215-216 HH W10 notes-Ch 13-2-5-10

215-216 HH W10 notes-Ch 13-2-5-10 - Chem 215-216 HH W10...

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Chem 215-216 HH W10 Notes – Dr. Masato Koreeda - Page 1 of 12 Date: February 5, 2010 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 ArO-: 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; e.g., 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” (4) oxidation or oxidize – to increase the % oxygen in a substance (reduction: to reduce the % oxygen) More modern definition : oxidation or oxidize – loss of electrons (coupled with reduction as gain of electrons) Note: The loss of electron (oxidation) by one atom or compound must be matched by the gain of electrons (reduction) by another.
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Chem 215-216 HH W10 Notes – Dr. Masato Koreeda - Page 2 of 12 Date: February 5, 2010 III . Oxidation state ( or number) counting (see Ege’s, pp 513-514) eP eN C H -1 +1 O C -2 +2 C C 0 0 "the contribution of an H to the oxidation number of the C is -1" "the contribution of a C to the oxidation number of the H is +1" C H H H H The oxidation number of this C is -4. C OH H H H -2 H C H O 0 Therefore, H H Other examples of oxidation numbers: H H H H H H Br Br H H Br Br -1 -1 0 0 -1 -1 -2 -2 0 0 0 0 +1 +1 +1 +1 "reducing agent" "oxidizing agent" 1. 2. Zn + Br Zn Br Br Br 0 0 0 +2 -1 -1 Hydrocarbon oxidation-reduction spectrum: C H H H H C OH H H H -2 H C H O 0 H HO C O HO HO C O -4 +2 +4 +4 methane methanol formaldehyde (methanal) formic acid (methanoic acid) carbonic acid "oxidation" (oxygen insertion) "oxidation" ( also: dehydrogenation) "reduction" (hydrogenation) O C O + H 2 O increasing %O; decreasing %H "oxidation" decreasing %O; increasing %H "reduction" note: used in biochem.: oxidase = dehydrogenase enzyme
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Chem 215-216 HH W10 Notes – Dr. Masato Koreeda - Page 3 of 12 Date: February 5, 2010 IV. Oxidation of alcohols R C H H O H R C R' H O H R C H O R C O O H R C R' O R C R' R" O H ketone aldehyde carboxylic acid 1°-alcohol 2°-alcohol 3°-alcohol [ox] [ox] - 2H + [ox] - 2H + - H + not easily oxidized Oxidation methods: There are hundreds that differ in experimental conditions, but these follow basically the process shown below.
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This note was uploaded on 02/24/2010 for the course CHEM 215 taught by Professor Koreeda during the Winter '07 term at University of Michigan.

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215-216 HH W10 notes-Ch 13-2-5-10 - Chem 215-216 HH W10...

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