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24 Cards in this Set
- Front
- Back
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alkene → haloalkene
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Alkene hydrohalogenation:
Addition of H-X |
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alkene → alcohol
(Markovnikov) |
Acid catalyzed hydration:
Addition of H2SO4 and H2O Markovnikov |
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alkene → vicinal trans dibromide
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Bromination of alkene:
Addition of X2 Anti addition stereoselectivity |
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alkene → alcohol
(anti-Markovnikov) |
Hydroboration-oxidation
Addition of 1. BH3, 2.H2O2, NaOH Anti-Markovnikov regioselectivity Syn stereoselectivity (addition of H and OH) |
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alkene → vicinal diol
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OsO4 oxidation:
Addition of 1. OsO4, 2. NaHSO3, H2O Syn stereoselectivity |
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alkene C=C double bond → two C=O double bonds
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Ozonolysis:
1. O3, 2. (CH3)2S |
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alkene → alkane
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Alkene hydrogenation:
Addition of H2 and Pt Syn stereoselectivity |
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alkene → alkyne
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Alkyne synthesis:
Addition of 1. Br2 and 2. LDA |
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alkyne → dihaloalkane
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Alkene hydrohalogenation:
Addition of HBr twice Markovnikov (regioselective) |
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alkyne → trans alkene
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Dissolving metal reduction:
Addition of 2 Na and NH3 Anti addition of hydrogens Stereoselective |
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alkyne → cis alkene
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Lindlar's catalyst:
Addition of H2 and Lindlar's catalyst Syn stereoselective |
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alkyne → aldehyde
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Addition of:
1. (sia)2BH 2. H2O2 NaOH |
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alkyne → ketone
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Mercury catalyzed hydration:
Addition of H2SO4, HgSO4, H2O =O goes on more hindered side of triple bond |
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alkane → haloalkane
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Bromination of alkane:
Addition of Br2 and hv Regioselective (Markovnikov?) |
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alcohol → halide
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Addition of PBr3
Selective- only one group reacts Br replaces OH on opposite face (inversion of stereochemistry) |
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alcohol → tosylate
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Addition of TsCl and pyradine
OTs replaces OH on same face (no inversion of stereochemistry) |
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diol → ketone
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Pinacol rearrangement:
Addition of H2SO4 and heat Methyl shift in mechanism |
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primary alcohol → carboxylic acid
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Addition of K2Cr2O7; H2SO4, H2O
K2Cr2O7 oxidizes alcohol all the way |
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primary alcohol → aldehyde
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Addition of PCC
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secondary alcohol → ketone
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Addition of K2Cr2O7; H2SO4, H2O
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alcohol → alkene
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Addition of H2SO4 and heat
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alkene → epoxide
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Addition of mCPBA
Stereospecific: trans alkene to trans epoxide, etc. |
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epoxide → trans diol
(most substituted) |
Acid catalyzed epoxide ring opening
Addition of H2SO4 and H2O Backside attack and inversion of stereochemistry at most substituted carbon |
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epoxide → trans diol
(least substituted) |
Nucleophilic epoxide ring opening
Addition of Nuc:-Na+ and CH3OH Backside attack and inversion of stereochemistry at least substituted carbon |
