Exam III Flashcards
SN2
bimolecular
inversion of configuration (R -> S)
1 step done
aprotic solvent
SN1
unimolecular
step-wise
racemic
protic solvent
Alcohols & PCC
1 Aldehyde
2 Ketone
3 no rxn
weaker than Jones Reagent
E2
anti-periplanar
strong bases
one step
E1
presence of weak bases (CH3-OH, H2O)
two step
LG better on axial position (idc about antiperiplanar)
Strong Nucleophiles
Br-, I-, CH3S-, OH-,
RS-, OR-, R-C=_C-,
CN-, N3-
Good Nucleophiles
Cl-, F-, CH3-C(=O)-O-, R-C(=O)-O-
CH3SH, RSH, R2S,
NH3
Bad nucleophiles
H20, ROH, R-C(=O)-OH
Alcohol Reduction
oxygen loss
hydrogen gain
Alcohol Oxidation
oxygen gain
hydrogen loss
Alcohol Substitution
make good leaving group (sn2)
Alcohols & Jones Reagent
1 RCOOH
2 Ketone
3 NR
How to make ethers
Alkane Oxymercuration
Williamson Ether Synthesis (Na-NH3)
H2SO4
How to make epoxides
McPBA
X2, base
How to open epoxides
Basic (less substituted)
Acidic Conditions (more substituted)
LiAlH4
Alkane oxymercuration
Mark, Syn
Used to make ethers
Williamson Ether synthesis
SN2, NaR, Na0, NaH
Ether Cleavage
SN2 - HI
SN1 - HBr
KOH
E2 on alkyl halides
H2SO4
E1 on alcohols
Hoffman major
no hydrogen on anti to leaving group on cyclohexane
aprotic solvent
SN2, cannot hydrogen bond
DMSO, DMF, acetone, ACN, CH2Cl2, DCM, THF
protic solvent
SN1, can hydrogen bond
H2O, HCOOH, CH3OOH, EtOH, CH3COOH
Alcohol (mechanism)
H2O (know mechanism)
SN2 LG ranking
primary is better
SN1 LG ranking
tertiary is better
hydroboration
anti-mark, synaddition
oxymercuration
anti-mark, anti addition
