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. :
4 x 15 ( )
3 x 10 ( )
o : 3-5
: 25
(I ): 15 - 30
(): 40
O :
Mmmmmmmmhhhh!!!!
(1879): 300
O
NH
SO2
Bulletproof!
CO2H
O
CH3
H
N
C6H5CH2
O
O
N
H
OH
O
OH
CH3
CO2H
CH3
HO
O OO
O
1. :
() ;
o je ( )
()
Whler (1828):
je
NH4 OCN
CH4N2O
NH2CONH2
-
2. : ()
-
()
()
e :
e- s- i p-
e- iz d- orbitala (M-; II III )
e- d- i f- o (
)
()?
A 1 + A 2
A:A A-A
(E)
2
1.
(Coulomb-o ).
2.E ( ).
3. E
Jo o e je
,
e-
a 1
Na
2,8,1
e- +
a 2
+
Cl
2,8,7
e+
e
- a
[Na
2,8]+
[Cl
2,8,8]-
Ko
+
e-
A 1
e-
A 2
H H
Cl
Cl
Cl Cl
Cl
H Cl
e-
e-
Ko
()
e
H
H
C H
H
Koo- : e
e
A B
Koo
H
H N
H
R3N
F
+
B F
F
+ O
H
H N
H
F
B F
F
R3N O
T-o
jo,
E
0.3
<
0.3 2.0
<
2.0
j
O - ()
( )
M
:
:
H : H Li : H : F: F:
:
:
: F: Be
:
ne
: F: Be : F:
180
H O
T :
:
:
: Cl : B
Cl
Cl
:
N
H
H
H
H
C
H
H
H
H
H
Ko -
1897.- e- ( )
? ( )
K ?
( )
?
( )
1923. DeBroglie
h
mv
1926. Schrodinger e-
e-
e-
Ko-o ,o
, o o
90-95%
4 :
n e
n = 1-7
l ,
l= 0, 1,2...(n-1)
M . m
m = 0, +1, -1, +2, -2, ..+l, -l
s-
s= -1/2 +1/2
K ?
?
s-
p-
2s
1s
px
py
pz
1 s-
2s-
s-Orbital
2p
p-Orbital
: ?
2s
1s
px
py
pz
es (He)
1.
2. Pauli: : 2e- .
3. Hunds- : o je
(px,y,z) 1 esvaka
+/- =
(Linus Pauling)
( )
+
0
+ +
++
0
-
1s1
H
1s1
+
H2
+ +
+
-
+
-
+
-
( )
( )
He ?
E (MO)
A (MO)
E H
H2
+E
-E
He
-E
He
MO
2 e-
2 e-
+E
MO
He2
e
4 e-
MO
( )
1. A
(1s 1s 1s 3s)
2.
A
() (
) .
BeH2 ,
-
Be 1s2 2s2
o
sp
a , ,
sp-
hibridizovane sp orbitale koje su linearne strukture
2s + 2p = 2 sp
s-veza
- sp o : 50% 50% p
- : 180
2 p o
sp2
BH3 ()
2s 2 p o 3
sp2 o (
120) s + 2p = 3 sp2
s-veza
p-
sp3 hibridizacija
CH4
1s i 3 p o 4 sp3
o ( 109,5)
s + 3p = 4 sp3
s-veza
s- 2 sp3
s-veza
Ethane
s- ,
p-o
p- p-o
a) ( )
b)
.
