Chemistry 108B Exam 2 Cheat Sheet--Woo Hoo!!!! Synthesis of ALKANES R2 R1 H2, cat. EtOH Synthesis of HALIDES R2 R1 X
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Chemistry 108B Exam 2 Cheat Sheet--Woo Hoo!!!! Synthesis of ALKANES R2 R1
H2, cat. EtOH
Synthesis of HALIDES R2
R1
X2 R2 hν X = Cl, Br, I
R1
cat. = Pd/C or Pt/C
R1
R1 C C
RCH2
2 H2, cat.
R1
EtOH H2O
MgBr
R
R2
O
RCH3
O H2, cat.
R
O
OH SOCl2
R R
O
R
1) Hg(OAc)2 (aq) 2) NaBH4
R
1) BH3, THF 2) NaOH/H2O2
R
HX R
R2
R
X
HX R2
Synthesis of ALCOHOLS X
N
O
X
R
R
R
N
R1
Br
R
R
Lv = Cl, Br, I, OTos
NBS R
OH conc. H(+)
R
R
R
N
R3
Ph3P C
R1
R2
H
H
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
O
Cl
R
HNO3/H2SO4
R1 C
-78 °C
Br
R
O AlCl3 R
R2
Synthesis of ALKYNES R2
X
C
NO2
S o
m
m
Synthesis of EPOXIDES O R
R1
O O
R
R1
O
R2 O
OH
R2 HO R
R2
R1
R1
O
R
R1
R2
+
R2
R1
OH
O PCC or Jones or R1 R2 R2 NaOCl
Lv R1
RNH2
R C C
R2
O
OR2
R3
R2
R2
Cl
R4
R1
R
HgSO4, H3O(+) or R 1) R2BH 2) H2O2, NaOH
O3 or KMnO4/H(+)
O
NR R1
R
O
AlCl3
For R C C H : HgSO4 = R1
R1
H(+)
O
+
Synthesis of IMINES
O
OH(-) X
OH
OsO4 or KMnO4/OH(-)
Synthesis of ALDEHYDES/KETONES O PCC R OH or R H Dess-Martin
R
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
o
R2
OH
SO3/H2SO4
R2
OH
R1
O
E. A.S. Reactions X2, FeX3
R1 OH
R1
Li, NH3
OH
R2MgBr
O
X
R
LiAlH4
R1
R
R
R2
BH3 or LiAlH4
OR2 O
X
X2
R2 R3
OH
R1
X
FeX3
R3
R1
R2
O
R X2
, 0 °C O
Br
NBS
R2 OH
R3MgBr
R
Br
R
POCl3
OH
R1
O
R
OH
H
R1
For 3° ROH's: conc. HX, 25 °C
R2
R2MgBr
O
R
R
R1
R2
R1
Synthesis of ALKENES NaOH
OH
R
NaBH4
O OH PBr3
OH
R
OH
O Cl
R
H
R R
Lv
NaBH4
OH
R
O R
CH3
R2BH =
R3
+
O R1
O
R
O R1
R22CuLi Cl
O
R2
H
O R2
R4