Hybridization 1 SPRING 2023

CHEM 222 SPRING SEMESTER 2023
HYBRIDIZATION I – HYBRIDIZATION IN THE ALKANES: CARBON ATOMS FORMING SIGMA (σ) BONDS
OBJECTIVE: Students would be introduced to Hybridization Theory and thus understanding how a carbon
atoms is able to form four single bonds.
Atomic orbitals can combine and overlap to give new orbitals:

 when orbitals on the same atom interact, they form hybrid atomic orbitals
(HAOs) that define the geometry of the bonds (i.e. tetrahedral, trigonal planar,
etc.). The type of hybrid orbitals formed depends on the number of atomic
orbitals which undergo hybridization.
 when orbitals on different atoms interact, they produce molecular orbitals
(MOs) that lead to bonding interactions (i.e. bonds are formed). Molecular
orbitals may be sigma (σ) or pi (π).
HYBRIDIZATION (explanation of how a carbon atom is able to form four bonds).

{Wade: Section 2-4}
Only unpaired electrons in the valence shell of the atom can take part in bonding. The
carbon atom has an electron orbital configuration of 1s2, 2s2, 2px1, 2py1. So if the carbon atom
only has two unpaired electrons, how does it form four bonds in its compounds? To
explain how this is possible Linus Pauling developed the concept of HYBRIDIZATION.
 Pauling argued that the electron configuration of a carbon atom bonded to other atoms
need not be the same as the configuration of a free carbon atom. He argued that by
mixing (“hybridizing”) some (or all) of the electron orbitals in the second electron
shell, hybrid orbitals would be formed.
 The rule we follow in determining the DEGREE of HYBRIDATION a carbon atom
undergoes is:
** The degree of hybridization is determined by the number of atoms to which the
carbon atom is DIRECTLY attached (bonded to) ** {know this rule & how to apply
it}
{This handout looks at the bonding in the alkanes (general formula: CnH2n+2), alkyl
compounds, and the cycloalkanes (CnH2n). In these compounds, each carbon is
bonded to four other atoms so four hybrid orbitals need to be formed}
(Subsequent handouts would look at the hybridization in alkenes and alkynes.)
 The simplest hydrocarbon is methane, CH4. You have already met methane in
molecular geometry: four (4) covalent bonds directed to the corners of a
tetrahedron, each H-C-H bond angle 109.50.
 The four second shell electrons (the two 2s and the two 2p electrons) will be
distributed singly among the hybrid orbitals to allow bond formation with four
other atoms.
Let’s see how this applies to the bonding in methane (and in general, the alkanes).
In methane, the carbon atom has to form four bonds; so by applying the “degree of
hybridization” rule four (4) hybrid orbitals need to be formed.
First, one of the 2s electrons is promoted to the empty 2pz orbital. With no hybridization
the four covalent bonds which could be formed
would not all be identical (a bond formed
by an s orbital would be of lower energy
than one formed by a p orbital).
However, the four C –H bonds in

methane are identical! Four
identical bonding orbitals are
formed by mixing (hybridizing) the
2s orbital and all three 2p orbitals
(2px, 2py, and 2pz) to form four (4)
hybrid sp3 orbitals.
 These sp3 hybrid orbitals have
25% s orbital character and 75%
p orbital character {see left}. All
four sp3 orbitals are “degenerate”
(equal energy), and according to
Hund’s Rule the four electrons
will singly occupy the four orbitals making them all
available for bonding. The axes of the sp3 orbitals point to
the corners of a tetrahedron, hence the bond angles of
109.50. Each carbon-hydrogen (C-H) bond of methane is a
sigma (σ) bond with a half-filled 1s orbital on a hydrogen (H)
atom overlapping with a half-filled sp3 orbital on the carbon
(C) atom. {see left}
**(sp hybridization – the s orbital + the three p orbitals)**
3
Bonding in ethane (quick look): Two sp3 hybrid carbon atoms bond with each other & six
hydrogen atoms.
 The hybridization of the carbon atoms in the CYCLOALKANES is also sp3. This is
because in a cycloalkane, each carbon atom is bonded to four other atoms, so four
hybrid orbitals are needed. The general formula of the cycloalkanes, CnH2n, is due to
two hydrogen atoms being lost from two adjacent carbon atoms in the process of the
cyclo-ring formation (see below).
Note that any atom with sp3 hybridization would have some variation of tetrahedral
geometry!!
Richard Jacques/ Jan 2023

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CHEM 222 SPRING SEMESTER 2023

Atomic orbitals can combine and overlap to give new orbitals:

HYBRIDIZATION (explanation of how a carbon atom is able to form four bonds).

However, the four C –H bonds in

Richard Jacques/ Jan 2023

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