Organic Chemistry: Orbitals Hybridization

Organic Chemistry
Orbitals Hybridization
Dr. Talal Ahmed Awad

Department of Chemistry
1
sp3 Hybrid Orbitals
• Carbon has four valence electrons (2s2 2p2) and forms four
bonds.
• Because carbon uses two kinds of orbitals for bonding, 2s
and 2p, we might expect methane to have two kinds of C-H.
bonds.
• In fact, all four C-H bonds in methane are identical and are
oriented toward the corners of a regular tetrahedron
• How can we explain this?

• s orbital and three p orbitals on an atom can combine, or
hybridize, to form four equivalent atomic orbitals with
tetrahedral orientation.
• These tetrahedrally oriented orbitals are called sp3
hybrid orbitals.
• Note that the superscript 3 in the name sp3 tells how
many of each type of atomic orbital combine to form the
hybrid (1 s orbital + 3 p orbitals).
• hybridization explains how carbon forms four equivalent
tetrahedral bonds.
• sp3 hybrid orbitals form stronger bonds than do
unhybridized s or p orbitals.
Four sp3 hybrid orbitals, oriented to the corners of a regular tetrahedron,
are formed by the combination of an s orbital and three p orbitals (red/blue).
The sp3 hybrids have two lobes and are unsymmetrical about the nucleus,
giving them a directionality and allowing them to form strong bonds when
they overlap an orbital from another atom.
Structure of Methane
• When each of the four identical sp3 hybrid orbitals of a
carbon atom overlaps with the 1s orbital of a hydrogen
atom, four identical C-H bonds are formed and methane
results.
• Each C-H bond in methane has a length of 109 pm.
• The angle formed by each H-C-H is 109.5°, the so-called
tetrahedral angle.
The structure of methane, showing its 109.5° bond angles.
sp3 Hybrid Orbitals and the
Structure of Ethane
• The same kind of orbital hybridization that accounts for
the methane structure also accounts for Ethane, C2H6.
sp2 Hybrid Orbitals and the
Structure of Ethylene
• Ethylene, has the structure H2C=CH2 and contains a
carbon–carbon double bond.
• The 2s orbital combines with only two of the three
available 2p orbitals.
• Three sp2 hybrid orbitals result, and one 2p orbital
remains unchanged.
• The three sp2 orbitals lie in a plane
at angles of 120° to one another,
with the remaining p orbital
perpendicular to the sp2 plane.
• When two carbons with sp2 hybridization approach each
other, they form a strong σ bond by sp2–sp2 head-on overlap.
• At the same time, the unhybridized p orbitals interact by
sideways overlap to form what is called a pi (π) bond.
• The combination of an sp2–sp2 σ bond and a 2p–2p π bond
results in the sharing of four electrons and the formation of a
carbon–carbon double bond.
• Note that the electrons in the σ bond occupy the region
centered between nuclei, while the electrons in the π bond
occupy regions above and below a line drawn between
nuclei.
• To complete the structure of ethylene, four hydrogen atoms
form σ bonds with the remaining four sp2 orbitals.
The structure of ethylene.
One part of the double bond in ethylene results from s (head-
on) overlap of sp2 orbitals, and the other part results from π
(sideways) overlap of unhybridized p orbitals (red/blue).
The π bond has regions of electron density above and below a
line drawn between nuclei.
• Ethylene thus has a planar structure, with H-C-H and H-C-C
bond angles of approximately 120°. .
sp Hybrid Orbitals and the Structure
of Acetylene
• carbon also can form a triple bond by sharing six electrons.
• For the triple bond in a molecule such as acetylene, H-C≡C-H,
we need a third kind of hybrid orbital, an sp hybrid.
• A carbon 2s orbital hybridizes with only a single p orbital.
• Two sp hybrid orbitals result, and two p orbitals remain
unchanged.
• The two sp orbitals are oriented 180° apart on the x-axis,
while the p orbitals are perpendicular on the y-axis and the z-
axis.
• When two sp-hybridized carbon atoms approach each
other, sp hybrid orbitals on each carbon overlap head-on
to form a strong sp–sp σ bond.
• At the same time, the pz orbitals from each carbon form a
pz–pz π bond by sideways overlap, and the py orbitals
overlap similarly to form a py–py π bond.
• The net effect is the sharing of six electrons and
formation of a carbon–carbon triple bond.
• The two remaining sp hybrid orbitals each form a σ bond
with hydrogen to complete the acetylene molecule.
• As suggested by sp hybridization, acetylene is a linear
molecule with H-C-C bond angles of 180°.
• The C-H bonds have a length of 106 pm and.

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Organic Chemistry

Dr. Talal Ahmed Awad

• How can we explain this?

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