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NaOH
XR

LDA, THF

NaOEt, EtOH

SOCl2

PBr3

TSCl, Pyridine

HX

NaSR

NaOR

NaSH

NaOH

NaH

RX

NaOH
RX

NaOH/NaH
R’-X, DMF

(2) NaOH/NaH
(2) RX

H2SO4 heat

Excess HX heat

PBr3
H20

TMS-Cl, NEt3

TBAF

KOH, RCH2X
H3O+ OR H2N-NH2

NaN3, DMF
LiAlH4
H20

PCC, CH2Cl2

Na2Cr2O7, H2SO4(aq)

Na2Cr2O7, H2SO4(aq)

Na2Cr2O7, H2SO4(aq) OR PCC, CH2Cl2

LiAlH4
H3O+
OR
NaBH4, CH3OH

NaCN, DMF

Excess LiAlH4
H2O

Excess LiAlH4
H2O

NaNH2
XCH2R

H2(g) pd/c

Na(s), NH3(l)

H2(g), Lindlar’s cat.

NaOH(aq), Br2

Zn/HCl

NaIO4

H2O2

2H2O2

HSCH2CH2SH [H+]
Raney Ni H2(g)

Amine, NaBH3CN, pH=4-6

NH2R, NaBH3CN, pH=4-6

NH2NH2
KOH, heat

R–=PPh3

Ester stabilized ylide

H2O, H3O+

Hg(OAc)2, H2O
NaBH4

BH3, THF
H2O2, NaOH

Br2

H2(g), pd/c

Br2, H2O
NaOH

mCPBA

H3O+

OsO4
NMO

O3
SMe2

O3
H2O2

O3
H2O

O3
H2O

Nu-
H3O+

LiAlH4/DIBAH
H2O+

H2SO4, EtOH

NaOEt
epoxide
H+

Excess NaNH2, NH3(l)
H2O

HCl

HX

2 eq. Br2

H2SO4, H3O+

R2BH, THF
NaOH, H2O2

[H+] cat.

HX

eq HX