HYBRIDIZATION AND RESONANCE

SHAPES OF SIMPLE
ORGANIC MOLECULES

Types of Atomic Orbital

present in carbon that
contain electrons
1s orbital- spherical

2s orbital- spherical

2p orbitals- lobes

P orbital

There are three p

orbitals- 2px, 2py and
2pz

P orbital

Bonding
The ground state configuration of
carbon is unsuitable for bonding.

2px

2py

2pz

Energy
2s

1s
Ground State of Carbon

In the ground state carbon can

only form three bonds (unequal
length and strength).
For correct bonding to occur
some changes have to be made in
the orbitals.

O rbitalChanges-Excitation

2px

2py

2pz
2px

Energy
2s

2py

2pz

Energy
2s

1s

1s
Ground State of Carbon

Excited State of Carbon

O rbitalChanges-H ybridization
sp 3

2px

2py

2pz

Energy

Energy

sp3

2s
1s
sp3 Hybridized State of Carbon

1s
Excited State of Carbon

sp 3 hybridized orbital

sp 3 hybridized orbital

S and p orbitals

Sp3 orbitals

Bonding in Methane
(CH4)
0 Overlap of s and

sp3 orbitals form

sigma () bond

0 Carbon atom is

sp3 hybridized
0 Bonds are formed by

overlapping of the 1s
orbitals of four
hydrogen atoms with
the sp3 orbitals of the
carbon atom

Methane has 4
bonds

Note that each bond contains 2

electrons: 1 from s orbital of hydrogen
1 from sp3 orbital of carbon

Bonding in Ethene
(C2H4)

0 Ethene contains a double bond

0 In carbon of double bond there are three

sp2 hybrid orbitals and one unused p orbital

0 Each carbon in the double bond is sp2
hybridised
0 Unused p orbital overlaps above and below the
plane to form a pi () bond

http://www.citycollegiate.com/hybridizat
ion2.htm

Bonding in Ethyne
(C2H2)

0 Ethyne contains a triple bond

0 In carbon of triple bond there are two sp hybrid

orbitals and two unused p orbital

0 Each carbon in the triple bond is sp hybridised
0 The two unused p orbitals overlap above and
below the plane to form two pi () bonds

 The triple bond consists of one sigma

bond and two pi bonds
The geometry around each carbon is
linear with a bond angle of 180o
http://pages.towson.edu/ladon/carbon.
html

Benzene
Six

carbon atoms in a ring

Shows

resonance hybridisation

Hexagonal

in shape - at each apex there is a

carbon bonded to a hydrogen

Each

carbon is bonded to three other atoms; a

hydrogen and two other carbon atoms

Each
Each

carbon uses sp2 hybrid orbitals

carbon contains a pure p orbital

perpendicular to the plane of the ring

Benzene
Each

unhybridized p orbital
overlaps with two other p
orbitals, one on each of the two
neighbouring carbon atoms

large circular pi-type bond is

formed above and below the
plane

Electrons

are delocalized in the

benzene ring

Benzene
Overlapping of p orbitals

Benzene

Benzene
Canonical forms

Benzene
Hybridized structure