: d+ i d( ).
d+
d-
Pauling-
0.3
<
0.3 2.0
<
2.0
d+
d-
d+
C-Y
d+
a)
CH3
d-
Cl
d+
O Cl
CH
CH3 Cl
d-
d+
d-
d3
Cl
d+
Cl
K
N
d-
R2
H
C N
C N
H
R2
H
H
R
) C-N
e e (+)
ja s-
d-
H
R1
d+
-H
C O
H
C O
H
) -
C-O-
(m) je
m=q d
(10-8 cm = 1 A)
Je m je Debye [D]
d+
d-
m=5D
m = 1.2 D
) C-H
H
R1
m ~ 0.3 D
<
C C
H
H <
C C
H-
) Mo
C C
C
Cl
Cl
Cl
Cl
Cl
Cl
m=0
trans- 1.2-
H
C C
cis- 1.2-
Cl
N
H
H
m = 1.47 D
N
F
m = 1.85 D
Cl
m = 0.23 D
( s )
s
d+
C3
dd+
C2
ddd+
C1
d-
Cl
H
dd +
H
d+
d-
Y
e
H
-I e
Z
s
Z
H
+I e
(-I)
R3C
R3C
N
O
I e
I e
>
C6H5
Cl
>
>
Br
>
>
CH CH2
COOH >
I
>
>
OH
C O>
R
>
CH CH
OR
>
CH3
< CH3<
CH2 CH3< CH
CH3
CH3< C
CH3<
CH3
e
( +I e)
C O
O
Lewis-
1:
CO2
OCO
H
HC H
H
CH4
2:
:Br .
H.
.
. C. .
..
.O :
.
3: ()
(e H)
:
:
: F: F:
:
:
H: H
4:
. O
.
e : 2
, 1; a 2
+
H O H
H
+
H3O
?
6 e ()
-5e
+1
:N:::O:
H
H C
H
H
H C
H
:C:::O:
H
H C
H
CO2
O C O
1. :
2. O 6e, C 4e, 6
16e
3.
1. 2e 1 .
2.
.
..
:O..
..
O:
..
..
O
..
..
O
..
a)
: II Be, B
Cl Be Cl
-
H B H
H
b) e- - -
7 e
H C H
H
Mo ( e- od 8)
)
H B
H
H
B H
C
H
H H
H
+
C H
H
C H
H H
d) E P, S 8
10 e-
12 e-
()
:
Mo
, a
oA
A
B
Ka a CO32-
O
3
je (e)
e ,
-
3
2/3-
2/3-
2/3-
= e
=
1. (
p - )
CH3C
O
O
CH3C
O
O
p-
CH2 CH CH CH2
CH2 CH Cl
Cl
Cl C Cl
H
CH2 CH2
a s-
o ( )
2. ;
-
N N O
N N O
m= 0
1/2
1/2
N N O
3. e
O
C
O
O
C
O
C
O
4. (
(
)
Mo (ee)
o
1.
:N
O:
:N
..
O:
H
C
2.
C
-:
:O
..
C
H
H
C
:O:
(
)
I
() o II
()
II s
( )
E
Energija oblika II
Energija oblika I
( )
:
a)
)
) (-) (+)
2 ...
(R)
(p-)
A. () e
(+R) e;
H2C
CH
..
OCH
3
..
_
H2C
CH
+
OCH
3
..
()
p-e (-R)
O
H2C CH C
H
O
H2C CH C
H
H2C CH C N
H2C CH C N
a
. sa
+R
+ R efektom
gr.
(i( --I-efektom)
I )
. gr.
R sa
-R efektom
(i -I -efektom)
( I )
NR2
NO2
C N
OR
C O
R
C O
OH
OH
X (F, Br; I)
C O
OR
C O
Z
( )
je
a RH
nema
CH3CH2CH3
-X
CH CH CH Br
RX
a 3 2 2
a
-OH a CH3CHCH3
OH
2-
-SH CH3CH2SH
e
o
(a)
a
(a)
CH3 CH CH2
CH3 C CH
ArOH
ARH(R)
OH
R(H)
2-
K -C=O
a
ketoni
H C
CH3
CH3
CH3
H
O
CH3
O
OH
O
OCH3
a
CONH-
CH3
CH3
-COCl
CH3
CH3
C
C
O
O
CH3
e
CH3
NH2
C
Cl
O
NH