Overview of Organic Chemistry

INTRODUCTION TO
ORGANIC CHEMISTRY

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Overview of Organic Chemistry

Organic Chemistry

- the chemistry of hydrocarbons

and their derivatives

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 Overview of Organic Chemistry

Carbon-containing but NOT ORGANIC

• Carbon (graphite, diamond)

• CO2
• CO
• CN-
• C-4
• CO3-2

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 Introduction to Pharmaceutical Organic Chemistry

Common Elements in Organic

Compounds

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 Overview of Organic Chemistry

Why study Organic Chemistry?

§ Living things are
made of organic
compounds.
§ Proteins that
make up hair
§ DNA, controls
genetic make-up
§ Foods,
medicines
§ Examine
structures to the
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right
Overview of Organic Chemistry

ELECTRONS AND BONDING

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 Overview of Organic Chemistry

ATOM
• The smallest particle of an element
that maintains its chemical identity
• Building blocks
of atomic structure
– PROTON (p+)
– NEUTRON (n0)
– ELECTRON (e-)
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 Overview of Organic Chemistry

The Nuclide Symbol

"
! 𝐸
• E à Symbol
• A à Mass number
• Z à Atomic number

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 Overview of Organic Chemistry

Question:

• Determine the number of protons,

neutrons and electrons in the following
species.

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 Overview of Organic Chemistry

ELECTRON CONFIGURATION

• “Distribution of
electrons”

• Describes the number

and arrangement of
electrons in orbitals,
subshells and shells
in an atom.
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 Overview of Organic Chemistry

Practice Exercise:
Write the ground-state (stable)
electron configuration of O.

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 Overview of Organic Chemistry

Valence electrons

• Outermost electrons
• Different from charge

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 Overview of Organic Chemistry

Kekulé (Line-Bond) Structure

• have a line drawn between two atoms
indicating a 2-electron covalent bond.

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Overview of Organic Chemistry

MOLECULAR
REPRESENTATIONS OF
COMPOUNDS

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Overview of Organic Chemistry

Molecular Structural Condensed

formula formula structural formula

OH

Partially Condensed Skeletal (Line-angle)

structural formula formula
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 Overview of Organic Chemistry

Molecular Representations
• Molecular formula
– No. of each type of atom

• Structural formula
– Atoms and bonds are shown.

• Condensed structural formula

– Single bond are NOT drawn.
– Groups are clustered.
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 Overview of Organic Chemistry

Sample Exercise:

• Draw the structural and molecular formula

of the given compound.

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 Overview of Organic Chemistry

Skeletal (Line-angle) Structures.

• C and H atoms usually are
NOT shown.
– H atoms attached to all
non-Carbon atoms must be shown.
• Structures are drawn in zigzag
manner. 3H

• Each corner, bent, endpoint, and 3H 3H

intersection represent a C atom. 1H
1H
• C atoms can form 4 covalent 2H
bonds.
Supply the no. of H atoms
mentally.
3H C7 H16
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 Overview of Organic Chemistry

Drawing Skeletal (Line-angle) Structures.

• All heteroatoms (atoms other than carbon and
hydrogen) must be drawn, and any H atoms
attached to a heteroatom must also be drawn.

• Never draw a carbon atom with more than four

bonds.
• Make sure the line connects to bonded atoms. 19
 Overview of Organic Chemistry

Sample Exercise:

• Draw the line-angle structure of

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 Overview of Organic Chemistry

Sample Exercise:

• Write the molecular formula of the given

structure.

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 Overview of Organic Chemistry

Practice Problem:
• Identify whether the transformation below
involves an increase, a decrease or no change in
number of hydrogen atoms

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Overview of Organic Chemistry

ELECTRONEGATIVITY AND
BOND POLARITY

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 Overview of Organic Chemistry

Nature of Chemical Bonds

• Atoms form bonds because the compound

that results is more stable than the
separate atoms. (OCTET RULE)

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 Overview of Organic Chemistry

Nature of Chemical Bonds

• Ionic bonds form as a result of electron

transfer.

• Covalent bonds form due to sharing of

electrons.

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 Overview of Organic Chemistry

Nature of Chemical Bonds

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 Overview of Organic Chemistry

Bond Polarity and Electronegativity

• Covalent bonds can have ionic character.

• Covalent bonds differ on degree of sharing.

