Hybridisation in Carbon

HYBRIDISATION IN CARBON
Valence
electrons

1-18
Hybrid Orbitals
 Hybridization of orbitals
• the combination of two or more atomic orbitals
forms a new set of atomic orbitals, called hybrid
orbitals

 There are three(3) types of hybrid orbitals

• sp3 (one s orbital + three p orbitals)

• sp2 (one s orbital + two p orbitals)
• sp (one s orbital + one p orbital)

1-19
Types of Bonds
 Overlap of hybrid orbitals can form two types
of bonds depending on the geometry of
overlap
 bonds are formed by “direct” overlap
 bonds are formed by “parallel” overlap

1-20
 sp3 Hybridisation
s pxpypz

Valence electrons
of Carbon

orbitals sp3 Hybrid orbitals

The four orbitals (an s and three p’s) combine or

HYBRIDISE to give four new orbitals. All four orbitals
are equivalent.
1-21
sp3 Hybridisation

In ALKANES, the four sp3 orbitals repel each other

into a tetrahedral arrangement.

. .
.
1-22
sp3 Hybrid Orbitals
 each sp3 hybrid orbital has two lobes of unequal
size
 the four sp3 hybrid orbitals are directed toward the
corners of a regular tetrahedron at angles of 109.5°

1-23
sp3 Hybrid Orbitals
orbital overlap picture of methane

1-24
 hybridisation
s pxpypz

Valence electrons

sp2 orbitals p orbital

Only three orbitals (an s and two p’s) HYBRIDISE

to give three new orbitals. All three orbitals are
equivalent. The remaining 2p orbital is unchanged.

1-25
 hybridisation three sp2 orbitals

p orbital

In ALKENES, the three sp2 orbitals repel each other

into a planar arrangement and the 2p orbital lies at
right angles to them
1-26
Bond formation in alkenes

Covalent bonds are formed by overlap of orbitals

An sp2 orbital from each carbon overlaps to form a

single C-C bond

The resulting bond is called a SIGMA (s) bond.

1-27
Bond formation in alkenes

The two 2p orbitals also overlap to form a

second bond. This is known as a pi () bond.

1-28
Bond formation in alkenes

To complete the structure of ethene, the remaining sp2

orbitals overlap with four hydrogen 1s orbitals to
form four C-H bonds.
1-29
Bonding in Ethene (Ethylene)

1-30
 The Structure of Ethene (Ethylene) : sp2 Hybridization
 Ethene (C2H4) contains a carbon-carbon double bond and is in the
class of organic compounds called alkenes
 Another example of the alkenes is propene

 The geometry around each carbon is called trigonal planar

 All atoms directly connected to each carbon are in a plane
 The bonds point towards the corners of a regular triangle
 The bond angle are approximately 120o

Chapter 1 31
 sp HYBRIDISATION

The electronic configuration of a carbon atom is 1s22s22p2

2s22p2 2s12p3 x sp 2 2p
promotion hybridization

Valence electrons

sp orbitals
unhybridised

One s orbital combines with one p orbital leaving two p orbitals

sp hybridized orbital has 50% s and 50% p character

1-32
sp Hybrid Orbitals
• two lobes of unequal size at an angle of 180°
• the unhybridized 2p orbitals are perpendicular to each
other and to the line created by the axes of the two sp
hybrid orbitals

sp hybrids

1-33
Bonding in Acetylene, C2H2

1-34
Hybrid Orbitals

Groups Orbital Predicted Types of

Bonded Hybrid- Bond Bonds
to Carbon ization Angles to Carbon Example Name
HH
4 sp3 109.5° 4 sigma bonds H-C-C-H Ethane
HH

2 3 sigma bonds H H
2 sp 120° C C Ethylene
and 1 pi bond
H H

2 sp 180° 2 sigma bonds

H-C C-H Acetylene
and 2 pi bonds

1-35
 VSEPR
Valence Shell Electron Pair Repulsion Theory
 Based on the twin concepts that
• atoms are surrounded by regions of electron density
• regions of electron density repel each other
H
4 regions of e- density

:
C N
(tetrahedral, 109.5°) H H H O
H H H H
H

3 regions of e- density H H H H H

:
(trigonal planar, 120°) C C C O C N

:
H H H H

2 regions of e- density
: :

O C O H C C H H C N
(linear, 180°)
:

1-36
 Resonance Structures

O3 can be drawn in 2 ways:

O O
O O O O
I II

These are two different reasonable Lewis structures for

the same molecule.

Neither structure depicts O3 accurately, because in reality

the O-O bonds are identical in length and energy.

10-37
 Resonance Structures
The structure of O3 is shown more correctly using both
Lewis structures, called resonance structures.
A two-headed resonance arrow is placed between them.

O O
O B O O B O
A C A C
I II

Resonance structures have the same relative placement

of atoms but different locations of bonding and lone
electron pairs.

10-38
 The Resonance Hybrid

A species like O3, which can be depicted by more than

one valid Lewis structure, is called a resonance hybrid.

Resonance forms are not real bonding depictions.

O3 does not change back and forth between its two
resonance forms.

The real structure of a resonance hybrid is an average

of its contributing resonance forms.

10-39
 A mule is a genetic mix, a hybrid, of a horse and a donkey. It is not
a horse one instant and a donkey the next. Likewise, a resonance
hybrid has a single structure although it retains characteristics of
its resonance forms.

10-40
 Electron Delocalization

Lewis structures depict electrons as localized either on an

individual atom (lone pairs) or in a bond between two atoms
(shared pair).

In a resonance hybrid, electrons are delocalized: their

density is “spread” over a few adjacent atoms.

O
O O
Dotted lines are used to show
delocalized electrons.

10-41
 Resonance
 The real carbonate ion is not represented by any of the
structures 1,2 or 3

 Experimentally carbonate is known not to have two

carbon-oxygen single bonds and one double bond; all
bonds are equal in length and the charge is spread 42
equally over all three oxygens
 The real carbonate ion can be represented by a drawing
in which partial double bonds to the oxygens are shown
and partial negative charge exists on each oxygen
 The real structure is a resonance hybrid or mixture of
all three Lewis structures
 Double headed arrows are used to show that the three
Lewis structures are resonance contributors to the true
structure

The real carbonate ion

Not real but usually drawn to
– a resonance hybrid
keep track of electrons
 The energy of the actual molecule is lower than
the energy of any single contributing form
 The lowering of energy is called resonance stabilization
 Equivalent resonance forms make equal
contributions to the structure of the real molecule
 Structures with equivalent resonance forms tend to be
greatly stabilized
 Example: The two resonance forms of benzene
contribute equally and greatly stabilize it
 The shape of benzene
 Benzene is a planar regular hexagon, with bond angles of
120°.

The ring system of pi electrons forms because of the

delocalisation of the electrons in the pi bonds.