Structure and Bonding in
Organic Chemistry
Learning Objectives
In this topic students will learn about:
• Electron Configurations
• Lewis Dot Structures
• Hybridization
• Orbital depictions
Organic Chemist’s Periodic Table
S BLOCK
P BLOCK
D
BLOCK
▪ The nucleus contains positively charged protons and
uncharged neutrons.
▪ The electron cloud is composed of negatively charged
electrons.
s orbital, p orbital
• An s orbital has a sphere of electron density and is lower
in energy than the other orbitals of the same shell.
• A p orbital has a dumbbell shape and contains a node of
electron density at the nucleus. It is higher in energy than
an s orbital.
6
2s 2px 2py 2pz
Electron Configuration of Atoms
Aufbau Principle:
• orbitals fill in order of increasing energy from lowest
energy to highest energy
Pauli Exclusion Principle:
• only two electrons can occupy an orbital and their
spins must be paired
Hund’s Rule:
• when orbitals of equal energy are available but there
are not enough electrons to fill all of them, one
electron is added to each orbital before a second
electron is added to any one of them
s orbital, p orbital
Since there is only one orbital in the first shell, and each
orbital can hold a maximum of two electrons, there are
two elements in the first row, H and He.
Each element in the second row of the periodic table has
four orbitals available to accept additional electrons: one
2s orbital, and three 2p orbitals.
Bonding in H2
Sigma (s) Bond
Ground State Electron
Configurations
Electron Configuration of
Carbon
Lewis Dot Structure of Methane
carbon - 4 valence e hydrogen - 1 valence e
.
.C.
. H.
1s22s22p2 1s
Hybridization
❖ The atoms like carbon do not use pure s and pure p
orbitals in forming bonds. Instead, atoms use a set of
new orbitals called hybrid orbitals.
❖ 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.
6C
1s2 2s2 2p2
Ground state of C 1s2 2s2 sp2
s px py pz
Promote electron (excited state) 2s12p3
s px py pz
Hybridize (excited state) sp3 sp3 sp3 sp3
sp3 sp3 sp3 sp3
Four sp3 orbitals of equal length, energy and in tetrahedral shape and
form four σ bonds
Shape and Orientation of sp3
Hybrid 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 four hybrid orbitals are oriented towards the corners of a
tetrahedron, and form four equivalent bonds.
17
sp3 + sp3 + sp3 + sp3
Because we combined the s orbital and all three p orbitals,
we call these new orbitals “sp3 orbitals”. There are four of
them, each pointing towards a corner of a tetrahedron,
exactly where we want them.
Bonding Using sp3 Hybrid
Orbitals
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 CH4 using sp3 hybrid orbitals
SP2 Hybridization
Unhybridized
Forms σ (sigma) bonds Orbital
Forms π (pi) bonds
• One 2s orbital and two 2p orbitals form three sp2 hybrid
orbitals.
22
When an s and two p orbitals are mixed to form a set of
three sp2 orbitals, one p orbital remains unchanged and is
perpendicular to the plane of the hybrid orbitals.
Ethylene CH2=CH2
Views of Ethylene, C2H4
Formaldehyde
Acetylene, C2H2,
1 s bond
2 perpendicular p bonds
Other Hybridization Patterns
• To determine the hybridization of an atom in a molecule,
we count the number of groups around the atom.
• The number of groups (atoms and nonbonded electron
pairs) corresponds to the number of atomic orbitals that
must be hybridized to form the hybrid orbitals.
29
Condensed Formulas
Textbooks required
1. McMurry, John, Organic Chemistry, 6th edition, 2004,
Thomson Learning Inc. USA
2. Brown, William H., Introduction to Organic Chemistry, 1st
edition, Saunders College Publishing
Questions
1. The valency of carbon is
a) 1
b) 2
c) 3
d) *4
2. The no. of electrons in first energy level
a) 3
b) *2
c) 5
d) 6
3. The electronic configuration of carbon is
a) *1s22s22p2
b) 1s22s22p1
c) 1s22s22p3
Cont….
d) 1s22s2
4. The electronic configuration of carbon in excited state is
a) 1s22s22p2
b) *1s22s12p3
c) 1s22s22p3
d) 1s22s22s1
5. The hydridized orbitals forms
a) Pi bonds
b) *Sigma bonds
c) Dative bonds
d) Coordinate bonds
Thank you
