Basic Concepts of Organic

Chemistry
 Objectives
• After the completion of this lecture, the students will be
able to:
– Recognize the importance of organic compounds
– Compare properties of organic and inorganic
compounds
– Understand the structure of organic compounds and
its importance in terms of change in nature and
properties of the chemicals
– Describe the classification of organic compounds
– Differentiate the types of hydrocarbons; saturated and
unsaturated
 What is Organic Chemistry?

• The Chemistry of the Carbon-Carbon bond

– And of Carbon with other elements, especially
H, O, N, S, P and the halides (F, Cl, Br and I)
 Organic Chemistry is Unique
• Carbon forms stable, covalent bonds with itself

• Carbon forms stable multiple (double, triple)

bonds with itself and a variety of other elements

• Of the 10 most important challenges for the 21st

Century, 8 have organic chemistry involved
 Atomic Structure
• An atom is the smallest, indivisible unit of
matter for any given element
An atom consists of
– A small(10-14 – 10-15 m) dense, positively
charged NUCLEUS
AND
– Negatively charged electrons circulating the
nucleus (10-10 M)
 electron

Y-axis
Z-axis

X-axis

Nucleus 1 Proton + 0 Neutrons

The Atom - HELIUM
2 Protons, 2 Electrons
electron

electron
nn
Nucleus
2 Protons + 2 Neutrons
Atomic Number and Mass Number
• ATOMIC NUMBER (Z)
= the number of protons in the nucleus

• MASS NUMBER (A)

= the number of protons PLUS the
number of neutrons in the nucleus
• the mass of an electron is essentially
negligible
 Atomic and Mass Numbers
• HYDROGEN
Atomic NUMBER (Z) = 1 (1 proton)
MASS number (A) = 1 (1 proton + 0 neutrons)

• HELIUM
Atomic NUMBER (Z) = 2 (2 protons)
MASS number (A) = 4 (2 protons + 2 neutrons)
 Carbon
• CARBON
Atomic NUMBER (Z) = 6 (6 protons)

MASS number (A) = 12

(6 protons + 6 neutrons)
 ISOTOPES
Atoms that exist in more than one mass
number
ISOTOPES of Carbon
12C = 6 protons, 6 neutrons (stable; 99%)

13C = 6 protons, 7 neutrons (stable; about

1% natural abundance)
14C = 6 protons, 8 neutrons (1 ppt or

0.0000000001%; rapidly decays to 14N;

half-life = 5,730 years)
Atomic Mass (NOT mass number)
ATOMIC MASS = the weighted average of
an element’s naturally occurring
isotopes

Carbon Atomic Mass

12C x (0.99) + 13C x (0.01) = 12.011

Chlorine Atomic Mass

35Cl (75.77%) + 37Cl(24.23%) = 35.453
 Atomic Structure - Orbitals
ORBITALS – the space occupied by
electrons circulating around the nucleus

Quantum Mechanical Wave Equation

solution = an orbital (y, psi)

y2 plotted in 3D shows the most likely

space occupied by electrons
 Orbitals
• s, p, d and f orbitals are known
• We are concerned with s and p orbitals
• Orbitals are organized into different layers
(shells) of increasing size and energy
• Different shells (s,p,d,f) contain different
numbers/kinds of orbitals
• Each orbital can hold TWO electrons
 Orbital SHELLS
• The first shell has only an s-orbital (1s)
– The 1S orbital can hold two electrons
– The 1S shell can hold two electrons
• The second shell has an s-orbital and 3 p
orbitals (2s and three 2p orbitals)
– Each orbital can hold two electrons
– The 2s/2p shell can hold 8 electrons in total
• The third shell has one 3s, three 3p and
five 3d orbitals
– This shell can hold 18 electrons in total
 Electronic Energy Levels
3d
3rd Shell can
hold 18 electrons 3p
3s

2nd Shell can 2p

hold 8 electrons 2s

1st Shell can 1s

hold 2 electrons
Orbitals - SHAPE
 p – Orbitals GEOMETRY

Y Y Y
Z Z Z

X X X
2Px 2Py 2Pz
orbital orbital orbital
3 Rules - Electron Configuration
1. Lowest energy orbitals fill up first (1s < 2s < 2p
< 3s <3p <4s <3d)
2. Electrons have spin ( up or down). The 2
electrons in an orbital must have opposite
spins (Pauli exclusion principle).
3. If 2 or more orbitals of equal energy are
available; one electron occupies each with
parallel spin until all are half full (Hund’s rule).
Ground State Configurations
Carbon Ground State Configuration

