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VSEPR Theory
Getting in Shape
2
Chapter 10 Notes
Molecular Shapes
• The approximate shape of a molecule can be
predicted from the Lewis dot structure using the
Valence-Shell Electron-Pair Repulsion (VSEPR)
model, which depicts electrons in bonds and lone
pairs as “electron groups” or “charge clouds” that
repel one another and stay as far apart as possible.
– Every group of electrons, whether in a bond or a
lone pair, counts as a charge cloud. (Multiple
bonds count as one charge cloud.
– There are five basic shapes in the VSEPR model,
with some variations depending on how many
charge clouds are in lone pairs vs. covalent bonds.
• The three-dimensional shape of a molecule is often
important in determining its chemical behavior,
particular for biologically important molecules. 3
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MOV: VSEPRmovie
Chapter 10 Notes
O C O
H C H
F
O S O
F B F
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Chapter 10 Notes
H C H
H O H
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Chapter 10 Notes
Cl
Cl P Cl
Cl Cl
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Chapter 10 Notes
F S F
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F Br F
F Xe F
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Chapter 10 Notes
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F Br F
F F
F Xe F
F
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Chapter 10 Notes
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Chapter 10 Notes
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Chapter 10 Notes
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Chapter 10 Notes
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Chapter 10 Notes
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Chapter 10 Notes
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Chapter 10 Notes
b. NH3
c. SF2
d. CF4
e. NO3-
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g. HCN
h. SbF5
i. XeF2
j. XeF4
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Chapter 10 Notes
Valence Bond
Theory
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Models of Bonding
• VSEPR theory accounts for the shapes of molecules,
but does not tell us how those shapes come about.
• More advanced models of chemical bonding extend
the concepts of quantum mechanics and wave
functions/orbitals to describe molecules, and allow
very precise calculations to be made about the
properties of molecules.
– Valence Bond (VB) theory is a relatively simple
model which pictures covalent bonds as arising
from the overlap of orbitals on adjacent atoms.
– Molecular Orbital (MO) theory is a more
sophisticated model which pictures covalent
bonds forming from molecular orbitals
delocalized over the entire molecule.
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Chapter 10 Notes
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Figure 10.6
Chapter 10 Notes
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Chapter 10 Notes
Hybrid Orbitals
• The shapes of s, p, and d orbitals do not account for
the shapes of molecules, so we must use different
orbitals in a molecule from those in isolated atoms.
– [For instance, carbon’s electron configuration has
2 half-filled p orbitals 90° from each other, yet
carbon forms four bonds to hydrogen atoms to
form CH4, with bond angles of 109.5 °.]
• The wave functions for the atomic orbitals derived
from the Schrödinger equation are mathematically
combined to form new wave functions called hybrid
atomic orbitals.
• The number of hybrid orbitals equals the number of
atomic orbitals which combine; we need one hybrid
orbital for each electron pair (bond or lone pair).
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Hybrid Orbitals
2 charge → 2 sp orbitals → linear (180°)
clouds
3 charge → trigonal planar
clouds 3 sp2 orbitals → (120°)
4 charge → 4 sp3 orbitals → tetrahedral (109.5°)
clouds
5 charge → 5 sp3d orbitals → trigonal bipyramidal
clouds (90°, 120°)
6 charge → 6 sp3d2 orbitals → octahedral (90°)
clouds
sp3 Hybridization
• When the s and all three p orbitals combine, the
resulting hybrid orbitals are sp3 hybrid orbitals.
sp3 Hybridization
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Figure 10.7 MOV: Hybridization
Chapter 10 Notes
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Chapter 10 Notes
H H H
C C
H
H H
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sp2 Hybridization
• When the s and two of the three p orbitals combine,
the resulting hybrid orbitals are sp2 hybrid orbitals.
sp2 Hybridization
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Figure 10.8
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Chapter 10 Notes
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Figure 10.9
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p p
σ-bond
sp2 sp2
sp2 sp2
sp2 sp2
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Chapter 10 Notes
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sp Hybridization
• When the s and one of the three p orbitals combine,
the resulting hybrid orbitals are sp hybrid orbitals.
sp Hybridization
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Figure 10.10
sp Orbitals in BeCl2
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Chapter 10 Notes
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Chapter 10 Notes
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Molecular Orbital
Theory
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Chapter 10 Notes
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Chapter 10 Notes
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Chapter 10 Notes
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Chapter 10 Notes
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Chapter 10 Notes
Interesting Shapes,
Beautiful Molecules,
Odor, and Handedness
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Interesting Molecules
O CH3 O
CH3 N
N
O O
OH
O N N
O
CH3
HN O
Caffeine O
OH H
O HO O
O O O
Taxol
O
H3C
CH3
H
CH3
α-Irone
O O
O
O
O
O
O
O O
O
O O
O
O
O
H H O
H O
HO O
O
Cholesterol
Olestra 68
Chapter 10 Notes
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Molecular “Handedness”
• A number of everyday things have a “handedness”
associated with them: hands (duh!), gloves, the
threads on screws or lightbulbs, etc.
– A right hand fits only into a right-handed glove.
– When these objects are reflected in a mirror, the
shape is inverted — i.e., a right-hand glove
reflected in a mirror looks like a left-hand glove.
• Some molecules also have a handedness which
causes them to adopt one of two or more possible
mirror image forms.
• This is most common with atoms of single-bonded,
sp3-hybridized carbon; a tetrahedral carbon with four
different things connected to it can be oriented in
one of two possible ways, and is said to be chiral.
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Chapter 10 Notes
C W W C
Z Z
Y mirror
Y
W W
X C Y Y C X
Z mirror Z 73
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Chapter 10 Notes
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Carvone
• Left-handed carvone is found in mint plants, and has
a characteristic odor or spearmint.
• Right-handed carvone occurs in several herbs, and
has the odor of caraway seeds.
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Chapter 10 Notes
Thalidomide
• Until 1956, thalidomide was considered to be a very
safe, popular sedative; the largest market was for
pregnant women experiencing morning sickness.
However, it was found to cause massive birth
defects in women who used it in the early states of
pregnancy, and was banned in Europe; it was never
authorized for sale in the U.S. (The thalidomide tragedy was
a major rationale behind the passage of the Drug Amendments Act in
1962, which greatly expanded the amount of preclinical testing that was
required for new drugs.)
O
O
O N O
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H
Cholesterol
• Cholesterol has 8 chiral carbons, and can exist in a
maximum of 28 = 256 different forms; there is only
one naturally-occurring form of cholesterol.
HO
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