HYBRIDISATION
sp3 hybridisation
2px 2py 2pz 2p 2px 2py 2pz 2p
Promotion of one 2s electron
E E
2s 2s
1s 1s
Carbon in its ground state
Hybridisation of one 2s orbital and
three 2p orbitals
four sp3 orbitals
1s
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• Hybridisation and promotion of one of the 2s electrons requires
energy (402 kJ/mole) but this is offset by the energy regained by the
concurrent formation of chemical bonds.
• The four sp3 orbitals of carbon point towards the
corners of a regular tetrahedron - position of least resistance.
• Covalent bonds between carbon and hydrogen in methane, like the
H-H covalent bond, are sigma (σ) bonds.
• Used in all single bonded compounds of carbon
• Carbons in single bonded systems have 4 σ-bonds and are
tetrahedral.
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sp2 hybridisation
2px 2py 2pz 2p 2px 2py 2pz 2p
Promotion of one 2s electron
E E
2s 2s
1s 1s
Hybridisation of one 2s orbital and
two 2p orbitals
2pz
three sp2 hybridised orbitals
E
1s
H H
Ethene
H H
bond bond
Image courtesy of socratic.org
MO diagram for carbon-carbon
double bond
*
unfilled antibonding
orbitals
carbon carbon
2p 2p
filled bonding C-C
orbital
sp2 sp2
2 x sp2 used in 2 x sp2 used in
bonds to 2 x H or R bonds to 2 x H or R
filled bonding C-C
orbital
Adapted from Organic Chemistry, Clayden, Greaves and Warren, OUP, 2nd edition.
• sp2 hybrid orbitals are utilised in the formation of molecules
containing carbon-carbon double bonds e.g. ethylene CH2=CH2
• The two carbons of ethylene (or ethene) are joined by a sigma bond
formed by the overlap of one of the sp2 hybrid orbitals of each
carbon.
• The other sp2 hybrid orbitals overlap with the 1s orbitals of the four
hydrogen atoms.
• Since p-orbitals lie side by side their ends cannot overlap as they do
in σ-bond formation.
• Their sides overlap forming a π-bond.
• A carbon bonded to three other atoms is in the sp2 hybrid state.
• In stable state, the p orbitals (carbon) must overlap with the p
orbitals of an adjacent atom (not necessarily carbon).
sp hybridisation
2px 2py 2pz 2p 2px 2py 2pz 2p
Promotion of one 2s electron
E E
2s 2s
1s 1s
Hybridisation of one 2s orbital and
one 2p orbital
2pz 2py
two sp hybridised orbitals
E
1s
H C C H
Image courtesy of socratic.org
Consequences of hybridisation
• When carbon is bonded to four other atoms, four
equivalent sp3 orbitals are used; the carbon is
tetrahedral.
• When carbon is bonded to three other atoms, three
equivalent sp2 orbitals are used; the carbon is trigonal
and planar.
• When carbon is bonded to two other atoms, two
equivalent sp orbitals are used; the carbon is linear.
Bond length
• Is related to the ‘s’ character of the bonds.
• The greater the proportion of ‘s’ character the shorter the
bond length.
• The greater the proportion of ‘s’ character the lower the
energy.
• The sp orbital contains most ‘s’ character; it is closer to
the nucleus and forms shorter (120 pm, 839 kJ.mol-1)
and stronger bonds.
• The sp3 orbital (154 pm, 348 kJ.mol-1) is the longest and
weakest.
• The sp2 orbital is intermediate (134 pm, 614 kJ.mol-1).
Bonds to other elements
C=O double bond
Oxygen's electronic configuration:
2pz
2px 2py 2pz 2p Hybridisation of one 2s
orbital and two 2p orbitals
E E three sp2 hybridised
2s orbitals
1s 1s
H
H
C + O C O
H
H
lone pairs
bond
carbon and oxygen both sp2 hybridised C-O bond
H
C O
H
