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;
45 Cards in this Set
- Front
- Back
|
Alkyne-> Aldehyde
|
hydroboration, BH3/TH__H2O2/OH
enol -> aldehyde |
|
|
Alkyne -> trans alkene
|
Na(s) ___ NH3 (l) uses free electrons
|
|
|
Alkyne -> alkane
|
H2__Pd/C for alkane
|
|
|
Alkyne -> cis alkene
|
H2__Pd/C and LIndlar poison such as Pb(OAc)2
|
|
|
Alkyne -> Alkyne
|
strong base such as LDA/n butyl Li
and primary alkyle bromide. attacks with carbanion |
|
|
Alkyne -> alkene with Br
|
Br2 __ CH2Cl2 trans Br
|
|
|
Ketone -> Alkyne
|
PCl5 to geminal dicholoride with NaNH2 __NH3 to alkyne
|
|
|
Alkene -> Alkyne
|
Br2__CH2Cl2 to alkyl halide with LDA to alkyne. no stereochemistry
|
|
|
Alcohol -> alkene
|
H3O+ E1 elimination doesn't occur with primary alcohol
|
|
|
1 Alcohol to Aldehyde
|
Pyridinium chlorochromate__CH2Cl2
|
|
|
2 or 3 alcohol to alkene
|
E2 elimination with sulfonate elster as LG
|
|
|
Alkene -> Alcohol
|
Br2 forms more substituted alcohol.
may also form vicinal dibromide |
|
|
Alkene -> Alcohol
(Anti-markovnikov) |
1. BH3/THF
2. H2O2/OH- gives less substituted alcohol |
|
|
Epoxide ring opening
|
epoxide + HBr__CH2Cl2.
Br attacks less substituted ring |
|
|
Alkene -> alcohol
(markovnikov) |
oxymercuration
|
|
|
Alkoxides
|
Alcohol + NaH
|
|
|
Epoxide -> Amine
|
1. epoxide and NaN3
2. acid workup 3. H2.Pd/C |
|
|
Halogen -> Amine
|
1. alkyl halide + NaN3
2. acid workup 3. H2 Pd/C |
|
|
1 Alcohol -> Aldehyde
|
PCC__CH2Cl2
|
|
|
Alcohol protection
|
Benzyl ether. 1. NaH 2. BnBr
(whatever reaction you actually want to do) 3. H2__Pd/C |
|
|
Alkyne -> Ketone/aldehyde
|
1. H3O+
|
|
|
C--C bond formation
|
!. alkyl Li. Li__hexane with alklyl Br
|
|
|
1 Alcohol -> Carboxylic acid
|
1. KMnO4 2. HCl
|
|
|
1 or 2 Alcohol -> aldehyde, ketone
|
1. Na2CrO4__H2SO4/H3O+
|
|
|
Alkene -> aldehyde, ketone
|
O3__(CH3)2S
|
|
|
glycol -> aldehyde/ketone
|
HIO4__H2O
|
|
|
Epoxide ring opening
|
Li organocuprates__hexane.
not effective with complex epoxides |
|
|
1 Alcohol -> carboxylic acid
|
K2Cr2O7___aqueous H2SO4
|
|
|
alkyl bromide -> C----C bond formation
|
alkyl bromide + Mg___THF or ether
|
|
|
1 alcohol -> ether
|
2 primary alcohols + strong acid (dehydration) good for symmetrical ether
|
|
|
3 alcohol -> ether
|
H2SO4___ethanol
|
|
|
alkoxide -> ether
|
alkoxide + alkyl bromide = SN2
best w/ 1 alcohol, ok with 2, doesn't occur with 3 |
|
|
Alkene -> epoxide
|
1. Br2__H2O
2. NaH |
|
|
Nucleophilic ring opening of epoxides
|
nucleophiles: RO-, RS-, CN-, N3
|
|
|
Alkene -> epoxide
|
McPBA (butterfly mechanism)
|
|
|
Alkene -> glycol
|
OsO4___TMAO
TMAO = trimethyl amine oxide |
|
|
1 or 2 alcohol -> alkyl bromide
|
PBr3
good w/ acid sensitive reagents |
|
|
1 or 2 alcohol -> alkyl chloride
|
SOCl2
|
|
|
Alcohol -> alkyl halide
|
H-X (X= halide)
2 and 3 alcohol react by SN1 1 require heat (1 carbocation) |
|
|
Alkene -> alcohol
|
H2SO4
|
|
|
Alkene -> anti-markovnikov addition of Br
|
HBr, peroxides
|
|
|
Alkene -> Alkane
|
H2___Pd/C
|
|
|
Alkyne -> alkyl halide
|
HBr____CH2Cl2
=geminal bromide * good for grignard |
|
|
2 alcohol -> Ketone
|
Na2CrO4 + H3O+
(redox reaction) |
|
|
glycol -> ketone
|
pinacol rearrangement
H2SO4 |
