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Practice
Problems
Provide
mechanisms,
and
where
appropriate
products,
for
the
following
reactions:
1)
O
Cl3C Cl
O
N N
H H CCl3
2)
Br
O N O Br
N N
iPr3Si iPr3Si
3)
O O HCl, heat O
NH2
+
N
Me
N
Me
4)
H O
OH NaOH, CHCl OH
3
5)
CH3CH2CH2Cl, AlCl3
6)
O
O O
Et2NH heat
Br
O
O
1
Aromatic
and
Heterocyclic
Chemistry
Jonathan
W.
Burton
7)
Me N Me
Br
Mg, then Ph C18H17N
F
8)
i) Na H O
ii) Cl S Cl
Me
HO OH O
a polymer
Me
9)
CO2Et
O O O
+
CO2Et
OEt EtO2C N
NH2 H
10)
O
SiMe3 KF
Ph
O O
OSO2CF3
Ph Ph
O Ph
11)
Cl3CCO2Na
diglyme, ∆
Cl
12)
O2N
Me Me
i) F NO2
2
Aromatic
and
Heterocyclic
Chemistry
Jonathan
W.
Burton
14)
CO2Et
HC CCO2Et
OH Et3N, ∆ N
N
CO2Bn CO2Bn
15)
O
Cl NH2
H
NHNH2 EtOH, ∆ N
H
16)
i) Na, NH3(I), EtOH (1 equiv),
then NH4Cl, then H3O+
N ii) NaOH O
17)
EtO2C
∆
+
CO2Et
18)
Cl
Cl
O
C10H14
AlCl3 AlCl3
19)
NO2 HCl, NaNO2, 0 °C H2N
P(OMe)3
C12H9N
heat then heat N
H
20)
MeO i) Na, NH3 / EtOH O
ii) H3O+
MeO COOH COOH
MeO O
3
Aromatic
and
Heterocyclic
Chemistry
Jonathan
W.
Burton
21)
O•
2 equiv.
N
KO3S SO3K
OH O O
22)
H OH Me
N
NMe MsCl, Et3N
CO2tBu CO2tBu
N N
H H
single enantiomer racemate
23)
NH O
NO2 N
i) H2N NH2 N
160 °C 80 °C
25)
O O EtONa, EtO2C S CO2H
+ EtOH
EtO2C S CO2Et
Ph Ph
Ph Ph
25)
For
the
following
compounds,
suggest
a
synthesis
from
the
unsubstituted
aromatic
parent
stated
in
parentheses;
more
than
one
step
may
be
required
in
each
case.
CN
F Br
Ph CHO
O
N
H
(benzene) (benzene) (indole) (furan)
26)
Suggest
syntheses
of
the
following
from
either
benzene
or
toluene.
I
Me F
Br F
Br Me
4