphenyl ether O

  5. Heterocyclic Ethers

  6. Heterocyclic • A carbon ring structure with an element other than carbon in the ring

  7. Furan O

  8. Tetrahydrofuran O

  9. Pyran

  10. Tetrahydropyran

  11. Epoxide • O • C C

  12. Epoxyethane • O • H2C CH2

  13. Epoxide Addition Reaction • O • C C + H-O-H • HO OH • -C C- HCl hydration

  14. Epoxide Reaction • O H2C CH-CH3+H2O HCl

  15. 1,2-Propanediol • HO OH • H2C CH-CH3

  16. HO O cannabinol

  17. HO O tetrahydrocannabinol

  18. Drill: Draw the reactants, then predict, draw, & name the major organic products in the dehydration of2-pentanol.

  19. Alkoxides Similar to hydroxides, but with an alkane H-O- R-O-

  20. Alkoxides Alkoxides are used to make ethers

  21. Making Alkoxides • Add an alkali metal to an alcohol • Alkoxide: R-O-

  22. Alkali + Water • H-O-H + M • M+ + H-O- + H2

  23. Making Alkoxides • R-OH + M • M+ + R-O- + H2

  24. Alkoxide Example • -OH + K

  25. Alkoxide Example -O- + K+ + H2

  26. Making Ethers • Alkoxides + alkyl halides • R1-O- + R2-X • R1-O-R2 + X-

  27. Making Ethers • CH3-CH2-O- + CH3-I • CH3-CH2-O-CH3 + I-

  28. Predict & Name Products • CH3-CH2-O- • + CH3-CH2-I

  29. Organic HWPredict & draw theorganic products • F-CH2-CH2-CH2-CH2-O-

  30. Making Ethers • F-CH2-CH2-CH2-CH2-O- O + F-

  31. Organic Quiz:Name reactant, then Predict & draw theorganic products • I-(CH2)5-O-

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