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Chapter 10

Chapter 10. Reactions of Alcohols, Amines, Ethers, Epoxides, and Sulfur-Containing Compounds • Organometallic Compounds. An alcohol has a strongly basic leaving group that cannot be displaced by a nucleophile. Mechanism for the S N 1 reaction of an alcohol.

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Chapter 10

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  1. Chapter 10 Reactions of Alcohols, Amines, Ethers, Epoxides, and Sulfur-Containing Compounds • Organometallic Compounds

  2. An alcohol has a strongly basic leaving group that cannot be displaced by a nucleophile

  3. Mechanism for the SN1 reaction of an alcohol

  4. Tertiary alcohols react faster than secondary alcohols in substitution reactions

  5. the SN2 reaction is slower because chloride ion is a poorer nucleophile

  6. Pyridine is used as a base and solvent

  7. Reaction of an alcohol to a sulfonate ester A sulfonic acid has a pKa of –6.5

  8. Sulfonyl chlorides TsCl MsCl TfCl

  9. Elimination Reaction of Alcohols

  10. Dehydration of tertiary alcohols to form alkenes

  11. E2 dehydration and competing SN2 reaction

  12. Dehydration of butanol

  13. Propose a mechanism

  14. Oxidation of Alcohols Oxidation of secondary alcohols to ketones

  15. Oxidation of primary alcohols to carboxylic acids.

  16. 1-Butanol is oxidized to butanal with pyridinium chlorochromate

  17. Mechanism for alcohol oxidation by chromic acid

  18. Relative reactivities of functional groups toward Substitution or Elimination

  19. Nucleophilic Substitution Reactions of Ethers

  20. Ether cleavage: an SN1 reaction

  21. Ether cleavage: an SN2 reaction

  22. Nucleophilic Substitution Reactions of Epoxides

  23. Relative reactivity of ethylene oxide and diethyl ether

  24. Arene Oxides

  25. Phenylalanine Tryptophan

  26. Mechanism for arene oxide rearrangements

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