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37 Cards in this Set
- Front
- Back
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Hydration of Alkene (Markovnikov)
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Acid Catalyzed (H+)
Oxymercuration/demercuration (1. HgAOC 2. NABH4) |
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Hydration of Alkene (Anti-Markovnikov)
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Hydroboration (BH3+THF)
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H-X Addition to Alkene (Markovnikov)
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H-X
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H-X Addition to Alkene (Anit-Markovnikov)
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ROOR, H-Br, heat
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Add X2 to Alkene
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X2
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Add -X and -OH to alkene
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X2, H2O
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Add -OR and H to double bond
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Alkoxymercuration/demercuration
(1. HgAOC, R-OH 2. NaBH4) |
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Add carbon to form ring at double bond (no halogens)
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Simmons Smith Rxn (CH2I2, Zn, Cu, CL)
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Add carbon to form ring at double bond (halogens too)
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CHBr3, KOH, H2O
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Epoxidation of Alkene
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MCPBA
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Alkene -> Anti-diol
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1. Epoxidation (MCPBA)
2. Cracking of epoxide (H+, H2O) |
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Alkene -> Syn Diol
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OsO4, H2O2
or KMNO4, -OH (cold and dilute) |
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Oxidative Cleavage
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KMNO4 (Warm, concentrated)
O3, DMSO (removes extra O) |
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Make Acetylide Ion
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Primary Alkyne + NaNH2
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Alkylation of Acetylide Ion
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Acetylide Ion + R-X
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Make terminal Alkyne from dibrominated alkane
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Di-brominated alkane + NaNH2
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Make Internal Alkyne from dibrominated alkane
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Di-brominated alkane + Fused KOH
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Anti-hydrogenation of Alkyne
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Na +NH3
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Syn-hydrogenation of Alkyne
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Complete: H2 (Pt)
Partial :H2, Pd, BaSO4, quinoline, CH3OH |
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Add X to Alkyne (E/Z?)
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H-X
If terminal, Markovnikov If not, both products |
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Hydration of Alkyne to Aldehyde/Ketone (Markovnikov)
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Hg2+, H2O, H3O+
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Hydration of Alkyne to Aldehyde/Ketone (anit-Markovnikov)
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HB(Sia)2, H2O2
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Add R group, convert =O to -OH
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Organometallic Reagent
1. R-X+Mg =R-Mg--X 2. R-X +2Li = R-Li +Li+ + X- |
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Reduction, add H (ketone, aldehyde, carb. acid, ester to alcohol)
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Hydrides, (NaBH4 weak, LiAlH4 strong)
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Alkyne to 2 carb acids
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Warm basic KMNO4, O3 + H2O +-OH)
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Oxidation
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+O, O2, X2.
-H2 |
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Reduction
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+H2
-O, O2, X2 |
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Primary alcohol to carb acid
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Jones Reagent (H2CrO4, Acetone, H2O, H2SO4)
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Secondary Alcohol to Ketone/Aldehyde
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Jones Reagent (H2CrO4, Acetone, H2O, H2SO4)
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Primary alcohol to ketone/aldehyde
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PCC, (DMSO/CCOCl)
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R-OH -> R-X
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PBr3, P/I2, SOCl2
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Esterification of Carb Acid and Alcohol
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H+, carb acid, alcohol
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Removes OH group
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1. H2SO4, heat,
H2, Pt 2. TsCl, pyridine, LiAlH4 |
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Acid Cleavage of Ester
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R-O-R +H-X = R-X + R-X + H2O
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Lewis Acid Cleavage
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AlCl3, H3O+
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Epoxide from alkane w/o MCPBA
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X2, H2O
Base (NaOH) |
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Break Epoxide add R group
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Epoxide, Li-R
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