Koreeda Chap13 - Chem 215-ZL6 HH Wll-Notes Dr Masato...

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, Chem 215-ZL6 HH Wll-Notes - Dr. Masato Koreeda - Page 1 of 13 Date: Febrtary 9,2011 Chapter L3. Alcohols, Diols, and Ethers Overview: Chemistry and reactions of sp3 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 CH3OH (1'-alcohols) IUPAC names Common names methanol methyl alcohol CH3CH2OH ethanol ethyl alcohol pKa-r6-17 cH3cH2cH2oH r-propanol n-propyl arcohol t'c;c.-"rro* 2-methyl-1-propanol isobutyl alcohol H.c' h ,lnl--g-"*ro* 2l.-dimethyl-1-propanol neopentyl alcohol " cHs S_e-condary_alcohols t."-.a-On 2-propanol isopropylalcohol (2'-alcohols) HsC' 'H pKa -17-18 H3C-CH2-C-oH 2-butanol sec-buryl alcohol Hsc'h Te-rtiary alcohols tt"'a.-ol.{ 2-methyl-2-propanol tert-butylalcohol t'';:""Ti' H'c'tH, Phenols(Ph-OH) pKa-10-12 Ethers (R-O-R') CH3CH2-O-CH2CH3 diethYl ether Ph-O-CH=CHz phenyl vinyl ether RO-: alkoxy CH3O- methoxy CH3CH2O- ethoxy ArO-: aryloxy PhO- phenoxy II. Oxidation Oxidation - historical use of the term'. (1) oxide (oxyd/oxyde) - the 'acid' form of an elementt e.8., 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 oxidi ze - to increase the Vo oxygen in a substance (reduction: to reduc e the 7o oxygen) More modern definition: oxidation or oxidize - loss of electrons (coupled with reduction as gain of electrons) Note: The loss of electrons (oxidation) by one atom or compound must be matched by the gain of electrons (reduction) by another.
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Chem 2L5-Zl6 HH W11-Notes - Dr. Masato Koreeda lll. Oxidation state (or number) counting (see: "R-"8 Fr- | o-c c-c t-ttJ -2+2 o o Other examples of oxidation numbers: 1. +1p g+1 *r*6' "reducing agent" 00 H-H +2 .7n _1 Br' -Br _1 An atom with a formal charge: incorporate its charge # to its oxidation number. Namely, if an atom has a +1 charge, add +1 to its oxidation number. Example: For N 3 x (- l) from 3 carbon atoms = -3 I +l from oxygen atom = +1 | overall: -1 +l from the charge = +l J For O -1 from nitrogen atom = -1 I overall: _2 -l from the charge = -l J - Page 2 of 13 Date: February 9,2071 pp 513-4 of the textbook) Therefore, ),P H H-C-OH 'lH HH 'u' "oxidizing agent" 00 Br-Br -1 -1 Br Br H-I-LH (9 2.000 Zn + Br-Br oo de Hydrocarbon oxidation-reduction spectrum: "reduction" (hydrogenation) U,@ tt / t/ H-c-H + I H methane u,@ 'i/ H-C-OH I H methanol H c HO o + C=O / HO O=C=O + Hzo \/ "oxidation" (oxygen insertion) \_-/ "oxidation" formaldehyde (methanal) formic acid carbonic acid (methanoic acid) ( also : dehy dr o g enation ) increasing VoO; decreasing VoH "oxidation" decreasing VoO ; increasing VoH ---) "red uction" note: used in biochem.: oxidase = dehydrogenase enzyme
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Chem 215-ZL6 HH W11-Notes - Dr. Masato Koreeda - Page IV. Oxidation
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Koreeda Chap13 - Chem 215-ZL6 HH Wll-Notes Dr Masato...

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