215F07-notes-9-12-07 - Chem 215 F07 Notes Dr Masato Koreeda...

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Chem 215 F07 Notes – Dr. Masato Koreeda - Page 1 of 5. Date: September 12, 2007 Chapter 13. Alcohols, Diols, and Ethers Overview : Chemistry and reactions of sp 3 oxygen groups, particularly oxidation of an alcohol, ether formation, and reactions of oxirane (epoxide) groups. I . What are alcohols, phenols, and ethers? Alcohols (R-OH) Primary alcohols (1°-alcohols) CH 3 OH methanol methyl alcohol CH 3 CH 2 OH ethanol ethyl alcohol CH 3 CH 2 CH 2 OH 1-propanol n -propyl alcohol pKa ~16-17 H 3 C C CH 2 OH H 3 C H 2-methyl-1-propanol isobutyl alcohol H 3 C C CH 2 OH H 3 C CH 3 2,2-dimethyl-1-propanol neopentyl alcohol H 3 C C OH H 3 C H Secondary alcohols (2°-alcohols) pKa ~17-18 2-propanol isopropyl alcohol H 3 C-CH 2 C OH H 3 C H 2-butanol sec -butyl alcohol H 3 C C OH H 3 C CH 3 Tertiary alcohols (3°-alcohols) pKa ~19 2-methyl-2-propanol tert -butyl alcohol Phenols (Ph-OH) pKa ~10-12 Ethers (R-O-R') CH 3 CH 2 -O-CH 2 CH 3 diethyl ether Ph-O-CH=CH 2 phenyl vinyl ether RO-: alkoxy methoxy ethoxy PhO-: aryloxy phenoxy CH 3 CH 2 O CH 3 O PhO I U P A C n a m e s C o m m o n n a m e s II. Oxidation Oxidation – historical use of the term : (1) oxide (oxyd/oxyde) – the ‘acid’ form of an element S + air oxide of S (acid of sulfur) (2) oxidation or oxidize – to make such an acid, to make the oxide (3) oxygen – Lavoisier: substance in the air that makes acids “the bringer of acids” = “oxygen”
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