Worksheet 14 - Hybridization

The hybridized molecular orbitals have different shapes and energy levels than the
atomic orbitals. The number of molecular orbitals created by hybridization depends on
the number of atomic orbitals that are mixed to form them.

In forming sp3 hybridized orbitals, four atomic orbitals are mixed, one s and three p.
The energy diagram for this process is shown below. The hybridized orbitals are higher
in energy than the s orbital, but lower in energy than the p orbitals.

p
energy
sp3
s hybridization

atomic orbitals hybridized orbitals

Carbon has 4 valence electrons. Add these electrons to the atomic and molecular
orbitals. This hybridization gives tetrahedral geometry.

With this hybridization, C will form four equivalent σ bonds.

Draw a similar energy diagram for sp3 hybridized oxygen.

p
energy
sp3
s hybridization

How many σ bonds will be formed? 2

How are the other sp3 orbitals used? The other sp3 orbitals hold the
oxygen lone pairs
Do the same for sp3 hybridized nitrogen.

p
energy
sp3
s hybridization
In some Lewis structures, there are only three equivalent bonds formed. To create
three equivalent hybridized orbitals, mix three atomic orbitals.

Draw and name the orbitals formed in this hybridization, then add the electrons for
sulfur. Since the hybridized orbitals are close in energy, every orbital is filled with one
electron before electrons are paired.

p
p
energy sp2

s hybridization

The hybridized orbitals will form __1___ σ bond(s).

The unhybridized orbital will form __1___ π bond(s).

There will be __2___ lone pair(s).

This hybridization gives trigonal planar geometry.

In linear molecules, like CO2, the central atom has only two equivalent bonding orbitals.
Draw the energy levels and name the orbitals formed in this hybridization.

p
p
energy sp

s hybridization

Fill in the electrons for carbon and determine the number and type of bonds formed.
There will be 2 sigma bonds (with sp) and 2 pi bonds (with p)
In CO2, determine the hybridization of the oxygen atoms. Complete the energy
diagram for the oxygens. Draw the structure of CO2.

p
p
energy sp2
: :

: :

s hybridization O C O
Each oxygen atom forms 1 sigma bond (with the sp2) and 1 pi bond
(with the p) with the sp and p orbitals on the carbon atom
In atoms with n=3 or larger, the d orbitals can also be hybridized. In molecules with five
molecular orbitals, five atomic orbitals are mixed:

_d_ + _s_ + _p_ + _p_ + _p_

This will give trigonal bipyramidal geometry and is called dsp3 hybridization.

Finally, molecules with octahedral geometry, will have __6 __ molecular orbitals. This
2 3
hybridization is called __d sp ______ .

Shown below is a portion of the chart from Worksheet 13. Fill in the hybridization for
each of the compounds.

compound bonds lone geometry shape hybridization

pairs

bonds + lone pairs = 6

SF6 6 0 octahedral octahedral d2sp3
bonds + lone pairs = 4
NH3 3 1 tetrahedral trigonal sp3
pyramidal
bonds + lone pairs = 6
ICl4 -
4 2 octahedral square d2sp3
planar
bonds + lone pairs = 4
CF4 4 0 tetrahedral tetrahedral sp3
bonds + lone pairs = 3
SO3 3 0 trigonal trigonal sp2
planar planar
bonds + lone pairs = 5
SF4 4 1 trigonal seesaw dsp3
bipyramidal
bonds + lone pairs = 2
CO2 2 0 linear linear sp
bonds + lone pairs = 4
H2O 2 2 tetrahedral V-shaped sp3
bonds + lone pairs = 3
NO2 -
2 1 trigonal V-shaped sp2
planar
Fill in the chart below and then complete the Lewis structures for the molecules shown
below and fill in those charts.

element Lewis symbol # bonds # lone pairs

C 4 0
C
N 3 1
N
H 1 0
H
O 2 2
O
Halogen 1 3
F

1 σ bonds __7__
H O atom # bond angle hybridization
H C C O H 1 120 sp2
π bonds __ 1__
3 2 2 109 sp3
H 3 120 sp2
acetic acid

H H
1 atom # bond angle hybridization
C C C N σ bonds _6___
2 1 180 sp
H 3 2 180 sp
π bonds _3___
acrylonitrile 3 120 sp2

H
2
HO H C H σ bonds 25__ atom # bond angle hybridization
H C N C C N 1 120 sp2
π bonds 4__ 2 120 sp2
H C C H
C 3 109 sp3
O N N 1
H C H
3
H
caffeine
 The molecule shown to the left is riboflavin
H (vitamin B2). Answer the following questions
H O C H about its structure.
a) how many carbons are sp3 hybridized? 8
H C O H
H O C H sp2 hybridized? 10
H C O H
sp hybridized? 0
H C H
H H H C H b) How many nitrogens are sp3 hybridized? 2
H C C N N
C C C C O sp2 hybridized? 2
H
H C C C N
C C N C H sp hybridized? 0
H
H H O
c) How many oxygens are sp3 hybridized? 4

sp2 hybridized? 2

sp hybridized? 0

d) How many σ bonds are there in total? 52

e) How many π bonds are there in total? 7

f) Which of the three rings are planar?

The ring on the left, in which all carbon
atoms are sp2 hybridized

The acetate ion, C2H3O2- , has both oxygens bonded to the same carbon.

a) Draw the Lewis structure and all resonance forms.

H sp2 H sp3

O C C H O C C H

H sp3 H
O O
sp2
b) Label the hybridization around each carbon.

c) Pick one resonance structure and label the hybridization of each oxygen.

d) How many σ and π bonds are present? 6 sigma bonds, 1 pi bond

e) Which atom carries the formal negative charge? the oxygen with 3 lone pairs