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NABH4
weak reducing agent
LAH
strong reducing agent
LAH and NABH4 are associated with
reduction runs
X=
-Cl, -OH, -OR
LAH
If -X = -OH, the second product is
H2O
If -X = -OR, the second product is
ROH
To add an R group, react with
R-Li or R-MgCl
X=
-Cl or -OR
H2SO4, E1
HBr, SN1
HI, SN2
no rxn
oxidation rxn
oxidation
oxidation
weak oxidation rxn reagents
PCC, swern, DMP
strong oxidation reagents
CrO3, H2SO4, K2Cr2O7, NaOCl
TsCl
Lucas Reagant
ZnCl2/HCl
Rate of rxns
3rd degree > 2nd » 1st
no rxn
PX3 where X = Cl, Br, I [SN2]
SOCl2
ester formation
h+
ester formation mech
protecting groups
R-OH
TBAF provides the
F: -
F: - provided by
TBAF
R-OH
R-OTMS
TMSCl
F: -
TMSF
R-O: -
W.V.
R-OH