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60 Cards in this Set
- Front
- Back
- 3rd side (hint)
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Borohydride Ketone Reduction (20.4): Can attack aldehydes and ketones |
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Nucleophilic Acyl Substitution (20.7): RCOCl → RCH₂OH R₂CO→R₂CHOH |
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Organometallic Reduction (20.7) Alum. Hydride Carboxyl Reduction (20.7) |
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Alum. Hydride Amine Reduction (20.7) |
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DIBAL-H Reduction: Use to reduce esters Must be run at -78°C |
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"Lithium tri-tert-butoxyaluminum hydride" Reduction |
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High-Pressure Catalytic Metal Reduction (20.4C) |
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Standard-Pressure Catalytic Metal Reduction (20.4C) |
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Cr⁶⁺ Oxidation of Aldehydes (20.8): Oxidizes alcohols similiarly |
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Cr⁶⁺ Oxidation of Alcohols (12.12)
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Tollens Reagent (20.8): Oxidation of aldehydes No mechanism Selectively oxidize aldehyde to carboxylic acid |
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Enantioselective Carbonyl Reduction (20.6): |
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Enantioselective Carbonyl Reduction (20.6): |
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Deprotanation Grignard (20.9) |
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Organometallic new C-C bond (20.10) |
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Organocuprate Synthesis (20.9) |
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Gignard Reagent Synthesis (20.9) |
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Organolithium Synthesis (20.9) |
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Protection (20.12): tert-butyldimethylsilyl |
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TBAF Deprotection (20.12): Tetra-n-butylammonium fluoride |
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Organometallic Dialkylation (20.13) Acid Halide |
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Grignard Nuceophilic Acyl Substitution (20.13): MUST use (2 equiv.) |
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Carboxylation (20.14) |
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Expoxide Opening (20.14) |
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1,2-Addition Grignard (20.15) |
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1,4-Addition Organocuprate (20.15): Uses Enolate path Organocuprates add 1,4 |
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Alkyne Hydration (11.9) |
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Cyanohydrin Formation (21.9) |
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Cyanohydrin Revertion (21.9) |
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Wittig Formation (21.10): Z isomer (standard) |
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Wittig Formation (21.10): E Isomer (conjugated) CAREFUL: Make sure there are no unprotected alcohols or carboxy groups on your wittig! |
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Wittig Reaction (21.10): [1] Ylide attacks carbonyl Oxaphosphetane Inter. Forming a 1° halide is easier than forming a 2° Adds Z unless the product is conjugated than it forms E |
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Imine Formation (21.11): Formed from 1° amine Carbinolamine interm. Iminium Ion interm. Also called a Schiff base Requires pH 4-5 Every step is in equilibrium |
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Formation of Enamines (21.12): Formed from 2° amine Forms E and Z isomers |
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Enamine Hydrolysis (20.12) |
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Imine Hydrolysis (20.12) |
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Dioxalane Protection (21.14): Carbonyl protection Hemiacetal formation Only occurs with ketones and aldehydes |
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Acetal Formation (21.14): Also with aldehydes Reversible |
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Hydrolysis (21.14): Le Chatelier's Principle Requires a strong acid Carbonyl deprotection Reversible |
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Intramolecular Hemiacetal Formation (21.16): Faster than intermolecular rxns. Cyclic 5 or 6 carbon rings Axial and equatorial isomers Requires aldehydes Reversible |
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Hemiacetal to Acetals (21.16) Reversible |
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Oxidation |
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Anhydride Amidification (22.9) |
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Acid Chloride Hydrolysis (22.8) |
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Acid Chloride Amidification (22.8): Also works with alcohols |
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Thionyl Chloride as Nu (22.10): Pyridine deprotonates NR with anhydrides |
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Intramolecular Anhydride Formation (22.10B) |
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Fischer Esterification (22.10C): Will not work in the presence of a base (forms carboxylate anion) Use strong acid |
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Intramolecular Esterification (22.10C) |
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Acidic Ester Hydrolysis (22.11) |
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Saponification (22.11): Basic ester hydrolysis Resonance-stabilized carboxylate anion Protonate with Strong HA Not reversible |
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Base-Catalyzed Amide Hydrolysis (22.13): Not reversible |
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Acid-Catalyzed Amide Hydrolysis (22.13) |
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Cyano Reduction (22.18) |
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Hindered Cyano Reduction (22.18) |
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Cyano Gringard Rxn. (22.18) Only adds 1 methyl |
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Acidic Cyanohydrin Hydrolysis (21.9) |
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Basic Cyano Hydrolysis (21.9): [2] Imidic Acid [3-4] Tautomerization to Amide [2] Amide hydrolysis |
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IR Absorption: Acid Chloride Anhydride Ester Amide |
1800 cm⁻¹ 1820-1760 cm⁻¹ 1735-1745 cm⁻¹ 1630-1680 cm⁻¹ |
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H NMR Absorptions: Amide N-H Carbonyl Alpha C-H |
7.8-8.5 ppm 2-2.5 ppm |
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