CHAPTER 1 : INTRODUCTION

TO ORGANIC CHEMISTRY
The study of the composition of
matter and the changes it undergoes
The study of the composition of
matter and the changes it undergoes
IS THIS WHAT
YOU THINK?
The study of the composition of
matter and the changes it undergoes
Chemistry is Life


Can you identify organic compounds from this
picture?
1. Road
surface
(bitumen)
2. Fuel in car
3. Tyre

What is Organic
chemistry?

TOPIC 1.1
Chemistry of Carbon


Inorganic Organic
Some Brief History
Mr Friedrich Whler
Born: 31-Jul-1800
Birthplace: Eschersheim, Germany
Died: 23-Sep-1882
He changed the belief that organic
compounds could only be made by living
things.
Organic compounds are compounds that
contain the element Carbon (C).
Most organic compounds also contain
hydrogen (H).
Organic compounds that contain only carbon
and hydrogen are called hydrocarbons.



Q: Do all compounds containing carbon
considered as organic compounds?

A: No. Chemists consider carbonates and oxides
of carbon as INORGANIC compounds rather
than organic.




Question Time!

Organic chemistry is the chemistry of
carbon compound.
Basic for all life.
Example :
methane, DNA, urea, DDT (insecticide),
penicillin , nicotine, aspirin etc..

But not all carbon compounds are organics.

Example :
carbonate (CO
3
2-
), cyanide (CN
-
), bicarbonate (HCO
3
-
), carbon
dioxide (CO
2
) and carbon monoxide (CO).

What is organic chemistry?
Why is it so important?
Think about how organic compounds affect our daily life:
Our clothes natural and synthetic fibers
Our medicines
Our food carbohydrates, proteins, triglycerides
Oils, perfumes, paints, plastics, detergents, etc.
11
Organic Compounds
Typical organic compounds

have covalent bonds.
have low melting points.
have low boiling points.
are flammable.
are soluble in non-polar
solvents.
are not soluble in water.
12
Some organic chemicals
DNA
Materials
Essential oils
Fuels
Pigments
13
Organic vs. Inorganic
Propane, C
3
H
8
, is an organic
compound used as a fuel.

NaCl, salt, is an inorganic
compound composed of Na
+

and Cl
-
ions.


14
Comparing Organic and Inorganic
Compounds
Property Organic compound Inorganic compound
Bonding with molecule Usually covalent Often ionic
Forces between
molecules
Generally weak
(Intermolecular force)
Quite strong
(Electrostatic force)
Normal physical state
Gases, liquids or low-
melting-point solids.
Usually high-melting-
point solids.
Flammability Often flammable Usually nonflammable
Solubility in water Insoluble Soluble
Conductivity Nonconductor Conductor
Rate of chemical
reaction
Slow and complex Fast and simple
15
Naturally Occurred Organic Compounds
Name Of Organic
Compounds
Origin Usage
Proteins
Example :
a) Enzymes
b) Hormones
From animals a) As a structural materials.
b) As a biological catalyst
and regulators.
Fats and Oils
Example :
a) Triglyceride b)
Paraffin Oils c)
Almond Oils
From animals
and vegetables
To store energy.
Vitamins
Example :
A,B Complex, C, D,
E and K
From food For healthy growth and
functioning.
Synthetic Organic Compounds
Items Examples Usage
Plastics Poly (ethene),
Perspex.
For packaging, plastic
bags, as a substitute for
glass.
Medicines
and
Drugs
Tranquilizer,
Analgesic and
Bactericide.
To treat tropical diseases
such as Trypanosomiasis
or Sleeping Illness and
Malaria.
Pesticides Dichlorodiphenyl
trichloroethane
( DDT )
To kill houseflies and
other insects.
Dyes Methylene blue Give colour to the material.

