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84 Cards in this Set
- Front
- Back
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Alcohol
Acid + Heat |
Secondary Alkene
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Alcohol
Base + Heat |
Alkene
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Geminal/Vincinal X
Base + Heat |
Alkyne
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Acetyline
n-BuLi |
Nucleophile
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Alkene
H2 + Pd |
Alkane
syn |
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Alkyne
H2 + Pd + quinoline (Lindar's) |
cis-Alkene
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Aromatic
H2/Rh/Pt/Pd + Heat over carbon |
Alkane
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Alkene
HX |
Monosub'd X
Mark |
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Alkene
X2 |
Di-Sub
anti-syn |
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Alkyne
X2 |
Di-sub'd
anti-syn (progresses to 4-sub'd alkane) |
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Alkene
Free Radical |
Eliminates DB
anti-Mark |
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Alkene
H20 + Acid |
Alcohol
Mark |
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Alkene
BH3 + THF H2O2 |
Alcohol
anti-Mark |
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Terminal Alkyne
R2BH + OH H2O2 |
Aldehyde
anti-Mark |
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Alkyne
BH3 + Acetic Acid |
cis-Alkene
anti-Mark |
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Alkyne
Na + NH3 |
trans-Alkene
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Alkene
Cold KMnO4 |
Diol
syn |
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Alkene
Hot KMnO4 + Acid |
Cleaved and fully oxidized to CA
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Alkyne
KMnO4 + OH |
Cleaved and fully oxidized to CA
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Aldehyde
KMnO4/CrO3/Ag2O |
CA
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Alkene
MCPBA |
Epoxide
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Alkene
O3 Zn+H2O |
Cleaved and Aldehydes/Ketones
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Alkyne
O3 Zn+H2O |
Cleaved and oxidized to CAs
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Alcohol
PCC |
Ketone or Aldehyde
PCC is a weak oxidizer |
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Alcohol
Na2Cr2O7/H2SO4 |
Ketone or CA
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Phenol
Na2Cr2O7/H2SO4 |
Quinones (ketone on an aromatic)
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Alcohol
CrO3/H2SO4 Acetone |
Ketone or CA
Jones's Oxidation |
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Aromatic
FeBr2 + Heat |
Monosub'd Br ring
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Aromatic
SO3/H2SO4 + heat |
Monosub'd SO3H ring
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Aromatic
HNO3/H2SO4 |
Monosub'd NO2 ring
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Aromatic
HNO3/H2SO4 H3O+ |
Phenol
Because NO2 is a good leaving group |
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Benzene + Alkyl Halide
AlCl3 |
Monosub'd ring
Friedel-Crafts |
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Benzene + Anhydride
AlCl3 |
Ring with Ketone + R-COO-
FC-Acylation |
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Alcohol
HBr |
sub'd for Br
SN1 |
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Alcohol
Tosyl Chloride NAI |
Sub'd for I
SN2 |
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CA
LiAlH H3O+ |
Alcohol
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Aldehyde
NaBH4 H3O+ |
Alcohol
NABH4 doesn't work on esters, CAs, amides |
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Metal alkoxide + unhindered alkyl C
NaOH |
Ether + NaX
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Phenol + Alkyl X
NaOH |
Ether
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trans 1-OH 2-X
NaOH |
cyclic ether
SN2 |
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Ether + O2 (g)
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Peroxides
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Ether
HBr/HI + heat |
Cleavage into Alcohol and RX
SN1 and SN2 |
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Epoxide
HBr (Acid) |
Br on most sub'd C
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Epoxide
Br- (Base) |
Br on least sub'd C
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Enol + Alkyl X/Alkenes
Strong Base (LDA) |
alpha carbon attacks X or DB
SN2 Michael addition |
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Ketone + Nucleophile
Nu- |
Alcohol attached to nucleophile
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Ketone
HCN |
OH-C-CN
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Ketone
H2O |
OH-C-OH
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Ketone
NH3 |
C=NH2+
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C=O
H2NNH2 Base+ Heat |
C
only if stable when basic, otherwise use Clemmensen |
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C=O
Zn(Hg) + HCl |
C
unrestricted Clemmensen |
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C=O
Phosphonium salt (PH4+) |
C=C
Wittig |
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Aldehyde
RMgBr + H+/Et2O/THF |
Alcohol + R
Grignard |
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C=O
RMgBr + H+/Et2O/THF |
R-C-OH
Grignard |
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Ester
RMgBr + H+/Et2O/THF |
3* OH-C-(R)2
Kills the ester, ejecting the other O and sidechain Grignard |
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Aldehyde + Enol
|
1-al 2-ene
Aldol condensation |
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Amide
H2O |
CA + R-NH2
If there is an R group, otherwise also H |
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Amide
Br2 + NaOH |
Amine
Loses CO2 Hoffman Rearrangement |
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Amide
LAH |
Amine
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Ester
NH3 |
Amide + Alcohol
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R-X
Pthalimide + NaOH |
R-NH2
SN2 |
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NO2
Zn + HCl |
NH2
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Nitrile
LAH |
1* Amine
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Ketone C=O
NH3 + H2 + Raney Nickel |
Amine C-NH2
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Amine C-NH2
CH3-I Ag2O + Heat |
Alkene + N-(CH3)3
DB generated on broken C, anti-Mark Hoffman exhaustive methylation |
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Anhydride
NH3 |
Amide + COO- NH4+
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Anhydride
H2O |
CA + CA
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Anhydride
Alcohol |
CA + Ester
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CA + CA or CA + Alkyl X
heat |
Anhydride
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3* Alkyl X
Mg/Ether Dry Ice/Et20/THF |
3* C-COOH
The only way to attack 3* groups |
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NH3 + Alkyl X
NH3 |
R-CO-NH2
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Alkyl X
LiAl(O-R)3H |
Aldehyde
Bulky group prevents full reduction to alcohol |
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R-X
HCN |
R-CN
SN2 |
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R-CN
H+/H2O |
R-COOH
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Alcohol + CA
Acid |
Ester
Works best with 1* Alcohols, and alcohols can switch the R position |
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Ester
Base |
Alcohol + CA
Saponification |
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Ester
LAH |
2 Alcohols
doesn't work with NaBH4 |
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CA
SOCl2/H2SO4 |
Alkyl Cl
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1,3 DiCAs / beta-keto acides
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Ketone + CO2
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Sugar C1 Aldehyde
Cu(OH)2 |
C1 CA
Benedict's solution, turns red |
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Sugar C1 Aldehyde
Ag+ |
C1 CA
Tollen's Solution, precipitates silver |
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Sugar
KMnO4 |
C1 and C6 CA
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Sugar + Alcohol
HCl |
Attachment of alcohol to C1
alpha or beta glycosidic linkage |
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Sugar + Acid Anhydride
cold pyridine |
Esterification of all OH groups
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