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ch12 - Chapter12 Alcoholsfrom CarbonylCompounds...

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Created by Professor William Tam & Dr. Phillis Chang Ch. 12 - 1 Chapter 12 Alcohols from Carbonyl Compounds Oxidation-Reduction &  Organometallic Compounds
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Ch. 12 - 2 O 1. Structure of the Carbonyl Group v Carbonyl compounds O R H Aldehyde Ketone O R R' Carboxylic acid O R OH Ester O R OR' Amide O R N R' R"
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Ch. 12 - 3 v Structure O C ~ 120 o ~ 120 o ~ 120 o Carbonyl carbon:   sp2 hybridized Planar  structure
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Ch. 12 - 4 v Polarization and resonance structure O C O C δ - δ +
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Ch. 12 - 5 1A. Reactions of Carbonyl  Compounds with Nucleophiles v One of the most important reactions of carbonyl compounds is  nucleophilic  addition  to the carbonyl group Nu O C δ - δ + nucleophilic addition O C Nu
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Ch. 12 - 6 v Two important nucleophiles: Hydride ions (from NaB H 4 and LiAl H 4) Carbanions (from  R Li and  R MgX) v Another important reactions: O C R H OH R H H oxidation reduction 1 o  alcohol aldehyde
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Ch. 12 - 7 2. Oxidation-Reduction Reactions in Organic Chemistry v Reduction  of an organic molecule usually  corresponds to increasing its hydrogen  content or decreasing its oxygen content carboxylic acid reduction [H] O R H O R O H aldehyde oxygen content decreases reduction [H] O H R H O R H H hydrogen content decreases
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Ch. 12 - 8 v The opposite reaction of reduction is  oxidation .  Increasing the oxygen content  of on organic molecule or decreasing its hydrogen content is   oxidation OH R H H O R OH O R H [O] R CH 3 [H] [O] [H] [O] [H] lowest oxidation state highest oxidation state
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Ch. 12 - 9 v Oxidation of an organic compound may be more broadly defined as a reaction  that increases its content of any element more electronegative than carbon [O] [H] [O] [H] [O] [H] Ar CH 3 Ar CH 2 Cl Ar CH Cl 2 Ar C Cl 3
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Ch. 12 - 10 2A. Oxidation States in Organic  Chemistry v Rules For each C–H (or C–M) bond   -1 For each C–C bond   0 For each C–Z bond   +1 (where M = electropositive element and is  equivalent to H, e.g. Li, K, etc.; Z =  electronegative heteroatom, e.g. OR, SR,  PR2, halogen, etc.) v Calculate the oxidation state of each carbon  based on the number of bonds it is forming  to atoms more (or less) electronegative than  carbon
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Ch. 12 - 11 v Examples H C H H H (1) Bonds to  C : 4 to H = (- 1) x 4 = - 4 Total = - 4 Oxidation state of  C  =  - 4
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Ch. 12 - 12 v Examples H C H H OH (2) Bonds to  C : 3 to H = - 3 Total = - 2 Oxidation state of  C  =  - 2 1 to  O  = +1
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Ch. 12 - 13 v Examples O C H H (3) Bonds to  C : 2 to H = - 2 Total = 0 Oxidation state of  C  =  0 2 to  O  = +2
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Ch. 12 - 14 v Examples O C H OH (4) Bonds to  C : 1 to H = - 1 Total = +2 Oxidation state of  C  =  +2 3 to  O  = +3
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Ch. 12 - 15 v Overall order O C O H C H H H H C H H OH O C H OH O C H H < < < < - 4 - 2 0 +2 +4 lowest  oxidation state of  carbon highest  oxidation state of  carbon oxidation state
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Ch. 12 - 16
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