Element #6

2p
2s

1s
 Chemical Bonding
• Atoms are unhappy if an orbital is half-filled or
empty
• Orbitals can be filled by sharing electrons
between atoms
• 2 Electrons shared between 2 atoms is a single,
chemical bond
• Forming bonds is energetically favored

• Atomic orbitals change into molecular orbitals

when bonds are formed between atoms
The Chemical Bond
Molecular Orbital Theory
 The Nature of the Chemical
Bond
• A Chemical Bond is formed by two
electrons shared between two atoms
• Bonds form because the result is more
energetically favorable
• Energy is released when a bond
forms;
• Therefore energy is needed to
BREAK a bond
 Bonding, Atoms and Molecules
• Chemical bonding forms molecules
• Molecule: Two or more atoms held together by
chemical bonds
• Bonds form by sharing electrons in orbitals
• ATOMIC orbitals shared between atoms yield
MOLECULAR orbitals
• The number of orbitals doesn’t change when a bond
forms; their energy does change:
– BONDING orbital energy goes
DOWN
– ANTIBONDING orbital energy goes
UP
Molecular Orbitals - Illustration

H + H H H

Hydrogen Hydrogen H2
atom atom
molecule
1 electron 1 electron
1 orbital 1 orbital 2 electrons
1 bonding orbital
1 anti-bonding orbital
 Valence Bond Theory
• A covalent bond forms when two atoms
approach closely and ---
• Singly-occupied orbitals on atoms overlap
• The electrons are now paired in the
overlapping orbital and are attracted to the
nuclei of both atoms
The Octet Rule (8 valence e-)
• Orbitals are arranged in shells
• The outer, valence shell is available for
bonding
• Atoms want 8 electrons in their valence
shell.
• Atoms will gain, lose or share to have
8 valence electrons
• The 8 electron rule represents having
one filled s and three filled p orbitals in
the valence shell
 Covalent Bonds
• Atoms share electrons essentially
equally
– Organic molecules form covalent bonds
– Carbon forms covalent bonds with itself
and with hydrogen very readily
• Covalent bonds can be polar (have an
unequal sharing of electrons) but they
are not fully IONIC
How Many Bonds an Element
will form
How to use the Octet Rule
1. ONLY valence shell electrons matter
2. COUNT - left to right using the
Periodic Table
3. Atoms want 8 valence electrons
4. Electrons shared by bonding are
counted for BOTH atoms
5. The octet rule applies to all elements
– H, He, Li and Be only have s orbitals so
their magic number is 2, not 8
 The Periodic Table and
Lewis Structures
• PERIODIC TABLE: indicates how many
electrons are in the valence shell (Group IA have
1, group IIA have 2…) Carbon (Group IVA) has
4 valence electrons
• Sharing electrons through bonding
adds one electron per bond
• Carbon wants to form 4 covalent bonds
to get 8 valence shell electrons.
• Hydrogen (one 1s electron) wants to
form one bond to fill the 1s valence
shell.
 Making Lewis Structures
• Atoms with 1, 2 or 3 valence electrons
form (respectively) 1, 2 or 3 bonds
• Atoms with 4 or more valence electrons
form as many bonds as needed to obey
the octet rule
• The octet rule represents filled s
and p orbitals for the outer
valence shell
Lewis & Line Bond
(Kekule) Structures
Drawing molecules &
chemical bonds
Lewis Structures - Illustration
 Line-Bond (Kekule)
Structures
• Kekule structures substitute a single line
for the electron dots representing a
chemical bond
– The single line represents two electrons
shared between the bonding atoms
– A double line represents four electrons
shared in a double bond (and so forth)
Lewis and Kekule Structures
H H
H C H H C H
H H
Lewis Structure Kekule Structure

H H
H N H N
H H
Lewis Structure Kekule Structure
 Lone Pair Electrons
• Filled orbitals don’t form covalent
bonds
• Filled valence orbitals not used for
bonding are nonbonding or lone-pair
electrons
• Lone-pairs help determine:
– Number of covalent bonds possible
– Obeying the octet rule
• Nonbonding electrons are a filled
orbital - they take up space
Molecular Formula
 Conclusion
• Organic molecules can be drawn as
“stick figures”
• They can also be drawn in a linear
fashion (CH3CH2CH2CH3)
• Most often the “stick figure” is the only
UNAMBIGUOUS way of visualizing the
molecule
• Things get complicated quickly unless
we use the “shorthand” stick figure
views