CHM004:

ORGANIC
CHEMISTRY
 LEARNING OBJECTIVES
At the end of the lesson, the students should
be able to;
 Define organic compounds
 State the properties of organic compounds
 Represent organic compounds using different
formulae
 Define hybridization
 State the types of hybridization and give
examples of each.
 Organic Chemistry
• Organic chemistry can be defined as the study of organic
compounds (i.e. the structure, properties and reactions of
organic compounds).
• Organic compounds are a class of molecular compounds that
are composed of carbon and hydrogen and a few other
elements, including nitrogen, oxygen, and sulfur.
• The chemistry of carbon is unique and complex because
carbon frequently bonds to itself to form chain, branched, and
ring structures. This process is called catenation.
• Also, the tetravalent nature of the carbon atoms allows
branched chains to occur, and the attachment of other atoms,
increasing further the number of structures possible and the
seemingly unlimited number of compounds.
PROPERTIES OF ORGANIC
COMPOUNDS
• Organic compounds are mostly non-polar (unless a more
electronegative atom is present).
• They have low melting and boiling points due to the
relatively weak attraction between molecules.
• They are insoluble in water (unless a polar group is present)
• Organic compounds are kinetically stable as the carbon
atoms form stable covalent bonds between themselves.
Most organic compounds do not react with oxygen unless
heated to quite a high temperature-the ignition point. This
low rate of reaction at room temperature is a result of the
high activation energy that many organic reactions possess,
which in turn is due to the strong bonds that carbon forms
to itself and to other elements.
SHAPES OF ORGANIC
MOLECULES
• All organic structures possess a three-dimensional structure where
the various atoms are fixed in their relative positions.
• The shapes of organic molecules ultimately depend on bond lengths
and bond angles.
• In each of the molecules (carbon dioxide and hydrogen
cyanide) in the first row below, the three atoms are
collinear (they all lie on the same straight line).
• In the molecule of ethane, in the second row, all six atoms
are coplanar (they all lie in the same plane). Ethene is a
‘two-dimensional’ molecule.
• Methane, however, is a three-dimensional molecule, and
its shape cannot be easily represented on a two-
dimensional page. Stereochemical formula is used to
show the three-dimensional structure.
• The dashed line represents a bond behind the plane of
the paper, the solid wedge represents a bond coming out
in front of the plane of the paper, and ordinary lines
represents bonds that are in the plane of the paper.
 FORMULAE USED TO REPRESENT
ORGANIC COMPOUNDS
• There are six types of formulae that are used to represent organic
compounds.

1. The empirical formula: This gives the simplest ratios in which the
elements contained in a compound are combined. E.g., the empirical
formula for ethanoic acid is CH2O while that of iso-octane (2,2,4
trimethylpentane) is C4H9.
2. The molecular formula: This tells us the actual number of atoms of each
element present in a molecule of the compound. E.g., the molecular
formula of ethanoic acid and iso-octane are C2H4O2 and C8H18 respectively.
3. The structural formula: This shows us how the atoms are joined together
in the molecule. Structural formula are used to distinguish between
structural isomers. The structural formula of ethanoic acid is CH3COOH
and that of iso-octane is (CH3)3CCH2CH(CH3)2.
4. The displayed formula: This is similar to the structural
formula but it shows the atoms that are bonded together
and the type of bond involved (i.e. single, double, triple
or dative).
5. Stereochemical formula: In as much as
the displayed formula tells us much
about a molecule, it indicates nothing
about the shape of the molecule. Since
it is difficult to represent the shape of a
three-dimensional molecule on a two-
dimensional page, we use the principles
of stereochemical formula.
Stereochemical formula represents the
three-dimensional shape of a molecule.
6. Skeletal formula: This reduces the
molecular structure down to its bare
minimum, omitting all carbon atoms and
all the hydrogen atoms joined to carbon
atoms, and therefore show only the
carbon-carbon bonds. It can also be
referred to as the line-angle formula. It is
an excellent way of describing larger and
more complicated molecules. The true
skeletal formula shows only the carbon-
carbon bonds.
Representation of Carbon Rings in
Formula for Cyclic Hydrocarbons
TASK
HYBRIDIZATION
• 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.
• This intermixing usually results in the formation of hybrid
orbitals having entirely different energies and shapes
from the original hybrid orbitals.
• Hybridization of one 2s orbital and three 2p orbitals for
carbon forms four hybrid orbitals.
• These hybrid orbitals are called sp3 hybrid orbitals because
they are formed from one s orbital and three p orbitals.

• These new hybrid orbitals are intermediate in energy

between the 2s and 2p orbitals.
• Mixing a spherical 2s orbital and three dumbbell shaped 2p orbitals
together produces four orbitals having one large lobe and one small
lobe, oriented toward the corners of a tetrahedron. Each large lobe
concentrates electron density in the bonding direction between two
nuclei. This makes bonds formed from hybrid orbitals stronger than
bonds formed from pure p orbitals.
• Covalent bonds in polyatomic molecules are formed by
the overlap of hybrid orbitals or of hybrid orbitals with
unhybridized ones.
Sigma and Pi Bonding
• When orbitals approach each other in a head-to-head
fashion, the resulting covalent bonds are called sigma (σ)
bonds. Head-to-head overlap is the most efficient way to
bond and results in relatively strong and stable bonds.
• When unhybridized two p orbitals approach each other
sideways, the resulting covalent bond is called a pi (∏)
bond. The pi bond is relatively long and diffuse. Sideways
overlap is less efficient than head-to-head overlap and
results in formation of weaker bonds.
ALKANES AND sp3
HYBRIDIZATION OF CARBON
• Alkanes are hydrocarbons where all the carbon atoms are
sp3-hybridized, all bonds are single bonds, and all carbons
are tetrahedral. Methane is the simplest alkane.
• The sp3-hybridized orbitals are oriented at an angle of
109°28’ or 109.5o
ALKENES AND sp 2

HYBRIDIZATION OF
CARBON
• The combination of one s and two p-orbitals to form three hybrid
orbitals of equal energy is known as sp2 hybridization.
• The sp2 hybridized orbitals are oriented at an angle of 120°.
• The geometry of the sp2 hybrid orbitals is trigonal planar, with the
lobes of the orbitals pointing towards the corners of a triangle
 ALKYNES AND sp
HYBRIDIZATION OF
• InCARBON
sp hybridization, the 2s orbital is mixed with one of the 2p
orbitals (e.g. 2px ) to give two sp hybrid orbitals of equal energy.
This leaves two 2p orbitals unaffected (2py and 2pz ) with slightly
higher energy than the hybridized orbitals.
• The geometry of the sp hybrid orbitals is linear and they are
oriented at an angle of 180o.
NOTE:
• To determine the hybridization of an atom in
a molecule, we count the electron domains
for that atom. Electron domains include both
bonded and non-bonded electrons.
TASK