www.wunan.com.

tw
(02)2705-5066

 www.wunan.com.tw
(02)2705-5066

www.wunan.com.tw
(02)2705-5066

 www.wunan.com.tw
(02)2705-5066

email

www.wunan.com.tw
(02)2705-5066

 www.wunan.com.tw
(02)2705-5066

LewisLewis Structures

1.1

1.2

Molecules with Functional Groups

1.3

Unsaturated Molecules

1.4

Exceptions to the Octet Rule 22

1.5

25

1.6

Formal charges

33

1.7

Ions

38

1.8

Free Radicals

48

Resonance Structures

2.1

2.2

(I)

15

53
53
103

119

3.1

119

3.2

Sigma Bond Breaking

119

3.3

Sigma Bond Making

127

www.wunan.com.tw
(02)2705-5066

3.4

Simultaneous Bond Making and Breaking

133

3.5

Rearrangements

152

3.6

Ring closures

171

4.1
4.2

(II)

181

Bond Making and Bond Breaking

181

Bond Making and Bond Breaking

191

(III)

207

5.1

207

5.2

Complex Mechanisms

212

www.wunan.com.tw
(02)2705-5066

Lewis
Lewis Structures
1.1
G. N. Lewis

Berkeley
LewisLewis
StructureLewisStructure

point
HHOHHHOH

Lewis
Lewis

Lewis

www.wunan.com.tw
(02)2705-5066

1.2
Molecules with Functional Groups

1-1Methane

H
H C

H
HHCHH
1-Formicacid

O
C O H

HCOOH
covalentbond

.%
ionic bond

www.wunan.com.tw
(02)2705-5066

CH1  Lewis

STRUCTURE


electricpair
 nonpolar bondpolar
bond

Cl

Cl H

counttheavailablevalenceelectrons

Cl

Br

Mg

H
1-chloromethaneCHClH

Cl

www.wunan.com.tw
(02)2705-5066

H1ee
1C1ee
1Cl1ee
1e

H
1-methanol H C O H
H

H1ee
1C1ee
1O1ee
1e

H

 
octetrule


 H

www.wunan.com.tw
(02)2705-5066

CH1  Lewis

STRUCTURE

1.
1-chloromethaneCHCl

H
H

Cl

H
H

Cl

He
Cee
Cle1e
Cl


H
H

Cl

H
www.wunan.com.tw
(02)2705-5066

u n s h a r e d
electronsCl
1-methanolCHOH

H
H

H
H

C
H

H
H

H
 L e w i s

Lewis
1- 1-chloromethaneLewis

www.wunan.com.tw
(02)2705-5066

CH1  Lewis

STRUCTURE

H
H

Cl

C
H

ee
e
1e
CH  Cl1e
1-

1eLewis

1-1-chloromethaneLewis

H
H

e10e
e
1e

www.wunan.com.tw
(02)2705-5066

CHOH1e
1-

1eLewis

Lewis
1-9
DimethyletherCHO
Dimethylether

H
H

C
O
H

dimethyletherLewis

www.wunan.com.tw
(02)2705-5066

CH1  Lewis

STRUCTURE

H
H

Lewis



Lewis

H
H

C
H

H 1ee
C ee
O 1ee
0e

www.wunan.com.tw
(02)2705-5066

10

C
H

e1e

 ee
0e
Lewis

H
1-10
MethylamineCHNH
Methylamine

H
H

C
H

N
H

www.wunan.com.tw
(02)2705-5066

CH1  Lewis

STRUCTURE

11

C
N
H

methylamineLewis

H
H

Lewis



Lewis

H
H

C
H

H
N
H

www.wunan.com.tw
(02)2705-5066

12

H 1ee
C 1ee
N 1ee
1e

H
H

H
N
H

e1e

 1ee
1e
Lewis

H
H

C
H

H
N
H

www.wunan.com.tw
(02)2705-5066

CH1  Lewis

STRUCTURE

13

1-11
MethanethiolCHS
Methylamine

H
H

C
S

H

methylamineLewis

H
H

H
Lewis



Lewis

www.wunan.com.tw
(02)2705-5066

14

H
H

H 1ee
C 1ee
S 1ee
1e
methylamineLewis

H
H

H
Lewis
e10e

 ee
1e
Lewis

H
H

C
H

www.wunan.com.tw
(02)2705-5066

CH1  Lewis

STRUCTURE

15

1.3 Unsaturated Molecules

multiple bond

 Lewis

Lewis

1-1EthyleneCH
Ethylene

H
C

H1ee
1Cee
1e
EthyleneLewis

H
C
H

C
H

www.wunan.com.tw
(02)2705-5066

16

 H

H
C

Lewis


e10e

ee

1e
1e1e
Lewis
C

H
C
H

C
H

H
Lewis

 1e

1

www.wunan.com.tw
(02)2705-5066

CH1  Lewis

STRUCTURE

17

1e
LewisEthylene

1-1FormaldehydeCHO
Formaldehyde

H
C

H1ee
1C1ee
1O1ee
1e
 FormaldehydeLewis

H
C

H
Lewis
ee
ee
1e

www.wunan.com.tw
(02)2705-5066

18

1e1e
Lewis


H
C

H
H
Lewis

ee

1
ee
1e
1e
LewisFormaldehyde

1-1AcetonitrileCHCN
Acetonitrile

H
H

C
H

www.wunan.com.tw
(02)2705-5066

CH1  Lewis

STRUCTURE

19

H1ee
Cee
1N1ee
1e
acetonitrileLewis

H
H

H
Lewis
e10e
e10e
0e
1e0e
Lewis


[I]

[II]

www.wunan.com.tw
(02)2705-5066

20

[I]1e[II]
1e[II]AcetonitrileLewis

1-1FormicacidHCOOH
Formicacid

O
H

H1ee
1C1ee
Oe1e
1e
 Formic acidLewis

O
H

Lewis
ee
e1e
0e

www.wunan.com.tw
(02)2705-5066

.
., 2014.04

ISBN 978-957-11-7593-5 ()
1.2.
460.31

103005979

5BD2

106 3 3 9 4
(02)2705-5066(02)2706-6100
http://www.wunan.com.tw
wunanwunan.com.tw
0 1 0 6 8 9 5 3

/6
(04)2223-0891(04)2223-3549
/290
(07)2358-702 (07)2350-236

2 0 1 4 4
3 6 0

www.wunan.com.tw
(02)2705-5066