1.

Structure and Bonding in

Organic Chemistry
Electron Configurations
Lewis Dot Structures
Hybridization
Orbital depictions
Edited by: Dr. Nadeem Sadiq Sheikh
Department of Chemistry, College of Science
King Faisal University, Saudi Arabia
https://sites.google.com/site/243chem

Organic Chemists Periodic Table

Molecular Model of Aspirin

Nucleus is a Tiny Fraction of

the Volume of an Atom

Bonding in H2
Sigma (Bond

Electron Configurations

Ground State Electron

Configurations

px, py, pz

Electron Configuration of Carbon

Lewis Dot Structure of

Methane
carbon - 4 valence e

.
.C.
.

1s22s22p2

hydrogen - 1 valence e

H.
1s

All Have the Same Geometry

All Have 4 Regions of Electron Density

Tetrahderal Geometry

Methane Representations

In Ground State
2 bonding sites, 1 lone pair
H
CH4

2p

H
H

2s

ground state

sp3 Hybridization
4 Regions of electron Density

link

H
CH4

2s

2s

2p

2p

ground state

hybridize
x

excited state

4 identical sp3 orbitals

4 sigma bonds requires 4 hybrid orbital
tetrahedral geometry
4
sp3

Hybridization of 1 s and 3 p
3
Orbitals sp

sp is Tetrahedral Geometry
Methane
3

Ammonia
Tetrahedral Geometry
Pyramidal Shape

Orbital Depiction of Ethane,

C2H6 , the bond

Depictions of 2-Methylbutane

Bonding Characteristics of Period 2

Elements

Saturated with Hydrogen

A Model of a Saturated Hydrocarbon

sp2 Hybridization
3 Regions of Electron Density
CH2=CH2
H
C

2s

2s

2p

2p

H
H

hybridize
x

excited state

ground state

pz

3 identical sp2 orbitals

3 sigma bonds requires 3 hybrid orbitals
trigonal planar geometry

sp2 pz

Hybridization of 1 s and 2 p
Orbitals sp2

An sp2 Hybridized Atom

Ethylene CH2=CH2

Views of Ethylene, C2H4

Ethylene

Formaldehyde

sp Hybridization
2 Regions of Electron Density
H

2p

C H

2s

2p
2s

ground state

hybridize
x

excited state

py

pz

2 identical sp orbitals
2 sigma bonds requires 2 hybrid orbitals
linear geometry
2

The sp Orbital

Acetylene, C2H2,
1 bond
2 perpendicular bonds

Drawing Structures
H
H

C
H

H
C
H

H
C
H

H
C
H

Butane, C4H10
CH3CH2CH2CH3

H C C C
H
H
H
C
H
H
H
Methylpropane, C 4H10
CH3CH(CH3)CH3

Octane Representations
C8H18 is molecular formula but there are 18 possible structural isomers
H

H H H H H H
H
C
C
C
C
H
C
C
C
C
H
H H H HH H
HH
Lewis structure

CH3CH2CH2CH2CH2CH2CH2CH3
CH3(CH2)6CH3
condensed structural formula

Condensed
Formulas

Line-Angle Structures are

Often Used as a Short-hand
H

H H H H H H
H
C
C
C
C
H
C
C
C
C
H
H H H HH H
HH
Lewis structure

Line-angle or "zig-zag" structures

Line-Angle Structures
C12H26

H
H

H
H
H

C
H H

H
H

H
H

C
C

H
H

C
H

C
H

C
H
H

H
H

H H

H
H
H

H
H

H
H

At the end of every line and at the intersection of any lines

there is a carbon atom with 4 bonds. Hydrogen atoms
are mentally supplied to fill the valency to 4.
H
H

H
H

H
H
H

H H

H
H
H

H
H

H
H

Line-Angle structure
Superimposed on Lewis Structure
H
H

H
H
H

C
H H

H
H

H
H

C
H

C
C

C
H

C
H

C
H
H

H
H

Double Bonds are Shown

Depictions of trans 2-pentene
H
H
H

C
C
H

C H
H

H H
Lewis Structure

CH3

H
C

CH2CH3

condensed structural formula

line-angle or zig-zag structure

For Cyclic Structures, Draw the

Corresponding Polygon
Cyclohexane
H H
H
H
C
C H
H C
H C
C H
C
H
H
H
H

Drawing Clear Structures

Benzene can be drawn as one of

two resonance structures
H
H
H

C
C

C
C
H

H
C
C

H
H

H
H

C
C

C
C
H

C
C

H
H

Some Line-Angle Structures