INTRODUCTION TO ORGANIC CHEMISTRY

Chemical
History Atomic Structure Lewis Structure
Bonding

Resonance Molecular
Formal Charges Hybridization
Structure Orbitals

Bond-Line Intermolecular An Introduction

Molecular Forces of to Functional
Representation Attraction Groups
ORGANIC
CHEMISTRY AND
ITS HISTORY
ORGANIC
CHEMISTRY
✓ Deals with the compounds of carbon
• Some compounds that contain the element
carbon are not organic compounds. Examples
include carbon dioxide (CO2), sodium
carbonate (Na2CO3), and sodium bicarbonate
(NaHCO3).

✓ Organic chemistry was singled out as a separate

discipline for historical reasons.

✓ Organic chemicals affect virtually every facet of our

lives, and for this reason, it is important and useful
to know something about them.
HISTORY
VITALISM THEORY (19TH CENTURY)
organic compounds were only those that came from living
organisms, and only living things could synthesize organic
compounds through the intervention of a vital force.

✓ Organic compounds: compounds in living things

✓ Inorganic compounds: compounds in nonliving things
HISTORY
Friedrich Wöhler (1828) discovered that an organic compound
called urea (a constituent of urine) could be made by evaporating
an aqueous solution of the inorganic compound ammonium
cyanate.
ORGANIC
COMPOUNDS’
COMMON FEATURES
✓ All organic compounds contain carbon atoms
and most contain hydrogen atoms.

✓ All carbon atoms have four bonds. A stable

carbon atom is said to be tetravalent.

✓ Other elements may also be present. Any

atom that is not carbon or hydrogen is called
a heteroatom. Common heteroatoms include
N, O, S, P, and halogens.

✓ Some compounds have chains of atoms and

some compounds have rings.
 Organic compounds are usually combustible.

Organic Organic compounds, in general, have lower melting and

boiling points.

Compounds Organic compounds are usually less soluble in water.

vs Several organic compounds may exist for a given formula.

Inorganic This is known as isomerism.

Compounds Reactions of organic compounds are usually molecular rather

than ionic. As a result, they are often quite slow.

The molecular weights of organic compounds may be very

high, often well over 1000.
SOURCES OF ORGANIC
COMPOUNDS
✓ N AT U R E :

fibers, vegetable oils, animal oils and fats, alkaloids, cellulose,

starch, sugars, and so on.

✓ SYNTHESIS:

A wide variety of compounds and materials are prepared by

manufacturing processes.

✓ F E R M E N T AT I O N :

Alcohols, acetone, glycerol, antibiotics, acids, and the like are

derived by the action of microorganisms upon the organic matter.
 Some Organic
Compounds
METHANE
simplest of all organic compounds, contains one
carbon atom.
-

main component of natural gas (occurs widely in

nature).
-

product of the anaerobic (without air)

decomposition of organic matter by bacteria.
 Some Organic
Compounds
ETHANOL
alcohol present in beer, wine, and other alcoholic
beverages. -

can be formed through fermentation or through

laboratory synthesis
Some Organic
Compounds

one most widely used antibiotics in the

AMOXICILLIN penicillin family.
 Some Organic
Compounds

FLUOXETINE
generic name for the antidepressant PROZAC

safe and highly effective in treating depression

Some Organic
Compounds

CAPSAICIN
one member of a group of compounds called vanilloids

responsible for the characteristic spiciness of hot peppers

active ingredient in pepper sprays used for personal defense and topical creams used for pain relief.
ATOMIC
STRUCTURE
 ATO M Building block of matter

19
20
 SCHRÖDINGER MODEL
assumes that the electron is a wave and tries to
describe the regions in space, or orbitals, where
electrons are most likely to be found.

21
22
23
 ATO M
BUILDING BLOCK OF MATTER

24
CHEMICAL
BONDING AND
LEWIS STRUCTURE
COVALENT BONDING
A covalent bond consists of the mutual sharing of one or
more pairs of electrons between two atoms.
 Bonding formation in atoms
One way to symbolize the bonding in a
covalent molecule is to use the KEKULÉ
STRUCTURES

each valence electron is symbolized

by a dot. A bonding pair of electrons
is symbolized by a pair of dots or by
a dash (—)
Bonding formation in atoms
 Identify the central and terminal
atoms. The central atom is bonded to
Determine the number of valence two or more atoms; terminal atoms
electrons (e) that must appear in the are bonded to one atom. H atoms are
Steps in writing structure. always terminal, C is always central,
central atoms are generally with
lowest electronegativity.
structures for
covalent With the remaining valence e,

compounds
compute first for the octet of the
Write the plausible skeletal structure
terminal atoms. If there are still
by joining the atoms using single
remaining e, complete the octet of the
covalent bonds first. Subtract 2 from
central atom. When all atoms have
the total valence e for each bond.
octets, then this is a satisfactory
Lewis structure
 Exceptions to the octet rule
1. Less than octet molecules, especially those in the 3A group ex. Be,
elements in group 3A like, BF3.

2. Odd-electron molecules (less than 8); examples, NO and NO2-. They

are sometimes called radicals for there is a tendency for the unpaired
electron to form covalent bond with an unpaired e of another
molecule.

