B. Eng. (Hons.

) Chemical Engineering

Physical and Organic Chemistry

Introduction to Organic Chemistry:

Structure and Bonding

PowerPoint® Slides
by Nazlina
 Learning Outcome(s)

1. Able to differentiate between organic and inorganic

compounds,
2. Able to classify chemical compounds to organic or inorganic,
3. Able to sub-classify organic compounds into closed, open,
alicylic, aromatic or heterocylic groups,
4. Able to derive empiric and molecular formulae given any
organic structures, and
5. Able to draw an organic molecules using Kekulé, condensed
and skeletal structures techniques.

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 Definition of Organic Chemistry

• The chemistry of the compounds of carbon.

• A field of immense importance to technology.
• A chemistry of dyes and drugs, paper and ink, paints and
plastics, gasoline and rubber tires.
• Able to identify types of chemical bonding in organic
compounds,

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 Organic Chemistry in Industry

Field of Applications Organic Compounds Used

Petroleum Gasoline, lubricants, cooking gas,

solvents, etc.
Dyes Phenol
Explosive Materials Trinitrotoluene (TNT)
Food Glucose, Monosodium Glutamate
(MSG)
Cosmetic and Paracethamol, Isopropyl
Pharmaceutical palmitate

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 Dissimilarities Between Organic and Inorganic
Compounds
• Chemical compounds are divided into two classes;
ORGANIC and INORGANIC, depending upon where
they come from.
• Inorganic compounds are those obtained from minerals.
• Organic compounds are those obtained from sources,
that is, from materials produced by living organism.
• Now, organic compounds are sometime synthesized,
too.

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 Dissimilarities Between Organic and Inorganic
Compounds (Cont.)
Organic Inorganic
Compounds Compounds
Physical Properties Easily flammable, Inflammable,
insoluble in water dissolve in water
Bonding Type Covalent Ionic
Reactivity i. Show slow i. High reaction
reaction rate. rate.
ii. Need external ii. Reaction are
energy to break able to take
its covalent place at room
bond. temperature.
iii. Consume iii. Catalyst is not
catalyst. used.

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 Classification of Chemicals Compounds

Chemical
Compounds

Organic Inorganic
Compound Compounds

Chemically
Living Chemically
Minerals Synthesize
Organisms Synthesized
d

From Inorganic
Petroleum Plant Coal From Organic Substances
Substances

Carboxylic
Alcohols Carbonates Cyanides
acids

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 Classification of Organic Compounds: Upon
Ring Structures

Organic
•

• Compounds

• Opened • Closed Ring

Ring
• Unsaturat • Heterocyli
• Saturated • Alycylic • Aromatic
ed c
• Compoun • Compoun • Compoun
• Compoun • Compoun
ds ds ds
ds ds

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 Classification of Organic Compounds: Upon
Ring Structures (Cont.)
Opened Form of
Organic Compounds

Saturated Unsaturated
Compounds Compounds
Do not consist Contain of
CH3CH2CH3,
of double and/or double and/or
Propane
triple bonds. triple bonds.

CH2=CH2, CH≡ CH,

Ethene Ethyne

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 Classification of Organic Compounds: Upon
Ring Structures (Cont.)

Closed Form of
Organic Compounds

Alycylic Aromatic Heterocylic

Benzene rings
Do not Contains of
contain of
contains of benzene
one of the
benzene ring
elements;
ring
S, N or O

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 Classification of Organic Compounds: Upon
Ring Structures (Cont.)

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 Compulsory page

Classification of Organic Compounds Upon

Functional Groups
• Charles-Frédéric Gerhardt (1816-1856), a French chemist,
devised an early useful understanding of organic
compounds classification. Through his ideas, a more
comprehensive method has been utilized to organize the
organic compounds classification. They are based on:
i. Functional group: a group of atoms within a molecule that
has a characteristic chemical behavior, highly reactive and
readily go for chemical reaction.
ii. Residue: a group of atoms within a molecule which is not
reactive and not ready for any chemical reaction.
iii. Homologous series: a series of compounds in which each
member differ from the next member by a constant amount.

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 Classification of Organic Compounds Upon
Functional Groups (Cont.)

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 Functional Groups

• A functional group is an atom or a group of atoms with

characteristic chemical and physical properties. It is the
reactive part of the molecule .
• Most organic compounds have C—C and C—H
bonds .However, many organic molecules possess other
structural features :
Heteroatoms —atoms other than carbon or
hydrogen .These structural features distinguish one
organic molecule from another.They determine a
molecule’s geometry, physical properties,

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 Functional Groups

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 Functional Groups

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 Functional Groups

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 Bonding of Organic Compounds: Types of
Chemical Bonds
• Covalent bond: Formed when two elements share
valence electrons so that both gain full valence shells.
Bonds can be single (two shared electrons), double
(four shared electrons), or triple (six shared electrons).
• Ionic bond: Formed when the electro negativities of the
bonded atoms are significantly different. Both shared
electrons are almost completely associated with the
more electronegative atom, which becomes an anion
(negatively charged) while the other atom becomes a
cation (positively charged).

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 Bonding of Organic Compounds: Types of
Chemical Bonds (Cont.)
Source: Organic
Chemistry 1: Bonding in
Organic Compounds
(2009). In Sparknotes.
Retrieved September 14,
2009, from Sparknotes:
http://sparkcharts.sparkn
otes.com/chemistry/orga
nicchemistry1/section1.p
hp

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 Bonding of Organic Compounds: Hybridization

• Hybridization: Formation of hybrid orbitals, which are

mixtures of individual atomic orbitals.
• The number of atomic orbitals used to create a set of
hybrid orbitals equals the number of orbitals generated
by hybridization.
• Hybrid orbitals can hold up to two electrons; half-filled
hybrid orbitals can share electrons with other half filled
orbitals to form a covalent bond.
• Sigma (σ) bonds: Bonds formed by the head-on overlap
of sp, sp², or sp³ hybrid orbitals with each other or with
hydrogen 1s orbitals.
• Pi (π) bonds: Bonds formed by the sideways overlap of
p orbitals.

