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