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73 Cards in this Set
- Front
- Back
H-Br
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Markovnikov addition of Br onto more substituted carbon
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H-Br, ROOR, heat
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Anti-Markovnikov addition of Br onto least substituted carbon
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Br2 heat
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Br Addition to more substituted carbon
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Br2, H2O2
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Br addition to least substituted carbon
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H2SO4 (aq)
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Markovnikov addition of OH onto more substituted carbon
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Hg(OAc)2, H2O, NaBH3, -OH
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Markovnikov addition of OH onto more substituted carbon
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1.BH3*THF, THF
2.H2O2, -OH |
Anti-Markovnikov addition of OH onto least substituted carbon
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SN2
NaOH (aq), THF |
Replaces leaving group (Br) with OH
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Aldehyde or Ketone
"R-" or "H-" +work up |
Makes an alcohol from the double bond O. Cant have acidic proton around
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"H-"
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LiAlH4 (LAH)
NaBH4 |
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"R-"
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MgBr-R
Li-R CCR |
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Epoxide to Alcohol
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"R-" or "H-"
+Work Up Opens least substituted carbon |
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R-O-R to Alcohol
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H-X
attacks least substituted carbon except for phenyl or t-Bu |
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Cis Diols
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KMnO4 cold dilute, -OH
OsO4, H2O4 |
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Trans Diols
Epoxide Ring |
NaOH, H2o, H2SO4, H3PO4
Acidic opens more substituted side Basic opens least substituted side |
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Epoxide Ring
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mCPBA, CH2Cl2
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Thionyl Chloride
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SOCl2, Et3N
Replaces OH with Cl |
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PBr3
PI3 |
Replaces OH with halogen
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Sulfonate Ester
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O
Cl-S-R O With double bonds to the O (s) |
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Alkoxymercuration-Demurcuration
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a. Hg(OAc)2, ROH
b. NaBH3 |
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Williamson Ether Synthesis
SN2 |
RO-
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Diol Dehydration
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H2SO4 (aq)
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Thioether
SMe3 |
removes H and adds Methyl group onto O
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Jones Reaction
overoxidizes |
CrO3, H2SO4 (aq), acetone
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DiChromate
overoxidizes |
NaCr2O7, H2SO4 (aq), acetone
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PCC
stops at aldehyde |
PCC (CrO2OHCl)
NaOAc, CH2CL2 no water |
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Allyic or Benzylic
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MnO2 (excess), acetone
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Swern
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1. DMSO (SOMe2), (COCl)2, CH2Cl2, -78^
2.Et3N, -78^ to 0^ |
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RCOOH to Aldehyde or Ketone
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R-Li (2eq), Et2O
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Acetals
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HO__OH, touluene, TsOH (cat)
NO water |
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Remove Acetals
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H2O, H+
Acid |
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ThioAcetals
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HS___SH, ZnCl2, Et2O
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Removal of ThioAcetals
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HgCl2, CaCO3, MeOH/H2O
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Raney Nickel
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H2, Ra-Ni
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Wolff-Kishner Reduction
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1.H2NNH2, TsOH (cat)
2.KOH (aq), heat |
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Clemmensen Reduction
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H-Cl (aq), Fe/Zn, heat
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Umpolung
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ThioAcetal + Li-n-Bu, THF
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Cyanohydrin
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NaCN, TsOH (cat)
Strong Acid H-Cl |
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Wittig Reaction
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Ph3P--CH2, ET2O
*replaces double bond O with double bond attached to P ONLY FORMS Z ORIENTATION |
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Reductive Animation from Ketone or Aldehyde
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NR2H, NaCNBH3, pH 3-4, AcOH
replaces double bond O with NR2 and H |
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SN2 with -CN
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-CN, LAH, Et2O
removes LG adds CH2NH2 H on C from LAH, H on N from w/u |
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SN2 with Amine (NH3, 1, or 2)
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Amine (excess)
Basic Work Up (NaHCO3, H2O) *over alkylizes |
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SN2 with N3
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a.Na-N3, DMF
b.LAH, H2 Pd/C adds NH2 |
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Gabriel Synthesis
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1. cyclohexane with ketones coming off attached to N, DMF
2. KOH, heat *NH2 with work up |
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Oxidation of Amides
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LAH, Et2O
*Keeps NH2, removes ketone |
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Hofmann Rearrangement
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Br2, NaOH
*Removes the carbon with the double bond O from chain |
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Hofmann Elimination
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1.CH3I (excess), K2CO3
2.Ag2O, H2O, heat *removes Amine and forms least substituted alkene |
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Primary Alcohol Oxidation
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Jones or DIChromate
*Forms RCOOH |
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Oxidation Cleavage
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KMnO4 warm concentrated, H+
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R-CN H+, H2O RCOOH
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RCOOH from RCN
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"R-" to RCOOH
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CO2
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RCOOH doesnt react with
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NaBH4 or Acetals
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RCOOH to Acid Chloride
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SOCl2, DMF
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Acid Chloride to RCOOH
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H2O
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Acid Chloride with LAH
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primary alcohol
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Acid Chloride with "R-" (2eq)
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-CR2OH
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Acid Chloride with LiAl(OR)3H
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aldehyde H replaces Cl
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Acid Chloride with R2CuLi
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ketone with R group where the Cl was
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Acid Chloride to Ester
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ROH or RO-
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Acid Chloride to Amide
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Amine (NH3, 1, 2)
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Acid Chloride to Anhydride
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RCOOH
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Anhydride from RCOOH
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heat
-H2O |
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Ester from RCOOH
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Ch3I, Na2CO3
*makes alcohol into methoxy (whatever is attached to the I) |
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Ester from RCOOH (2)
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ROH, TsOH (cat)
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Ester from RCOOH
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CH2N2, Et2O
*makes methoxy |
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Ester to Ester
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ROH, TsOH (cat), heat
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Hydrolysis for Ester
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RCOOR. H2O, -OH or H+
*makes RCOOH and R.OH |
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Amide from Acid Chloride, Anhydride, or Ester
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Amine (NH3, 1, 2)
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Amide from RCOOH
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Amine, heat
-H2O |
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Amide from RCN
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-OH, heat
*RCONH2 |
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Amide with LAH
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removes double bond O
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Amide to RCOOH
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H2O, -Oh or H+, double heat
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Protect Alcohol
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isobutylene, TsOH (cat)
removed with H-X (I) |