Organic Chemistry PWPT

Organic Chemistry
CHM 121
BY
DR OLOYE-AKOREDE
Introduction to Organic Chemistry
• Organic chemistry is the area of chemistry that involves the study of carbon and its
compounds.
• Carbon is known to form a seemingly unlimited number of compounds.
• The uses of organic compounds impact our lives daily in medicine, agriculture, and general
life.
• Organic chemicals were used in ancient times by Romans and Egyptians as dyes, medicines
and poisons from natural sources, but the chemical composition of the substances was
unknown.
• Organic compounds were isolated from nature in the pure state and analytical methods were
• Organic chemistry developed into a productive and exciting science in the
nineteenth century.
• Many new synthetic methods, reaction mechanisms, analytical techniques and

structural theories have been developed.
• Toward the end of the century much of the knowledge of organic chemistry
has been expanded to the study of biological systems such as proteins and
DNA.
• The vast information available today means that students of organic chemistry
must learn about organic reactions, mechanism, synthesis, analysis, and
biological function.
Orbital Hybridization: Is the phenomenon of mixing atomic orbitals of similar energies
to form an equivalent number of entirely new orbitals of identical shape and energy, called
"hybrid orbitals“.
Types of Hybridization
There are several types of hybridization, including:
• sp,
• sp2,
• sp3,
• dsp3, and
• d2sp3, each of which describes the atomic orbitals being mixed.
• The orbitals which undergo hybridization should not be energetically much different.
The number of hybrid orbitals generated is always equal to the number of atomic orbitals
combined.
SP3 –Hybridisation
In this process, one 2s and three 2p orbitals on hybridization, yield a set of four new
equivalent orbitals.
These new orbitals are called hybrid orbitals.
Since they are formed by combining one s and three p orbitals, they are called sp3
hybrid orbitals.
All the four SP3 hybrid orbitals are of equal energy and each one of them has 25% s
character and 75% p character.
Fig 1: a) Hybridisation of one 2s and three 2p orbitals to yield four sp3 hybrid orbitals. b) Four sp3
hybrid orbitals directed towards the corners of a tetrahedron: small back lobes are not shown. c)
Formation of methane molecule.
• The spatial orientation of these orbitals is obtained by mathematical calculations in
Fig. 1 (b). This is in accordance with the VSEPR theory.
• From the figure that these orbitals are directed towards the corners of a tetrahedron
and the bond angle between any two sp3 hybrid orbitals is 109.5 o.
• In methane molecule, each of the four sp3 hybrid orbitals overlaps with 1s orbital of
four hydrogens in Fig. 1 (c).
• Note that the bonds so formed, i.e: the C – H bonds, are ∂ (sigma) bonds.
• If instead of combining with hydrogens, the hybrid orbital forms a bond with the
similar hybrid orbital of another carbon atom, then a C – C bond will result instead of
the C – H bond.
• The C-C has a bond length of 154 picometer (pm) and a bond energy of 348 kJ mol -1.
Sp2-Hybridisation
• In this type of hybridization, the 2s orbital of the carbon is hybridized with only
two of the three available 2p orbitals.
• Since three orbitals are hybridized, three equivalent SP 2 hybrid orbitals are
obtained.
• According to the VSEPR theory, these orbitals are oriented in space making an
angle of 120o with each other as shown in Fig. 2(a).
• Note that the three SP2 hybrid orbitals are in one plane. The third p orbital which
is not utilized for hybridization is perpendicular to the SP 2 hybrid orbitals.
• When two such SP2 hybridized carbon atoms form a bond, the C – C bond
formed is again a δ bond.
• If the rest of the sp2 hybrid orbitals on each carbon atom overlap with 1 s
orbital of the two hydrogen atoms, then as shown in Fig. 2 (b) the two
unhybridized p orbitals on the two carbon atoms are parallel to each other.
• These p orbitals can overlap sideways to yield a second bond, known as π

(pi) bond which is shown in Fig. 2(c).
• The C = C bond length for ethylene molecule so obtained is 134 pm. This
value can be compare with C – C single bond length as in the case of
ethane.
Fig. 2: (a) SP2 hybrid orbitals. (b) Formation of C – C δ bond. (c) Formation of a π bond in ethylene
molecule.
SP-Hybridization
• The third type of hybridization involving s and p orbitals in cases
where a triple bond is stipulated.
• In carbon atom when 2s and only one of the three 2 p orbitals
hybridize, the hybridization is known as SP - hybridization.
• This leads to two new equivalent SP hybrid orbitals.
Fig. 3: (a) Two SP hybrid orbitals. (b) Formation of one δ (sigma) bond. (c) Formation of two π bonds.
• When one of the two SP hybrid orbitals on each carbon atom combines with
another, a C – C sigma bond is formed.
• The second SP hybrid orbital on each carbon forms a sigma bond with 1s orbitals
of two hydrogens, as shown in Fig. 3 (b).
• This leaves two p orbitals on each carbon atom which are not used in SP
hybridization.
• These p orbitals are perpendicular to each other and also to the sigma bond.
• These p orbitals can overlap laterally to give rise to two π bonds. Such a bond is
called a triple bond and we get the acetylene molecule, as shown in Fig.3 (c)
• The C = C bond in acetylene has a bond length of 120 pm and the H – C – C-H
angle is 180o which shows that it is linear.

Organic Chemistry PWPT

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Organic Chemistry

• Carbon is known to form a seemingly unlimited number of compounds.

• Many new synthetic methods, reaction mechanisms, analytical techniques and

These new orbitals are called hybrid orbitals.

• These p orbitals can overlap sideways to yield a second bond, known as π

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