– Depends on difference of electronegativity

• ELECTRONEGATIVITY
– ability of an atom to attract the shared
electrons in a covalent bond
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 Overview of Organic Chemistry

Periodic Table and Electronegativity

INCREASING ELECTRONEGATIVITY

ELECTRONEGATIVITY
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 Overview of Organic Chemistry

Classification of Chemical Bonds

DIFFERENCE TYPE OF BOND MOST LIKELY
IN EN FORMED BETWEEN

Less than 0.5

Two Nonmetals OR
Nonmetal and Metalloid
0.5 – 1.9

More than 1.9 Metal + Nonmetal

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 Overview of Organic Chemistry

Sample Question:
Identify the type of bond the exist
between:
a) O-H
b) N-H
c) Na-F
d) C-Mg

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 Overview of Organic Chemistry

Electrostatic Map Potential

• a.k.a. Electron
Density Model

• Arrows indicate
direction of bond
polarity

• Bond Dipole Arrow

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 Overview of Organic Chemistry

Electrostatic Map Potential

• Bonding electrons toward electronegative atom
– C acquires partial positive charge, d+ (delta plus)
– Electronegative atom acquires partial negative
charge, d- (delta minus)

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 Overview of Organic Chemistry

Sample Problem:
Using a bond dipole arrow and the symbols
d+ and d-, indicate the direction of polarity in
these bonds.

a) C – H

b) N – H

c) C – O
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Overview of Organic Chemistry

FORMAL CHARGE

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 Overview of Organic Chemistry

Formal Charge

• The charge on an atom in a molecule or

polyatomic ion

𝑭𝑪 = # 𝒐𝒇 𝒗𝒂𝒍𝒆𝒏𝒄𝒆 𝒆! − 𝑼𝒏𝒔𝒉𝒂𝒓𝒆𝒅 𝒆! − # 𝒐𝒇 𝒃𝒐𝒏𝒅𝒔

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 Overview of Organic Chemistry

Example:
Consider the nitrogen atom in the
structure shown and determine if it
has a formal charge.

𝑭𝑪 = # 𝒐𝒇 𝒗𝒂𝒍𝒆𝒏𝒄𝒆 𝒆! − 𝑼𝒏𝒔𝒉𝒂𝒓𝒆𝒅 𝒆! − # 𝒐𝒇 𝒃𝒐𝒏𝒅𝒔

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 Overview of Organic Chemistry

Practice Exercise:
Given the structure of H3O+ and show
which atom bears the formal charge.

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 Overview of Organic Chemistry

Practice Exercise:
Given the structure of CH3O- and show
which atom bears the formal charge.

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Overview of Organic Chemistry

HYBRIDIZATION OF
s AND p ORBITALS:
sp3, sp2, and sp Orbitals

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 Overview of Organic Chemistry

Predicting Bond Angles and

Molecular Shapes
• Valence-Shell Electron Pair Repulsion
(VSEPR)
– Valence electrons may be involved in the
formation of single, double or triple bonds

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 Overview of Organic Chemistry

Electron
Density around Bond
Type of Bond Shape
the Central angle
Atom
Single Bond

Double Bond

Triple Bond

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Overview of Organic Chemistry

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 Overview of Organic Chemistry

Valence Bond Theory

• Electrons are paired in the overlapping
orbitals and are attracted to nuclei of both
atoms.

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 Overview of Organic Chemistry

Hybridization of Atomic Orbitals

• Atomic orbitals combine to form new

orbitals called HYBRID ORBITALS.

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 Overview of Organic Chemistry

Sigma (s) bond and Pi (p) bonds

• Electrons in the s bond are centered
between nuclei.

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 Overview of Organic Chemistry

Sigma (s) bond and Pi (p) bonds

• Electrons in the p bond occupy regions
above and below the axis joining the nuclei.

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 Overview of Organic Chemistry

Groups
Type of
Bonded Orbital Predicted
Example Bonds to
to Hybridization Bond angle
Carbon
Carbon
Single Bond

Double Bond

Triple Bond

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Overview of Organic Chemistry

BOND LENGTH AND

BOND STRENGTH

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 Overview of Organic Chemistry

Bond Strength (Bond Energy)

• Energy needed to break or form a

chemical bond

(s) bonds > (p) bonds

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 Overview of Organic Chemistry

Bond Length
• Optimum distance between nuclei
leading to maximum stability

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