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;
49 Cards in this Set
- Front
- Back
|
Eliminating C=C double triple bonds |
H² Metal Catalyst |
|
|
Alkyne to cis alkene |
Lindar catalyst |
|
|
Alkyne to trans alkene |
Birch reduction |
|
|
Keytone to alcohol (+1 substituent) |
Gringard Reagent |
|
|
Synthesize Gringard Reagents |
Magnesium + alkyl halide in ether |
|
|
Ester to tertiary alcohol |
2 Gringard/ether then aqueous |
|
|
Epoxide opening to alcohol |
Gringard rxn (least stericly hindered) |
|
|
Sn2 double bonds/ R group epoxide transfer |
Cuprate (R²CuLi) |
|
|
Reduction of carbonyls/esters |
NaBH⁴ or LiAlH⁴ (for esters |
|
|
Oxidation of alcohols |
PCC, Jones, K²Cr²O7 / H² SO⁴ , Dess Martin |
|
|
Primary Alcohol to Carboxylic Acid |
Jones |
|
|
Alcohol Leaving Group for Sn1 or Sn2 |
Acidify or PBr³ |
|
|
Carboxylic to Ester |
HCl and Primary Alcohol |
|
|
Cleavage of Diols |
IO⁴ |
|
|
Pinacol Rearrangment |
Alcohol acidified, 1-2 methyl shift on carbocation, Alcohol deprotenated for collapse in carbonyl |
|
|
Double bond to epoxide |
m-CPBA (peracid) |
|
|
Epoxide to diol |
Acid and water |
|
|
Splitting C=C bond for two carbonyls |
Ozone + MeS |
|
|
Anti markovnikov addition |
Nuclephile radicalized by peroxide |
|
|
Single bromine addition/ Sn2 |
NBS and UV |
|
|
Diers Alder |
S-cis conjugated alkene and alkene or alkyne with EWG para favored |
|
|
SeA |
Electophile hits double bond and base hits proton (directing effects) |
|
|
Chlorination SeA |
Cl² + AlCl³ |
|
|
Bromination SeA |
Br² FeBr³ |
|
|
Iodination |
I² + HNO³ |
|
|
Sulfination |
SO³ H²SO⁴ |
|
|
Nitration |
HNO³ + H²SO4 (NO²) |
|
|
Adding Alkyls to Aromatics |
Carbocation alkyl and base (AlCl³ Cl/ OH Acid) |
|
|
Adding acyls to aromatics |
Acyl carbocation and base |
|
|
SnAr |
Nu at Halide and adjacent EWG |
|
|
Adding nuclephile to aromatic |
Base and nucleophile |
|
|
Aromatic additon |
H² metal and 1000psi |
|
|
Directing Effects Aromatic |
O,p has line pair for ressonance and activate M doesn't and deactivate Halides o,p but deactivate |
|
|
Reduction to 1,4 cyclohexadienes |
Treat with Na in NH3 Substituent as EWG to make parallel As EDG to make diagnol |
|
|
Keytone into 3° alcohol |
Anionic nucleophile/gringard |
|
|
Immine creation |
Acid catalyzed keytone with 1° amine (Reversible with water) |
|
|
Keytal creation |
Alcohol or R³SH with acid on keytone (Reversible with water) |
|
|
Deoxygenation (removal) of keytone |
HS(CH²)³HS + Acid and RaNi H²NNHTs p-TosH and NaBH³CN |
|
|
Adding R²N groups to keytones |
NR² and acid Creates a double bond by removing a neighboring proton on near carbon |
|
|
Hydration of alkyne to aldehyde |
(Sia)²BH and H²O² |
|
|
Formation of any keytone from formaldehyde |
Thioacytal creation to nBu-Li reacting with 2 1° halides and reversing with water+acid |
|
|
Carboxylic acids to keytones |
Alkyllithiums |
|
|
Nitrilea to keytones |
Gringard with water and acid |
|
|
Acylchlorides to aldehydes |
LiAlH(O-t-Bu)³ |
|
|
Esters to aldehydes |
DIBAL AlH(i-Bu)² |
|
|
Acylchlorides to keytones |
Cuprates R²CuLi |
|
|
Eliminating carbonyls and C-C bind forming |
Ph³P=CH² or CHR (Witting) Cis if R is alkane Trans if R is EWG |
|
|
Protecting a diol |
Acid and keytone for keytal Remove with water in acid |
|
|
Protecting individual alcohol |
RSiCl in Et³N Remove with n-Bu⁴NF |
