BASIC ORGANIC CHEMISTRY

(CHM 203)

DR O. T. ASEKUN

& DR A. ABAYOMI
 Bonding in Carbon
• Organic chemistry is the chemistry of the compounds of
carbon and hydrogen.
• The compounds may also include oxygen, nitrogen, sulphur
and halogens.
• Carbon is the sixth element on the periodic table with an
atomic number of 6.
• The carbon atom can covalently bond to other carbon atoms
(catenation) and to atoms of other elements in a wide variety
of ways.
• Catenation is peculiar to the Group IV elements which carbon
belongs to.
• It decreases down the group with carbon having the highest
ability to catenate.
Bonding in Carbon
• The location of the bonding electrons in carbon is best
described by the Quantum theory.

• The theory describes the most probable location of an electron

(at a specific energy level) around a nucleus.

• The energy level called “shell” of an atom is subdivided into

atomic orbital.

• There are different types of orbitals including;

 sharp
 principal
 diffuse
 fundamental
• The s and p orbitals are the more important in the
formation of organic molecules
The s - orbital
• It has a spherical shape with the nucleus of the atom
located in the centre.
• The lowest energy electron occupies the 1s atomic
orbital.
• Each orbital can hold a maximum of two electrons.
The p-orbital
• The 2p electrons are the next higher orbital in energy level to the
2s electrons.

• The p orbital is further split into three sub atomic orbitals; p x, py

and pz.

• The three sub orbitals are called degenerate orbitals and have a
dumb-bell shape.

• Their orientation in space is such that they are perpendicular to

one another.

• They are equivalent in shape and in distance from the nucleus of

the atom.
Hybrid Atomic Orbital of Carbon
• The electronic configuration of carbon in the ground
state is 1s2 2s2 2p2 .
• Thus, there are four atomic orbitals in the second
energy level: 2s, 2px, 2py and 2pz.
• Prior to bonding, the four orbitals are mixed or
hybridized in one of three different forms including;
I. sp3 hybridization
II. sp2 hybridization
III. sp hybridization
sp3 Hybridization
• This involves the mixing of one atomic s-orbital and
all the three p-orbitals.
• Four equivalent hybrid orbitals, sp3, are formed.
• The four orbitals are spatially oriented toward the
corners of a regular tetrahedron.
• In methane (CH4) for example, the carbon atom is at the centre
of the tetrahedron and hydrogen atoms situated in the corners.

• Each C-H bond is formed by the overlap of the sp3 hybrid

orbital of C and the s orbital of H (sigma bond). The bond angle
is 109.28o

• Alkanes generally use sp3 hybridization.

H (sp3 – s)
109.28o
bond
C
H H

H
sp2 Hybridization
• This involves the mathematical mixing of the 2s orbital
with two 2p (2px and 2py) orbitals.
• The third 2pz orbital remains unhybridized and is
perpendicularly oriented with the hybrid sp 2 orbital
formed.
• The three sp2 orbitals formed lie in a plane at angles of
120o to each other.
• Example of sp2 hybidization in carbon could be seen
in ethene (C2H4).

• The shape of the sp2 hybridized carbon is trigonal.

• In ethene, two bonds are formed between the

carbons; hybridized sp2 – sp2 bond (sigma) and
unhybridized sp2 – sp2 bond (pi).
sp Hybridization
• This is hybridization to form two equivalent hybrid orbitals.
• It involves mixing of the 2s orbital with one of the three 2p
orbitals.
• The two hybrid orbitals formed lie on the same plane with
an angle of 180o .
• The two remaining unhybridized 2p orbitals remains
perpendicular to the hybridized orbitals.
• sp hybridization is widely seen in alkynes.
• The shape of the molecule with this type of
hybridization is linear.
• In ethyne for example, the two unhybridized 2py and
2pz orbitals of one carbon overlap with those of the
other carbon to from two pi bonds.
Hybridized Orbital Character

Hybridization % p- % Relative
Character s-Character Overlapping
Power
s (pure) - 100 1.00

p (pure) 100 - 1.72

sp 50 50 1.93

sp2 66.7 33.3 1.99

sp3 75 25 2.00