ch12.pptx - Created by Professor William Tam &...

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Unformatted text preview: Created by Professor William Tam & Dr. Phillis Chang Ch. 12 - 1 Chapter 12 Alcohols from Carbonyl Compounds Oxidation-Reduction & Organometallic Compounds 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" Ch. 12 - 3 v Structure O C ~ 120 o ~ 120 o ~ 120 o Carbonyl carbon: sp2 hybridized Planar structure Ch. 12 - 4 v Polarization and resonance structure O C O C - + 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 - + nucleophilic addition O C Nu 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 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 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 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 Ch. 12 - 10 2A. Oxidation States in Organic Chemistry v Rules For each CH (or CM) bond ð -1 For each CC bond ð 0 For each CZ bond ð +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 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 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 Ch. 12 - 13 v Examples O C H H (3) Bonds to C : 2 to H = - 2 Total = 0 Oxidation state of C = 2 to O = +2 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 Ch. 12 - 15Ch....
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This note was uploaded on 01/16/2012 for the course PSYCH 373 taught by Professor Marthafaircloth during the Spring '09 term at Campbell.

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ch12.pptx - Created by Professor William Tam &...

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