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