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Zn(Hg) - PowerPoint PPT Presentation
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Problem. Review from Monday. C. H. 3. C. H. C. H. 3. 3. C. H. C. l. C. H. 3. 3. A. l. C. l. 3. O. C. H. 3. Multiple Additions may be a problem You may get lots of ortho to throw away. C. l. A. l. C. l. 3. Problem. C. H. 3.
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Review from Monday
C
H
3
C
H
C
H
3
3
C
H
C
l
C
H
3
3
A
l
C
l
3
O
C
H
3
Multiple Additions
may be a problem
You may get lots of
ortho to throw
away
C
l
A
l
C
l
3
Problem
C
H
3
C
H
C
H
O
3
3
H
H
Zn(Hg)
+
H
H
Would it help
to change the
order?
HCl
O
O
O
O
C
H
C
H
C
l
3
C
l
3
+
A
l
C
l
3
A
l
C
l
3
C
H
3
Deactivating
group. No
Friedel Crafts
Z
n
(
H
g
)
H
C
l
C
H
C
l
3
A
l
C
l
3
O
Z
n
(
H
g
)
C
H
H
C
l
3
C
H
3
C
H
3
Electrophilic Aromatic Substitution Reactions
C
H
C
H
C
H
C
H
3
3
B
r
3
3
B
r
B
r
-
B
r
B
r
H
B
r
/
F
e
B
r
2
3
+
+
+
B
r
-
F
e
B
r
3
B
r
B
r
F
e
B
r
3
60% 39% <1%
C
H
C
H
C
H
3
3
3
B
r
B
r
B
r
H
H
H
C
H
C
H
C
H
C
H
3
3
3
3
B
r
B
r
/
F
e
B
r
Methyl does not help meta
2
3
+
+
Methyl
helps stabilize
ortho
H
B
r
C
H
2
B
r
B
r
H
(and para)
para
60% 39% <1%
Electrophilic Aromatic Substitution Reactions
B
r
B
r
B
r
-
B
r /
H
+
B
r
-
F
e
B
r
3
Two more
C
l
-
C
l
/
A
l
C
l
3
F
e
B
r
3
C
l
N
O
S
O
H
2
3
O
C
H
-
C
l
/
A
l
C
l
3
3
C
H
C
l
3
A
l
C
l
3
C
H
3
O
Friedel Crafts Alkylation
C
C
H
3
Friedel Crafts Acylation
O
N
O
O
/
H
S
O
H
N
O
H
N
O
2
4
3
no reaction
N
-
H
O
Electrophilic Aromatic Subsitution
How can you make HNO3 a stronger acid?
Add another acid.
O
H
N
O
O
O
O
O
O
N
H
H
N
S
H
S
O
O
O
O
O
O
O
O
O
N
i
t
r
o
n
i
u
m
i
o
n
H
H
O
S
O
H
3
O
Fuming
S
H
S
O
H
2
4
no reaction
O
S
O
O
Electrophilic Aromatic Subsitution
How can you make H2SO4 a stronger acid?
Add another acid.
O
O
O
+
-
H
O
+
H
S
O
+
H
S
S
H
S
3
4
O
O
O
O
O
O
O
H
O
H
Now that we have all our reactions, lets summarize
activation and deactivation
Electron Donating Groups activate the ring
Best
O
H
C
C
H
3
3
C
H
N
H
N
H
N
3
2
Which
one is
not
a
EDG?
A B C D
C
H
O
3
H
H
C
O
O
3
O
O
H
C
O
3
Direct
substitution
ortho/para
E F G H
Now that we have all our reactions, lets summarize
activation and deactivation
Electron Withdrawing Groups deactivate the ring
Best
H
N
O
O
O
O
N
H
N
H
3
2
C
S
O
H
N
3
+
H
anilinium
aniline
C
H
C
H
3
3
H
O
R
O
O
O
H
N
O
- EDG or
- EWG
?
Direct substitution meta
O
O
H
O
O
O
O
O
H
O
p
k
=
9
.
9
9
a
O
H
N
N
O
O
O
O
O
O
H
C
H
C
3
3
p
k
=
7
.
1
5
p
k
=
1
0
.
2
1
a
a
Predict pKa
N
O
O
A. less than 10 B. greater than 10
-H
-NO2
-OCH3
-CH3
-CN
-COCH3
-CF3
-F
-Cl
9.99
7.15
10.21
X
X
O
H
O
10.26
8.61
8.05
d-
8.68
inductive
effect
resonance
effect
9.89
9.41
l
What about a halide? Does a Cl
activate or deactivate the ring?
d-
C
l
C
l
C
l
C
l
d+
inductive
effect
resonance
effect
Cl poor at
p bonding
Deactivates,but directs ortho-para
