C, H, O, N, S, F, Cl,

Br, I P
C C
(open chain)
(linear chain) (branched chain)
(cyclic or closed chain)

 ( )

(Hydrocarbon fuels)

 (bond)

8 A (octet rule )
-
-
-

 2
1.


2.



1. ()
2.

 3
1. (Metallic bond)
2. (Ionic bond)
3. (Covalent bond)

(electron sea
model)

(ionic bond) ion+ ionion+ ( En )

ion-
11 Na (2, 8,1)
17 Cl (2, 8,7)

.. + .. Cl ..
Na
..

Na +(2, 8 )
-

Cl (2, 8, 8)
NaCl




( EN )

8 ------>

 1A 1 +1
2 2 +2

7A
1 -1 5
-3 3

II

III

IV

VI

VII

+1

+2

+3

-4

-3

-2

-1

 EN

EN

F O
N Cl Br
4.0 3.5 3.0 3.2 2.8

I
2.5

S
2.5

C
2.5

H
2.1

EN Cl > N Cl > N
EN N > Cl

P
2.1

polar covalent bond

2.
- ( )
- ( )
EN (EN)
2.1
EN

H H

2.1 2.1
EN = 0

2.2
H Cl
EN

2.1 3.2

EN = 1.1
2.3

1- 2+ 1O C O
EN

3.5 2.5 3.5

Cl

H
H

C
C

Cl
EN 2.1 2.5 3.2

H
H
EN 2.1 3.5 2.1

polar covalent bond

Electronegavity (EN)
H

Br

Cl

(dipole moment)

H
H

polar and non-polar molecules

Cl

Cl
Cl

Cl
Cl

H
H

polar
= 1.87

non-polar
=0
403221-introduction

16


1. (single bond)

2. (double bond)
3. (Triple bond)

1. (Single bond)
1

H2

F2

2. (Double bond)
2
CO2

3. (Triple bond)
3



e- e-

(atomic orbital AO)

(molecular orbital MO) 2

1. (bonding molecular orbital

BMO) e-

2. (antibonding molecular orbital

AMO) e-

* s

.A
+

.B
+

.A .B
+

. .
BMO s

.A
+

.
+

.A .
+

AMO s

 * * p

.
.
(1)

.
.

. .

. .
p

..

p
(2)

p
p

 e-
1. BMO AMO
*
2.
3. e- e- 2 e4. e-
5. e-
6. e-

 (bond order bond number)

= e - BMO - -e AMO
2

 H2 N2

2p

Increasing energy

2p x 2p y 2p z

2p
2p

2p
z
2p 2p
x

2s

1s

2s

2s

1s

1s

A2

2p x 2p y 2p z

2s

1s

 O2 Ne2

2p

Increasing energy

2p x 2p y 2p z

2p

2p

2p

2p

2p
2s

1s

2s

2p x 2p y 2p z

2s

1s

1s

B2

2s

1s

 e- (1) N2 (2) O2

2p

2p

Increasing energy

2p x 2p y 2p z

2s

1s

2p 2p

2p
2p 2p
2s
2s

1s

1s

N2
(1)

2p x 2p y 2p z

2p x 2p y 2p z

2p 2p

2p

2p

2p x 2p y 2p z

2p
2s

2s

1s

1s

2s

2s

1s

1s

O2
(2)

2s

1s

N2 e-

(1s)2(*1s)2(2s)2 (*2s)2(2p)2 (2p)2 (2p)2

10 - 4
N2 =
=3
2
N 2 1 2

O2 e (1s)2 (*1s)2(2s)2 (*2s)2(2p)2 (2p)2(2p)2 (*2p)1 (*2p)1

8
4
O2 =
2

=2

O2 1 1


C
4
(covalent bonds) 4 (single bond)
(double bond) (triple bond)

(single bond)
(double bond)
(triple bond)
()

Atomic Orbitals

403221-introduction

31



n=1
2 2,3,4 8,18
32 4
32


(Orbital)
4 s,p,d f

1
2
3
4
5

s
sp
spd
spdf
spdf

-
2 s
-IIIA - VIIIA p
d - f


n n
l n=3
3s < 3p < 3d p 3 px, py pz
d 5 dx2 - dy2, dz2, dxy, dyz,
dxz
degeneracy

Atomic Orbitals

2s

2px 2py 2pz

403221-introduction

37

Atomic Orbitals

1.
2 ( )
o

(spin up)

o (spin down )

2. (
)


(Hunds rule)





(
)

 (Complete subshell)

(Incomplete subshell)

(Half-filled subshell)

 e (degeneracy)
e-
e-

2p6 2p3
2p3 2p4
3d10 3d9


#eH

He

Li

Ne

10

Na

11

1s

2s

2px

2py

2pz

3s

1s1

1s2
1s2 2s1

1s2 2s2 2p2

1s2 2s2 2p4
1s2 2s2 2p6
1s2 2s2 2p6 3s1
[Ne] 3s1


(Atomic number) 6 6
(Electronic configuration)
6 (Orbital)

