Hybridization of
carbon
The Carbon
• Organic chemistry is the chemistry of compounds that contain the element
carbon.
• The name “organic” reflect the fact that organic molecules are derived from
living organisms.
• The element, carbon, is one of the most versatile elements on the periodic
table in terms of the number of compounds it may form.
• It may form virtually an infinite number of compounds.
• This is largely due to the types of bonds it can form and the number of
different elements it can join in bonding.
• Carbon may form single, double and triple bonds.
• Formation of these bonds involve hybridization of carbon.
Carbon’s Hybridization
• Note: A hybrid occurs when two things are combined and the result
has characteristics of both
• The carbon atom has four valence electrons with the electron configuration
of 1s22s22p2
• You may expect the two unpaired p electrons to bond with other atoms
and the two paired s electrons to remain as a lone pair
• However, carbon undergoes hybridization, a process in which atomic
orbitals mix and form new, identical, hybrid orbitals.
sp3 Hybrid Orbitals
• Carbon has two core electrons, plus four valence electrons.
• To fill atomic orbitals in the most stable arrangement, electrons are placed
in the orbitals of lowest energy.
• For carbon, this places two in the 2s orbital and one each in 2p orbitals.
• Note: The lowest energy arrangement of electrons for an atom is called its
ground state.
• An electron is promoted from a 2s to a vacant 2p orbital forming four
unpaired electrons for bonding.
• This process requires energy because it moves an electron to a higher
energy orbital.
• This higher energy electron configuration is called an electronically excited
state.
• Atoms like carbon do not use pure s and pure p orbitals in forming bonds
• The 2s and 2p orbitals of carbon atoms combine (or mix) to form four
degenerate orbitals called hybrid orbitals (i.e. orbitals of equal energy)
• Hybridization is the combination of two or more atomic orbitals to form the
same number of hybrid orbitals, each having the same shape and energy.
• The hybrid orbitals formed from one s orbital and three p orbitals are
called sp3 orbitals.
• The mixing of a spherical 2s orbital and three dumbbell shaped 2p
orbitals together produces four hybrid orbitals, each having one large
lobe and one small lobe.
• The sp3 orbitals formed are all half-filled, with the electron far more likely
to be found in the larger lobe.
• Note that each hybrid orbital contains one electron that it can share with
another atom, giving carbon 4 bonding sites.
• The hybrid orbital is called an sp3 orbital because the four orbitals form
from one s and three p orbitals.
• Since electrons repel each other, the four sp3 hybridised orbitals
surrounding a central carbon atom result in a familiar tetrahedral shape,
with a maximum possible angle between each orbital of 109.5°.
Bonding in CH4
• Each bond in CH4 is formed by overlap of an sp3 hybrid orbital of carbon
with a 1s orbital of hydrogen.
• These four bonds point to the corners of a tetrahedron.
Bonding in ethane, CH3CH3
• Carbon-to-carbon single bonds in alkanes result from overlapping sp3
orbitals forming σ bonds.
• σ bonds are covalent bonds formed by end-on overlap of two atomic
orbitals and since σ bonds must lie along the line joining both atoms, there
will be free rotation around these orbitals.
H H
C C
H σ bond H
H H
Other Hybridization Patterns
• One 2s orbital and three 2p orbitals form four sp3 hybrid orbitals.
• One 2s orbital and two 2p orbitals form three sp2 hybrid orbitals.
• One 2s orbital and one 2p orbital form two sp hybrid orbitals.
