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Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols Paula Yurkanis Bruice

Chapter 9. Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols Paula Yurkanis Bruice University of California, Santa Barbara. Contents of Chapter 9. Naming Alcohols Substitution and Dehydration of Alcohols Oxidation of Alcohols Naming Ethers Epoxides

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Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols Paula Yurkanis Bruice

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  1. Chapter 9 Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols Paula Yurkanis Bruice University of California, Santa Barbara

  2. Contents of Chapter 9 • Naming Alcohols • Substitution and Dehydration of Alcohols • Oxidation of Alcohols • Naming Ethers • Epoxides • Skip Thiols and SAM Methylation Chapter 10

  3. Naming Alcohols • Find longest carbon chain containing the alcohol. • OH gives attached carbon lowest possible number. • Break ties with other substituents if necessary. • Substituents are listed in alphabetical order. Chapter 10

  4. Examples • Determine longest chain with OH • Blue chain is longer; however, • Red chain contains OH Notice that numbering starts at alcohol group 2. Name: 2-propyl-1-hexanol Chapter 10

  5. Examples Chapter 10

  6. Conversion of Alcohols to Alkyl Halides • Hydrogen halide reactions can be SN1 or SN2 Chapter 10

  7. Mechanism of Substitution Secondary and tertiary alcohols undergo SN1 reaction. Chapter 10

  8. Attack from back-side Mechanism of Substitution Primary alcohols undergo SN2 reaction. Primary carbocations are too unstable to be formed. Chapter 10

  9. Dehydration of Alcohols Zaitsev’s Rule is followed whenever possible Chapter 10

  10. Dehydration of Alcohols Chapter 10

  11. Cr6+ Oxidation of Alcohols Acidic hexavalent chromium removes all  H’s makes C-O bonds PCC removes only one  H and makes an aldehyde from a 10 alcohol Chapter 10

  12. Cr6+ Oxidation of Alcohols Chapter 10

  13. Oxidation by Hypochlorous Acid (HOCl)

  14. methyl isopropyl ether methyl ethyl ether 2-methoxy-butane 1-ethoxy-2-methylpropane Nomenclature of Ethers • Common Name: Name of alkyl substituents followed by “ether” • IUPAC • Parent alkyl compound with RO substituent. “-yl” is then replaced by “oxy” Chapter 10

  15. Substitution Reactions of Ethers • Ethers can be cleaved only with HI and HBr, not HCl • SN1 and SN2 reactions give opposite regioselectivity; H goes on bulky C in SN2, and less-hindered in SN1 Chapter 10

  16. Epoxides Chapter 10

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