3. Expanded octet have atoms of elements within and beyond the 3rd
period of periodic table that can form compounds where the central
atom can accommodate more than 8 electrons due to the availability
of their 3d orbitals. Examples include SF6 and PO43-
THREE DIMENSION REPRESENTATION
Let’s try to draw structures!
How many hydrogen atoms does phosphorus bond to in forming phosphine, PH3?
Let’s try to draw structures!
Draw both electron-dot and line-bond structures for chloromethane, CH3Cl.
Let’s try to draw structures!
Draw a molecule of chloroform, CHCl3, using solid, wedged, and dashed lines to show its tetrahedral
geometry.
 Charges of atoms

Atoms contain negatively charged electrons and positively

charged protons; the number of each determines the atom's
net charge.

FORMAL CHARGE OXIDATION NUMBER

 Formal Charge
the charge assigned to an atom in a molecule, assuming that
electrons in all chemical bonds are shared equally between atoms.
Formal Charge
 Formal Charge
Determines which lewis
structure is dominant!

Choose the lewis structure

in which the atoms bear
formal charges closest to
zero.
Choose the lewis structure
in which any negative
charge reside on the more
ELECTRONEGATIVE ATOM.
Let’s try to draw structures!
Perbromate (BrO4-1)
 Oxidation number
the number of charges an atom would have if the electrons were
completely transferred to the more electronegative of the bonded atoms in
a molecule (as if ionic bonding)
Isomers
different molecules having the
same molecular formula.

Constitutional isomers - have the

same molecular
formula, but the connectivity of
their atoms is different
Let’s try to draw structures!
C2H4Cl2 (two isomers)
Let’s try to draw structures!
C3H8O (three isomers)
RESONANCE
THEORY
The concept of
Resonance
Some molecules can’t be adequately
represented by a single Lewis structure

Resonance structures are two Lewis

structures having the same placement of
atoms but a different arrangement of
electrons
 The concept of
Resonance
The true structure is a composite of both
resonance forms and is called a resonance
hybrid.

The hybrid shows characteristics of both

resonance structures.
The concept of
Resonance
resonance allows certain electron pairs to
be delocalized over two or more atoms.

this delocalization of electron density adds

stability – resonance stabilized
INTERMOLECULAR
FORCES
Intermolecular Forces
✓ responsible for most of the physical
and chemical properties of matter
✓ attractive and repulsive forces that
arise between the molecules of a
substance
✓ forces mediate the interactions
between individual molecules of a
substance.
 Intermolecular Forces
ION-DIPOLE FORCE
an electrostatic interaction between a fully charged ion
and a neutral molecule that has a dipole

most commonly found in solutions, especially ionic

compounds dissolved in polar liquids
 Intermolecular Forces
DIPOLE-DIPOLE FORCE
electrostatic forces between two permanent polar molecules

positive end of one molecule is attracted to the negative end of

another molecule.
 Intermolecular Forces
HYDROGEN BONDING
a special type of dipole-dipole attraction between molecules, not a
covalent bond to a hydrogen atom

results from the attractive force between a hydrogen atom covalently

bonded to a very electronegative atom such as a N, O, or F atom
and another very electronegative atom
 Intermolecular Forces
ION-INDUCED DIPOLE
a weak attraction that results when the approach of an ion induces
a dipole in an atom or in a nonpolar molecule by disturbing the
arrangement of electrons in the nonpolar species
 Intermolecular Forces
DIPOLE-INDUCED DIPOLE
a weak attraction that results when a polar molecule induces a
dipole in an atom or in a nonpolar molecule by disturbing the
arrangement of electrons in the nonpolar species
 Intermolecular Forces
LONDON
DISPERSION FORCES
a temporary attractive force that results when the electrons in two
adjacent atoms occupy positions that make the atoms form
temporary dipoles
 Intermolecular Forces
LONDON DISPERSION FORCES
Intermolecular Forces
FUNCTIONAL
GROUPS
Functional
Groups
 Functional groups
an atom or a group of atoms with characteristic
chemical and physical properties. It is the
reactive part of the molecule

Determine a molecule’s geometry,

physical properties, and reactivity.
VALENCE BOND THEORY
AND MOLECULAR
ORBITAL THEORY
VALENCE BOND THEORY
describes covalent bond formation as well as the
electronic structure of molecules.

assumes that all bonds are localized bonds formed

between two atoms by the donation of an electron from
each atom
assumes that electrons occupy atomic orbitals of
individual atoms within a molecule, and that the electrons
of one atom are attracted to the nucleus of another atom.
VALENCE BOND THEORY
VALENCE BOND THEORY
 MOLECULAR ORBITAL THEORY
• each atom tends to combine together and form molecular orbitals.
 MOLECULAR ORBITAL THEORY
SECOND ENERGY LEVEL
MOLECULAR ORBITAL THEORY
O2 AND F2 B2, C2 and N2
 MOLECULAR ORBITAL THEORY
• BOND ORDER - number of bonds between a pair of atoms

𝐵𝑂𝑂2 = 2

𝐵𝑂𝑆𝑂2 = 1.5
 MOLECULAR ORBITAL THEORY
• DIAMAGNETIC: Atoms or molecules in which the electrons are paired, repelled by both poles of a magnetic

• PARAMAGNETIC: have one or more unpaired electrons; attracted to a magnetic field

The end