Molecular Geometry and

Hybridization of Atomic Orbitals

1
VSPER (Valence shell electron pair repulsion)

The VSEPR theory assumes that each atom in a molecule will achieve a
geometry that minimizes the repulsion between electrons in the
valence shell of that atom. The five compounds shown in the figure
below can be used to demonstrate how the VSEPR theory can be
applied to simple molecules.
VSEPR model:

Predict the geometry of the molecule from the electrostatic

repulsions between the electron (bonding and nonbonding) pairs.

# of atoms # lone
bonded to pairs on Arrangement of Molecular
Class central atom central atom electron pairs Geometry

AB2 2 0 linear linear

B B

3
 0 lone pairs on central atom

Cl Be Cl

2 atoms bonded to central atom 4

5
6
7
 VSEPR
# of atoms # lone
bonded to pairs on Arrangement of Molecular
Class central atom central atom electron pairs Geometry

AB2 2 0 linear linear

trigonal trigonal
AB3 3 0
planar planar
AB4 4 0 tetrahedral tetrahedral
trigonal trigonal
AB5 5 0
bipyramidal bipyramidal
AB6 6 0 octahedral octahedral

8
9
10
Introduction to Organic Chemistry
 The Phlogiston Theory
The Phlogiston (Gr., to set on fire) Theory was
prevalent in the 18th century. When metals were
heated in air, a calx was formed (an oxide today) and
phlogiston was lost. Since the calx was always
heavier than the metal, phlogiston must have a
negative mass. Carbon (charcoal) was rich in
phlogiston because when it was heated with a calx
(phlogiston poor), the metal (rich in phlogiston) along
with “fixed air (CO2)”was formed.

Georg Ernest Stahl

(1660-1734)
 The Co-Discoverer of Oxygen

Priestley heated red mercuric oxide in a sealed system to

produce liquid, metallic mercury and dephlogisticated air
(oxygen). The mass of the vessel did not change. He also
noted that dephlogisticated air was essential for breathing. In
spite of these observations, he nonetheless remained a
supporter of the Phlogiston Theory.

HgO + heat = Hg + O

Joseph Priestley
(1733-1804)
 Lavoisier and Combustion

Lavoisier was able to demonstrate that mass is conserved in

chemical reactions. The calx has a higher mass than the metal
from which it is derived. It is oxygen that is gained, not
phlogiston that is lost.

Antoine-Laurent Lavoisier, a meticulous experimenter,

revolutionized chemistry. He established the law of
conservation of mass, determined that combustion and
respiration are caused by chemical reactions with what he
named “oxygen,” and helped systematize chemical
nomenclature, among many other accomplishments.
Antoine-Laurent Lavoisier (1743-1794) and His Wife
(Marie-Anne-Pierrette
Paulze, 1758-1836)
 Atomic Theory

Dalton proposes the atomic theory in the eary

19th century. Uses circles for the various
elements.

1. Elements composed of indivisible atoms

2. Elements have defined and different masses

3. Elements combine in simple numerical

ratios - Law of Multiple Proportions

Hydrogen = 1
Azot = 4.2
John Dalton
Carbone = 4.3
(1766-1844) Oxygen = 5.5
 Electrochemical Theory

Berzelius provided the modern symbols of the elements and

defined isomerism (equal parts). Isomers have the same
composition but not the same physical properties. Dualism
held that organic compounds, like inorganic ones, had
electropositive and electronegative componnets.

Discovers: Ce, Se, Th, Si, Zr, etc.

Electrochemical Theory (Dualism)

The theory held that all molecules are salts composed of basic and acidic
oxides.

Jons Jacob Berzelius

(1779-1848)
Vitalism

A theory that an organic molecule cannot be

produced from inorganic molecules, but
instead can only be produced from a living
organism or some part of a living organism.
 The Beginning of the End for Vitalism

Vitalism held that organic compounds (derived from living or

deceased organisms) were different from inorganic compounds.
The formation of urea (organic) from ammonium cyanate
(inorganic) countered this argument. Berzelius, Wohler’s mentor,
expressed support of the experiment as an example of isomers

1828 - Converts ammonium cyanate

Friedrich Wöhler CH4N2O (inorganic)
(1800 - 1882) into urea
CH4N2O (organic)
An example of isomers
Begins the downfall of Vitalism
Wöhler mixed silver cyanate and ammonium chloride to produce solid silver chloride and aqueous
ammonium cyanate:

He then separated the mixture by filtration and tried to purify the aqueous ammonium cyanate by
evaporating the water.
 Valence

Frankland pointed out that every element tends to combine

with a certain number of atoms of other elements, and this
number, called the valence, is a constant for a given element.

1852 - recognizes the ability of N, P, As, and Sb to combine

with 3 and 5 other elements.

