Br2
?
2 eq NaNH2
?
?
Pd/C
?
H2
H
?
?
?
?
?
1) (sia)2BH
2) H2O2
NaOH
H
HgCl2
H2SO4
H2O
?
Write out the mechanism
for each of these reactions
?
2 eq HBr
H
?
O
Pd(PPh3)
TEA
+
?
Br
2
2 eq Li˚
Br
O
?
?
?
MeMgBr
MeMgBr
O
O
Br
O
MeLi
O
?
CuI
HCN
KCN
2 eq MeLi
O
?
2 eq MeMgBr
MeLi
O
Ni
H2
NaNO2
?
HCl
O
PPh3
Br
O
?
OH
H
mechanism ?
+
OH
?
OMe
?
?
?
OMe
n-BuLi
?
TsOH
Benzene
reflux
Dean-Stark
?
?
?
O
1)
O
H-A
+
?
benzene
reflux
Dean-Stark
N
H
O
1) 1.1 eq LDA
2)
O
?
2) H3O
H3O+
?
Zn(Hg)
?
HCl
Pd/C
?
H2
?
1) 0.9 eq LDA
?
2) PhCH2Br
H
O
O
O
MeO
OMe
1) NaOH / H2O
?
H2CrO4
O
SOCl2
?
?
2) H3O+
3) ∆
NaOMe
Ph2CuLi
?
?
H
O
Cl
?
AlCl3
LiAlH4
O
3 eq Br2
4 eq NaOH
O
?
MeOH (XS)
?
TsOH
?
?
TsOH
MgBr
H
N
1) CO2
H3O+
O
?
2) H3O+
∆
?
SOCl2
?
Mechanism?
MeOH
1) 2 eq MeMgBr
?
2) H3O+
?
H
N
LiAlH4
?
O
O
2
NaOH
H
H2O
H3O+
O
2
H
O
?
Mechanism?
?
Mechanism?
NaOEt
OEt
?
EtOH
O
O
H3O+
?
+
Mechanism?
O
O
EtO
O
NaOEt
OEt
EtI
?
H2SO4
AlCl3
PhCH2Br
Cl
HNO3
Cl2
?
NaOEt
?
AlCl3
Acetyl Chloride
AlCl3
H3O+
?
∆
NBS
?
Peroxide
?
Zn(Hg)
HCl
?
?
?
NBS
?
Peroxide
C
NO2
NaN3
1) LiAlH4
N
Acetyl Chloride
AlCl3
?
Br2
?
AlCl3
?
2) H3O+
Acetyl Chloride
?
2) H3O+
1) LiAlH4
?
?
Zn(Hg)
HCl
1) LiAlH4
NaNO2
HCl ( 0˚C)
?
O
1) NaOH
NH
O
H Br
1) NaN3
2) LiAlH4
?
?
∆
MeI (XS)
CuCl, HCl
∆
O
H3O+
?
2) cyclohexyl
bromide
?
2) H3O+
?
1) AgO
H2O
?
2) ∆
H
H Br
H
Me2N (XS)
?
H2O2
?
∆
?
?