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Synthesis of ALKANES
R2
R1
H2, cat.
EtOH
Synthesis of HALIDES
R2
R1
X2
R2
h
X = Cl, Br, I
R1
R1
R1 C C
RCH2
2 H2, cat.
R1
EtOH
H2O
MgBr
R2
RCH3
O
H2, cat.
OH SOCl2
R
R
1) Hg(OAc)2 (aq)
2) NaBH4
1) BH3, THF
2) NaOH/H2O2
HX
R
R2
HX
R2
Synthesis of ALCOHOLS
X
R1
Br
NBS
R
OH conc. H(+)
R3
Ph3P C
R1
R2
R1
-78 C
R1 C C
R1 C C
Br
X = Cl, Br, I
H2
R2
Lindar's cat. R1
RX, AlX3
R2
R1
Li, NH3
R2
-78 C
R1
2 NaNH2, NH3
Cl
HNO3/H2SO4
R1 C
-78 C
Br
O AlCl3
R
R2
Synthesis of ALKYNES
R2
NO2
S
o
Synthesis of EPOXIDES
O
R
R1
O
O
R1
R2
O
OH
R2
HO
R
R2
R1
R1
R1
R2
R2
R1
OH
O
PCC or Jones
or
R1
R2
R2
NaOCl
Lv
R1
RNH2
R
C C
R2
OR2
R3
R2
R2
Cl
R4
R1
HgSO4, H3O(+)
or
R
1) R2BH
2) H2O2, NaOH
O3
or
KMnO4/H(+)
NR
R1
AlCl3
For R C C H : HgSO4 =
R1
R1
H(+)
Synthesis of IMINES
OH(-)
X
OH
OsO4
or
KMnO4/OH(-)
Synthesis of ALDEHYDES/KETONES
O
PCC
R
OH
or
R
H
Dess-Martin
R2CH2
OH
R1
R1
S = substituent
o = ortho
m = meta
p = para
1) Hg(OR2)2, R2OH
2) NaBH4
R2
R1
X2/H2O
R
R1
R1 O(-)
OH
H3O(+)
Synthesis of ETHERS
O
OH
OH
R1
SO3H
p
R2
OH
OH(-)
R1
R2
OH
SO3/H2SO4
R2
OH
R1
E. A.S. Reactions
X2, FeX3
R1
OH
R1
Li, NH3
OH
R2MgBr
LiAlH4
R1
R2
BH3
or
LiAlH4
OR2
O
X2
R2
R3
OH
R1
FeX3
R3
R1
R2
R
X2
, 0 C
O
Br
NBS
R2
OH
R3MgBr
Br
POCl3
OH
R1
OH
R1
R2
R2MgBr
R1
R2
R1
Synthesis of ALKENES
NaOH
OH
NaBH4
O
OH PBr3
OH
OH
O
Cl
R
R
Lv
NaBH4
OH
O
R
CH3
R2BH =
R3
O
R1
O
R1
R22CuLi
Cl
R2
O
R2
R4