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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