Lecture Two Organic Chemistry

BONDING AND STRUCTURE
Orbital hybridisation of carbon
The concept of hybridisation theory involves the following points :
1. Hybridisation is the mixing of pure orbitals to form new hybrid orbitals which are
equivalent and have definite orientations in space.
2. Only orbitals which lie close together in energy can be used in the construction of hybrid
orbitals.
3. The number of hybrid orbitals always equals the number of component atomic orbitals.
1. sp3 hybridisation
It is formed by one 2s orbital and three 2p orbitals of a carbon atom to give four equivalent
hybrid sp3 orbitals pointing towards the vertices of a regular tetrahedron :
2. sp2 hybridisation
It is formed by one 2s orbital and two 2p orbitals of a carbon atom to give three equivalent
sp2 hybrid orbitals which are pointing towards the vertices of an equilateral triangle:
3. sp hybridisation
It is formed by one 2s orbital and one 2p orbital of a carbon atom to give two equivalent sp
hybrid orbitals of linear structure :
STRUCTURES AND SHAPES OF HYDROCARBONS
1. Saturated hydrocarbons
Hydrocarbons whose molecules contain only single bonds are known as saturated
hydrocarbons. In saturated hydrocarbons the outermost shell electrons of each carbon
atoms have hybridised to form four equivalent sp3 orbitals which are arranged tetrahedrally
about the nucleus. This geometry gives idealized bond angles of 109.5 o.
When an sp3 carbon atom forms bonds, it does so by overlapping each of its four sp 3 orbitals
(each with one electron) with orbitals from other four atoms (each orbital in turn containing
one electron). Therefore it is capable of forming four single bonds. The molecular orbital of
a single bond is symmetrically around the axis passing through the nuclei of two bonded
atoms. It is known as a  bond.
Methane CH4
In methane, each sp3 orbital of carbon overlaps with a 1s orbital of hydrogen. Each of the
resultant sp3-1s molecular orbital is symmetrically around the axis passing through the
nuclei of the carbon and hydrogen atoms. The C-H bonds in methane are  bonds.
Structural formula condensed structural formula 3-dimensional structure (shape)
CH4
Ethane C2H6
Ethane contains two sp3 carbon atoms. These two carbon atoms form a C-C  bond by the
overlap of one sp3 orbital from each carbon. Each carbon atom has three remaining sp 3
orbitals, and each of these overlap with a 1s orbital of a hydrogen atom to form a C-H 
bond.
Structural formula condensed structural formula 3-dimensional structure (shape)

CH3CH3
Propane C3H8 and Butane C4H10
Propane and butane are examples of alkanes that are sometimes called unbranched chain
alkanes. Because of the tetrahedral arrangement of the bond pairs around carbon atoms,
their chains are zigzagged in shape.
Structural formula condensed structural 3-dimensional structure (shape)

formula
CH3CH2CH3
CH3CH2CH2CH3
Cyclohexane C6H12
Cyclohexane is an example of cyclic alkane. If the cyclohexane ring were flat, a serious bond
strain would be resulted and all the hydrogen atoms on the ring would be eclipsed. There
are many shapes that a cyclohexane ring can assume, the most stable one is the ‘chair’ form
with minimum bond strain and all hydrogen atoms staggered.
 Draw the 3-dimensional structure of 2-methylpropane which is a branched chain alkane.
2. Unsaturated hydrocarbons
Hydrocarbons whose molecules contain double bonds or triple bonds are known as
unsaturated hydrocarbons.
Carbon-carbon double bond : the sp2 hybridization
Formation of the C=C bonds
The atomic orbitals of carbon can also hybridise to give three identical sp 2 orbitals arranged
symmetrically in a plane at an angle of 120o to each other, with the remaining electron in a p
orbital at right angles above and below this plane.
Structure and shape of the ethene C2H4 molecule :
In ethene, one of the three sp 2 orbitals overlaps with an sp 2 orbital of a second carbon atom
to form a  bond. The other sp2 orbitals of the two carbon atoms each overlaps with the 1s
orbital of a hydrogen atom to form four  bonds. The 2p orbitals of the carbon atoms
overlap above and below the plane to form a  bond. A  bond is formed by lateral overlap
of the p orbitals and has a plane of symmetry.
A C=C double bond consists of a  bond and a  bond. A  bond is stronger than a  bond
as it is formed between the lines of centres of the bonding atoms and greater orbital
overlap is possible.
Shape of the ethene molecule :
 Draw the 3-dimensional structure of propene and indicate the  and  bonds in the
molecule.
Carbon-carbon triple bond : the sp hybridization
Formation of the CC bonds
The hybrid orbitals formed from the 2s and one of the 2p orbitals of carbon atom consists of
two identical collinear sp orbitals with lobes directed in opposite directions on either side of
the nucleus. The two remaining unpaired electrons are in 2p orbitals at right angles to each
other.
Structure and shape of the ethyne C2H2 molecule :
In the ethyne C2H2 molecule, one of the two sp orbitals overlap with an sp orbital of a
second carbon atom to form a  bond, while the two remaining sp orbitals(one on each
carbon atom) form  bonds with hydrogen atoms. The unhybridised 2p orbitals overlap
laterally and two  bonds are formed in planes at right angles above, below and on either
side of the linear molecule.
A CC triple bond consists of a  bond and two  bonds. These  bonds draw the carbon
atoms closer together, making the CC bond both shorter and stronger than the carbon-
carbon double and single bonds.
 The following two compounds have the same molecular formula C 5H8 but different
structures :
Give the hybridisation states of all carbon atoms and draw the 3-dimensional structures for
both compounds.

Lecture Two Organic Chemistry

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BONDING AND STRUCTURE

Orbital hybridisation of carbon

The concept of hybridisation theory involves the following points :

STRUCTURES AND SHAPES OF HYDROCARBONS

Structural formula condensed structural formula 3-dimensional structure (shape)

Structural formula condensed structural formula 3-dimensional structure (shape)

Propane C3H8 and Butane C4H10

Structural formula condensed structural 3-dimensional structure (shape)

 Draw the 3-dimensional structure of 2-methylpropane which is a branched chain alkane.

Carbon-carbon double bond : the sp2 hybridization

Formation of the C=C bonds

Structure and shape of the ethene C2H4 molecule :

Shape of the ethene molecule :

Carbon-carbon triple bond : the sp hybridization

Formation of the CC bonds

Structure and shape of the ethyne C2H2 molecule :

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