Organic Chemistry

INSPIRING GREATNESS
Carbon
• The chemistry of carbon compounds.
• Carbon has the ability to exist in a number of
geometries
and to bond to any atom type.
• Without this property, large biomolecules such
as proteins, lipids, carbohydrates, and nucleic
acids could not form.
Carbon
Group 14, atomic number, Z = 6
 Electron configuration:
1s 2 2s 2 2p 2

 Multiple bonds – carbon can readily form multiple

bonds, ie. double and triple bonds, both with itself
and other elements

H H H H
H C C H C C H C C H
H H H H
Ethane Ethene Ethyne

3
Valence Bond Theory
A covalent bond is formed by the overlap of
atomic orbitals

Requires that each orbital involved in the covalent bond

contains only ONE electron

4
 VBT - Carbon
Problem:
According to the ground state electron configuration,
carbon only has TWO unpaired electrons, ∴ can only
form TWO covalent bonds according to VBT.

Ground state
2s 2p

Be

1s 2s
Hybridisation
A mathematical process derived to adapt VBT to explain
the bonding that is actually observed in molecules.

Eg. Carbon form s 4 bonds, m ethane, CH 4

The new orbitals are called hybrid orbitals
Hybridization: process of mixing orbitals to form new,
identical orbitals

There are three hybridization states and geometries found

in organic compounds:

sp 3 - tetrahedral sp 2- trigonal planar sp - l inear

 Sigma (δ) and pi (Π) bonds

Head-on overlap - Sigma (δ) Sideway overlap- pi (Π)

 Carbon almost always forms FOUR bonds!
In its excited state, carbon has four unpaired electrons

BUT - one bond would be different from the other 3!

sp 3 Hybridisation
 Bonding in Methane

• The bond formed from the

overlap of an sp3 orbital and a
1s orbital is an example of a
sigma (σ) bond.

• All purely single bonds are

sigma bonds.
Molecular Geometry – tetrahedral
Bond Angle – 109.5o
10
sp 2 Hybridisation of Carbon
Ethene, C2H4 H H
C
H

Hybridised
Unhybridised p -orbitals are orbitals form
used for π-bonding ONLY σ-bonds

11
sp 2 Hybridisation of Carbon
 sp 2 Hybridisation of Carbon

Molecular Geometry – trigonal planar

Bond Angle – 120o
12
A model for the bonding molecular orbitals of ethene formed from two sp2-hybridized carbon
atoms and four hydrogen atoms.
sp Hybridisation of Carbon
Ethyne, C2H2 H C C H

Hybridised
Unhybridised p -orbitals are
orbitals form
used for π-bonding ONLY σ-bonds
A process for deriving sp-hybridized carbon atoms.
 sp Hybridization of Carbon
Ethyne C2H2

Molecular Geometry – linear

Bond Angle – 180o

14
Bond angles and bond lengths of ethyne, ethene and ethane.

Bond length: sp hybrids < sp2 hybrids < sp3 hybrids for both C-C and C-H bonds.

Bond strength: ??
Oxygen

Hybridization
sp3

2s 2p

2p
Hybridization

2p sp2
2s
Exercise
Find the hybridization and geometric angle
of nitrogen:

1. NH3

2. HC N
Hybridisation
Summary

Hybridisation # Bonds Molecular

Bond Angle E.g.
State σ Bonds π Bonds Geometry

sp3 4 0 109.5o Tetrahedral C-C

C=C
sp2 3 1 120o Trigonal planar
C=O
CΞC
sp 2 2 180o Linear
CΞN

17
 Examples
Indicate the hybridization for carbons 1 – 10 and
their respective geometry. Include bond angles in
your answer. Br
H H
C O
H 1 C Cl
2 C 3 C
H C 9 C
C C 8 10 N
O 4 C 7
6
F H
H

Hybridization Geometry Bond angles

Carbon 1, 2 and 6:
Carbon 3, 4 and 9:
Carbon 7, 8 and 10:
18
 Examples
Indicate the hybridization for carbons 1 – 10 and
their respective geometry. Include bond angles in
your answer. Br
H H
C O
H 1 C Cl
2 C 3 C
H C 9 C
C C 8 10 N
O 4 C 7
6
F H
H

Hybridization Geometry Bond angles

Carbon 1, 2 and 6: sp3 Tetrahedral 109.5 deg
Carbon 3, 4 and 9: sp2 Trigonal 120 deg
Carbon 7, 8 and 10: sp Linear 180 deg
18