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22 Cards in this Set
- Front
- Back
- 3rd side (hint)
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Catalytic Hydrogenation: Adds H₂ in a syn fashion Adds from top and bottom Cannot be stopped after 1 equiv. Less subst. C react faster |
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Catalytic Hydrogenation of Alkynes: [1] Adds either syn or anti [2] Reacts to form an alkane |
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Lindler Catalytic Hydrogenation: Stops after 1 equiv. Adds syn forming cis alkane Only reacts with alkynes |
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Metal Reduction of Alkynes: Forms trans alkene Uses SET mech. and radicals Trans-vinyl carbanion interm. Reacts only with alkynes |
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Polar Reduction of Epoxides: Sn2 Mechanism Reactivity: 3°<2°<1° H- attacks less subst. C LiAlH₄ source of H- |
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Polar Reduction of Alkyl Halides: Function: Reduces ketones to secondary alcohol Function: Reduces esters to primary alcohols Sn2 Mechanism LiAlH₄ source of H- Reacts w/ alkyl halides and epoxides |
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Metal Hydride Reduction (12.2):Function: Reduces carbonyls to alcoholsSource of H-Polar metal H-bond |
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Radical HBr Addition: Br adds to less subst. C Via radical intermediate Both propagation steps are exo. |
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Epoxidation: Use a peroxyacid, mCPBA Concerted addition Cleavage of the weak O-O bond |
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Anti Dihydroxylation: Forms enantiomer trans-1,2-diols [1] Epoxidation [2] Ring opening Backside attack of C-O bond Anti-addition of two OH groups |
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Syn Dihydroxylation: Cis-1,2-diol Syn addition Limited by organic solvency Reacts under OH- basic conditions |
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Syn Dihydroxylation: Cis-1,2-diol Syn addition Use with NMO to maximize yield |
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Oxidative Cleavage of Alkenes: Yields aldehydes and ketones O₃ Cleavage is called ozonolysis |
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Oxidative Cleavage of Alkynes: Internal alkyne→ carboxylic acidTerminal alkyne→ carboxylic acid and CO₂ |
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Oxidation of 2° Alcohols: 2° alcohols form ketones Cr⁶⁺→ Cr⁴⁺ [1] Formation of chromate ester [2] Loss of a proton |
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Oxidation of 1° Alcohols: PCC yields aldehydes |
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Oxidation of 1° Alcohols: [1] Oxidation to an aldehyde [2] H₂O to form a hydrate [3] Oxidation to carboxylic acid Cr⁶⁺→ Cr⁴⁺ |
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Sharpless Epoxidation: (+)-DET adds O below the plane Asymmetric reaction Only reacts w/ allylic alcohols Transition states are diastereomers |
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Sharpless Epoxidation: (-)-DET adds O above the plane Asymmetric reaction Only reacts w/ allylic alcohols Transition states are diastereomers |
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Radical Halogenation: [1] Initiation [2]Exothermic propagation Resembles reactants [3] Termination |
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Allylic Bromination: Resonance weakens Allylic C-H NBS as source of Br radical Br₂+ CCl₄→ dibromo addition NBS + hv→ allylic subst. ³ |
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HBr Addition: H bonds to less subst. C Via carbocation intermediate |
