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Alcohols, Amines, Ethers and Epoxides: Chapter 10. Contents of Chapter 10. Naming Alcohols Substitution and Dehydration of Alcohols Oxidation of Alcohols Naming Ethers Epoxides. Naming Alcohols. Find longest carbon chain containing the alcohol.
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Contents of Chapter 10 • Naming Alcohols • Substitution and Dehydration of Alcohols • Oxidation of Alcohols • Naming Ethers • Epoxides Chapter 10
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
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
Examples Chapter 10
Conversion of Alcohols to Alkyl Halides • Hydrogen halide reactions can be SN1 or SN2 Chapter 10
Mechanism of Substitution Secondary and tertiary alcohols undergo SN1 reaction. Chapter 10
Attack from back-side Mechanism of Substitution Primary alcohols undergo SN2 reaction. Primary carbocations are too unstable to be formed. Chapter 10
Dehydration of Alcohols Zaitsev’s Rule is followed whenever possible Chapter 10
Dehydration of Alcohols Chapter 10
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
Cr6+ Oxidation of Alcohols Chapter 10
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
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
Epoxides Chapter 10