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 Types of Covalent Bond

• There are three types of covalent bond depending upon

the number of shared electron pairs.
• SINGLE COVALENT BOND: A covalent bond formed by
the mutual sharing of one electron pair between two
atoms is called a "Single   Covalent bond."  It is denoted
by single short line, –.
• DOUBLE COVALENT BOND: A covalent bond formed
between two atoms by the mutual sharing of two electron
pairs is called a "double   covalent bond". It is denoted
by double short line, ═.
• TRIPLE COVALENT BOND: A covalent bond formed by
the mutual sharing of three electron pairs is called a
"Triple covalent bond". It is   denoted by triple short line,
≡.

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 Types of Covalent Bond (Cont.)

• POLAR COVALENT BOND: A covalent bond formed

between two different atoms (having different
electronegativity) is known as polar covalent bond. For
example when a covalent bond is formed between H and Cl
, it is polar in nature because Cl is more   electronegative
than H atom . Therefore, electron cloud is shifted towards Cl
atom. Due to this reason a   partial -ve charge appeared on
Cl atom and an equal +ve charge on H atom.
• NON-POLAR BOND: A covalent bond formed between two
like atoms is known as non-polar bond. Since the difference
of electronegativity is zero therefore, both atoms attract
electron pair equally and no charge appears on any atom
and the whole molecule becomes neutral.

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 Empirical and Molecular Formula of Organic
Compounds
• Empirical formula expresses the relative proportions of
atoms in a molecule as smallest whole numbers.
• Molecular formula gives the total number of each kind
of atom in a molecule.
Molecular Formula = n (Empirical Formula)
• Some compounds share empiric and molecular formula.
• But, many organic compounds has otherwise.

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 Empirical and Molecular Formula of Organic
Compounds (Cont.)

Organic Empirical Formula Molecular Formula

Compounds
Methane CH4 CH4

Ethane CH3 C2H6

Ethyne CH C2H2

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 Drawing Organic Molecules
Condensed Structure
• In the condensed structural formula, each carbon atom is

written separately and following each carbon atom are

listed the other atoms that are bonded to that carbon
atom.
• This structure does not show single bonds between

carbon and hydrogen atoms but double and triple bonds

are shown

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 Drawing Organic Molecules
Condensed structure (cont’d)

CH3CH2CH2CH3 CH3CHCH3CH3
or or
CH3(CH2)2CH3 CH(CH3)3

C3H6 C4H6

or or
CH2 = CHCH3 CH3C CCH3

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 Drawing Organic Molecules

Skeletal structure
• In skeletal structure, the hydrogen atoms attached

directly to carbons are removed, leaving just a carbon

skeleton with functional groups attached to it.

• Ethane Skeletal structure

C2H6
Propane
C3H8
Propene
C3H6
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 Drawing Organic Molecules
Skeletal structure (cont’d)

Methylbutane Skeletal structure

C5H12

H
Methanamine
CH3NH2 N H
O
Ethanoic Acid H
C2H4O2 O

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 Drawing Organic Molecules

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 Drawing Organic Molecules

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 Drawing Organic Molecules
Kekulẻ Structure

• Kekulẻ suggested structure of benzene which contained

six-membered ring of carbon atoms with alternating
single and double bond.

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 Drawing Organic Molecules

Kekule Structure (cont’d)

The circle in the middle shows the delocalised system of

electrons in benzene ring.

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 Drawing Organic Molecules
3D Chemical Structure

• Molecules are 3D structure so it is always accurate to

describe them in 3D

• Sketching a molecule in 3D will include information

about:
- Bond angles
- Shapes of molecules
- Isomers

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 Drawing Organic Molecules

• A 3D representation of a chemical structure uses a:

Types of line Styles Indications

used
Normal bond Bond lies in the
plane of paper
Dashed bond Bond pointing to
the back of the
paper
Wedged bond Bond pointing
forwards, towards
the viewer

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 Drawing Organic Molecules

Source:http://www.ivy-rose.co.uk/Chemistry/Organic/How-to-draw-organic-
molecules-in-3D.php

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 Drawing Organic Molecules

Propane 3D structure of propane

Ethanoic acid 3D structure of ethanoic acid

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 Class Activity

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 Compulsory page

References:

1. McMurry, John. (2008). Organic Chemistry. International

Student Edition. 7th Edition. Thomson Learning Brooks/Cole,
pp. 3-27.
2. Charles Gerhardt. (2009). In Encyclopædia Britannica.
Retrieved September 14, 2009, from Encyclopædia
Britannica Online:
http://www.britannica.com/EBchecked/topic/230539/Charles-
Gerhardt

3. Organic Chemistry 1 (2009). In Sparknotes. Retrieved

September 14, 2009, from Sparknotes Online:
http://sparkcharts.sparknotes.com/chemistry/organicchemistr
y1/
4. Types of Covalent Bond (2009). In City Collegiate. Retrieved
September 14, 2009, from City Collegiate:
http://www.citycollegiate.com/bondIXd.htm
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 Compulsory page

Key Terms:
Term Definition
IUPAC Nomenclature

Molecular Structure

Open Ring

Closed Ring

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