C6 =

1s 2 ,2s 2 ,2 p1x ,2 p1y ,2 pz0


(Hybridization)
2

s p
sp3
sp2
sp

(single bond)
(double bond)
(Triple bond)

 (sigma, -bond)
head on overlap

s-s orbital

p-p orbital

403221-introduction

48

 (pi, -bond)
side by side overlap p

-electron

403221-introduction

49

 (Hybridization of carbon)
C 4
s = 1 ( )
p = 3 ( )

 (hybridization)
1. sp3 s 1 p 3
CH 4

H
C
H H H

1H
6C

=
=

1s 1
1
1s2 2s 2 2p x

2p y

2p z

Energy

sp 3

2p x 2p y 2p z

2p x 2p y 2p z

hybridization

promotion

2s

sp3

sp 3

sp3

sp 3

2s

1s

1s

1s
C

sp3-hybridization

403221-introduction

52

403221-introduction

54

 methane, ethane

403221-introduction

55

sp3-hybridization
Nitrogen

Oxygen

2p

sp3
4 orbitals

2s

1s

403221-introduction

56

 methanol (CH3OH)
2
2
2
1
1
1
s
,
2
s
,
2
p
,
2
p
,
2
p
O8 =
x
y
z

Oxygen
sp3
4 orbitals
H
..
H C
O:
H
H
403221-introduction

57

2. sp2 s 1 p 2
3

(1)

Energy

sp2 hybridization 1 (1 1 )
C sp2 2

2s

2s

1s

1s

sp

sp 2

sp 2 sp

sp 2

C=C

pz
sp

H
sp

sp 2
1s

pz

H2

2p z

hybridization

promotion

pz

(2)

2p x 2p y 2p z

2p x 2p y 2p z

sp2
sp2

sp2-hybridization
Carbon

2p
sp2
3 orbitals

2p
2s

1s

403221-introduction

59

sp2-hybridization

403221-introduction

60

 ethene (C2H4)

403221-introduction

62

sp2-hybridization
Nitrogen
2p

Oxygen

2p
sp2
3 orbitals

2s

1s

403221-introduction

63

 formaldehyde acetaldehyde
formaldehyde
CH2O

acetaldehyde
CH3CHO

403221-introduction

64

3. sp s 1 p 1
2

(1)

Energy

sp hybridization (triple bond) 1 (1

2 ) C sp 1
ethyne
hybridization

promotion

2s

2s

1s

1s
py

(2)

sp

sp sp

sp
1s

py

pz

2p y 2p z

2p x 2p y 2p z

2p x 2p y 2p z

pz

sp

H-C

2
C-H

sp-hybridization
Carbon

2p
sp
2 orbitals

2p
2s

1s

403221-introduction

66

sp-hybridization

403221-introduction

67

 ethyne (C2H2)

403221-introduction

69

sp-hybridization
Nitrogen

Oxygen

2p
2s

No sigma bond

2p
sp
2 orbitals

1s

403221-introduction

70

 CH3CN allene
CH3CN

Allene CH2=C=CH2
H

H
C
H

C
H
403221-introduction

71

 ethyne ethene ethane

ethyne

ethene
403221-introduction

ethane
72

1
4
1.
2.
3.
4.


Lewis Structure
H

H C C C C H

H C C N

H H H H

C
H
H
C
H C
H C
C
C
H
HO
H H

H
H
H

C
C

C
N

C
C

Condensed Structure
CH3CH CH CH3
CH3CH2CH2CH2CH2CH3
CH3(CH2) 4CH3

H2C

CH3C N
CH3CN

CH2

CH
CH

HC
HO CH2

HC
HC

CH
N

CH
CH

Line-angle Structure
N

HO

403221-introduction

74

H
H

2.1 (Extended structural formula)

( )
C 4
N 3
O 2
H, F, I, Cl, Br 1
1 1 (2 )

 (Bond line convention structure)

C H C

()
C H

2.3 (Partially extended structrural

formula)
( -OH,
-COOH, -NH2, -CHO, -CONH2)

 (Condensed structural formula)


1 ion-
ion +
(1x2) + 6 = 8
4 + (6x2) = 16
5 +(1x4) - 1 = 8
5 + (6x3) +1= 24
NH 4+

H 2O

NO 3-

CO 2

2 e-

H2O

CO2

HCN

NO3-

 3 e- 1

.. ..H

H O

..C ..O

O
..
O..N ..O

4 e- H = 2

..
..

..

..
..

..

..
..

..O
..
..
..
..
..
O..N....
O
H..O ..H .. O ..C ....
O.. ..
..
5 e-
..O
..
..
..
..
..
..
O..N....
O
H....
O ..H .. O ..C ....
O.. ..
..

 6 e- e Be = 4 B = 6 ion [ ]

..

..

..
..

..O
..
..
..
..
..
..
..
..
..
..
O
N
O
H....
O ..H
O C....
O
..
..
..

1 e- 1

H : C ::: N
O :: C :: O

= HCN
= O=C=O

4, 5, 6, 7 e- 8 PBr5 SI6