3. Substitution, addition, and elimination reactions
1. Discuss the directing effects on the course of the substitution reactions in the aromatic compounds of the following
substitiuents: a) cyano, b) phenyl, c) N-ethylamino, d) methoxy, e) carbamoyl, f) triphenylmethyl, g) acetyl
2. Draw the structures for the products of the following ractions:
O
F
+
CH3
N
-
Li / NH3
a)
O
f)
Br2,
NBS / CCl4, (BzO)2 CH3I
FeBr3
b)
NO2+
d)
e)
g)
KMnO4/H2O OH-
+
N
-
c)
O O
O
Ph
H3C
CH3 -
Ph
t-Bu O +
1. O3
P
Ph
t-Bu OH
2
- , THF
NBS, h½, CCl4 2. Zn, H+
h)
CH
j)
Cl i)
k)
O
Mg, Et2O 1. ethanal
POCl3, 1.
SOCl2,
2. H3O+
Mg, Et2O
HBr 2. H3O+
pyridine
l) m)
n) o) pyridine
p)
r)
s)
Br
H
H3C
H CH3
OH
POCl3,
Br2 H3C H t-Bu O- 1. RCOOOH
pyridine
t)
u)
CH3 2. H3O+
H
v)
w)
t-Bu OH
SOCl2/pyridine
Ts-Cl,
pyridine
z)
O
Cl-
x)
y)
a)
CH3
3. Find a method of the synthesis (write reactions):
H3C
CH3
O
b)
H2C
i)
OH
O
HO
c)
e)
OH
OH
OH
d) CH3
O g)
O
Cl
h)
O f)
CH3
H3C
Cl
Br
HO
CH3
CH3
CH3
4. Find a mechanism and explain reaction course.
HBr
Br
+
5. Suggest a synthesis of: a) n-propylbenzene from benzene, b) m-chloroethylbenzene from benzene,
c) 2-methyl-1-butanol from butanone, d) benzyl alcohol from benzene e) ethylidenecyclohexane from
methylenecyclohexane, f) acetone from acetylene, g) o-crezole from benzene, h) 1-methylcyclohexene from
cyclohexanone