Edward Frankland
(1825 - 1899)
 1857 - Developed the idea of
valence with carbon compounds.
1858 - Quadravalence of carbon
1865 - Structure of benzene
1861 - Lehrbuch der
Organischen Chemie

Friedrich August Kekule

(1829-1896)

Acetic Acid
 Kekule's 19 formulas
for acetic acid (C2H4O2) from his
Lehrbuch der
Organischen Chemie in 1867
 1858

Acetic Acid

Couper proposed an early theory of chemical structure and

bonding. He uses lines to connect atoms.

(1831-1892)
 1901 - 1st Nobel Prize in Chemistry

Jacobus Henricus
van’t Hoff
(1852 - 1911) Carbon is tetrahedral
 1869 - Mendeleev’s Periodic Table

1897 - Thomson Discovers the Electron

1902 - Lewis’s Cubic Model of the Atom

(Covalence)

Gilbert N. Lewis 1916 - Lewis Dot Formula

(1875-1946)
 Quantum Mechanics leads to ...

Resonance
Hybridization
Molecular Orbital Theory

The Nature of the Chemical Bond (1939)

Linus Pauling
(1901 - 1994)
 Organic Chemistry

• Organic chemistry is the chemistry of carbon compounds.

What makes Carbon so unique and special
element?
 The position of carbon in the periodic table

Figure 1
 The chemical diversity of organic compounds

4 carbons linked with single bonds, 1 oxygen and needed hydrogens.

Figure 2
• Carbon
• Has 4 valence electrons
• Makes 4 covalent bonds to fill its octet
• Can include double and triple bonds

• Hydrocarbon
• Compound with only carbon and hydrogen
 Electronic Configurations of Atoms

• Valence electrons are electrons on the outermost shell of the atom.

 Bonding Patterns
Valence # Bonds # Lone Pair
electrons Electrons
C 4 4 0

N
5 3 1

O
6 2 2

Halides
7 1 3
(F, Cl, Br, I)
Lone Pairs
 Resonance Forms
• In a resonance form, only the electrons are moved. Connectivity between atoms
stay the same.
• The real structure is a hybrid of the different resonance forms.
• Arrows connecting resonance forms are double headed.
• Spreading the charges over two or more atoms stabilize the ion.
 Resonance Forms

• The structure of some compounds are not adequately represented by a single Lewis structure.
• Resonance forms are Lewis structures that can be interconverted by moving electrons only.
• The true structure will be a hybrid between the contributing resonance forms.
 Isomerism
• Molecules that have the same molecular formula, but differ in the
arrangement of their atoms, are called isomers.
• Constitutional (or structural) isomers differ in their bonding
sequence.
• Stereoisomers differ only in the arrangement of the atoms in space.
 Constitutional Isomers

• Constitutional isomers have the same chemical formula, but the atoms are
connected in a different order.
• Constitutional isomers have different properties.
• The number of isomers increases rapidly as the number of carbon atoms
increases.
 Organic Chemistry in Everyday Life

• Smells & tastes: fruits, fish, mint

• Medications: aspirin, Tylenol, decongestants, sedatives, insulin
• Addictive substances: caffeine, nicotine, alcohol, narcotics
• Hormones/Neurotransmitters: adrenaline, dopamine, serotonin
• Food: carbohydrates, protein, fat, vitamins
• Genetics: DNA, RNA
• Consumer products: plastics, nylon, rayon, polyester
 SOURCES OF ORGANIC COMPOUNDS

There are three generally accepted sources of organic compounds:

o1. carbonized organic matter:

Carbonization is the term for the conversion of an organic substance
into carbon or a carbon-containingresidue through pyrolysis or
o destructive distillation.

Example: the generation of coal, gas and coal tar from coal to raw coal. Fossil
fuels from vegetable matter, producing coke, the charcoal making
process, etc.

2. Living organisms
o
The chemical compounds of living things are known as organic compounds because of their association with
organisms and because they are carbon-containing compounds.
o
Among the numerous types of organic compounds, four major categories are found in all living things:
carbohydrates, lipids, proteins, and nucleic acids
3. Invention/Human ingenuity
o
Antibiotics, aspirin, vanilla flavoring, and heart drugs are examples of substances that no longer
have to be obtained directly from nature, they are manufactured in laboratories from organic starting
materials.
o
Each year over 250,000 new chemical compounds are discovered and many of these are
products of scientists' imaginations, exploration.
o
Plastics are excellent examples of substances that are the product of invention - they are not
found anywhere in nature.
Properties of typical organic and inorganic compound
Property Organic compound Inorganic
compound
Bonding with Usually covalent Often ionic
molecule
Generally weak Quite strong
Forces between
(Intermolecular force) (Electrostatic force)
molecules
Gases, liquids or low- Usually high-
Normal physical melting-point solids melting-point solids
state
Flammability Often flammable Usually non-
flammable
Solubility in water Insoluble Soluble
Conductivity Non-conductor Conductor
Rate of chemical Slow and complex Fast and simple
reaction