C
Why carbon?
o A carbon atom forms four bonds
oCarbon atoms form stable bonds with
other carbon atoms (i.e., the CC
covalent bond is strong)
oCan form chains and even networks
oExamples: graphite and diamond
carbon
6
12.011

C

Why carbon?
carbon
6
12.011

Basic for all life
Form stable covalent bonds to other
carbon atoms catenation
Can form single, double, triple bonds
Long carbon chain can be produced
Will bond to many other element
A huge number of chemicals are possible
Position of Carbon


Chemical Formulas
Organic compounds can be complex
A system is needed that shows structure.
We want something that is easy to read.
Molecular formula
Empirical formula
Structural formula
Condensed formula
Bond-line formula


Molecular formula
Actual number of atoms of each element in a
molecule.

Empirical formula
Simplest ratio number of atoms of each
element in a molecule.

Example: Glucose, C
6
H
12
O
6

C
6
H
12
O
6
Molecular formula
CH
2
O
Empirical formula


Learning Check!
1. Write the emperical formula for the following molecules:

(a) glucose, C
6
H
12
O
6
(b) Benzene, C
6
H
6
(c) Oxalic acid, C
2
H
2
O
4

2. After exercise, lactic acid is formed in the muscles, making a person tired. An
analysis shows that lactic acid contains 40.0% C, 6.71% H & 53.5% O by
weight
(a) Calculate the emperical formula of lactic acid.
(b) Calculate the molecular formula of lactic acid
[Mr of lactic acid is 90.08; C:12 , H:1 , O:16]



Expanded @ Structural Formula
Show all atoms in the bonds
Bonds represents as lines
Examples:

Propane


Condensed Structural Formula

A Type of line format
Shorthand way of writing formula
List of atoms in order and tells how there are bound
together
Example:

Propane
CH
3
CH
2
CH
3



Bond Line @ Skeleton Formula



Represent structure by showing bonds
between carbons and atoms other than
hydrogen.
Atoms other than carbon and hydrogen are
called heteroatoms.
Example
CH
3
CH
2
CH
2
CH
3
is shown as
CH
3
CH
2
CH
2
CH
2
OH

is shown as


OH
Learning Check!
C C H H
H H
H H
C
2
H
6

Molecular formula
CH
3

Empirical formula
CH
3
CH
3

Condensed formula Structural formula
Example: Ethane

Learning Check!
Structural formula
Example: Pentane

C
H
H
H
C C
H
H H
H H
C C
H H
H H
C
5
H
12
Molecular formula
CH
3
(CH
2
)
3
CH
3
or
CH
3
CH
2
CH
2
CH
2
CH
3

Condensed formula

Bond-line formula
Learning Check!
A. Write the condensed formula for:
H H H H H

H C C C C C H

H H H H H
B. What is its molecular formula?
(Gives total # of each atom, does not indicate how they are arranged)
C. What is its name?



TOPIC 1.2 :
Types of Organic Compound


Types of Organic Compound
ORGANIC COMPOUND
ALIPHATIC ALICYCLIC AROMATIC
OPEN chains of carbon atoms.
Unbranched or Branched
Contain Single, Double or Triple
bonds.
Example:
ethane (CH
3
CH
3
)
ethene / ethylene (CH
2
=CH
2
)
ethyne / acetylene (CHCH)
CLOSE rings of carbon
Atoms.
Rings form the shape
of POLYGON (triangle,
square, rectangle or
etc).
CLOSE rings of carbon
atoms.
Contain a benzene
ring.
Example: Benzene


Types of Organic Compound
ORGANIC COMPOUND
ALIPHATIC
SATURATED UNSATURATED
Compound that contains only
single bond.

Example: alkane
Compound that contains
multiple bond.

Example: alkene, alkyne
C C
H H
H H
H H
C C
H H
H H
HC CH
TOPIC 1.3 :
Types of Reaction
Type of Organic Reaction
General
Addition Substitution Elimination Rearrangement
Specific
Hydrogenation Esterification Oxidation Hydrolysis
34
General Reaction
35
Type of Organic Reaction: Addition
Two substances react together to form a single substance.
Addition of HBr to an alkene
Hydrogen
Bromide
Ethane Bromoethane
36
Type of Organic Reaction: Substitution
An atom or a group (leaving group) in a molecule is replaced by
another atom or group (nucleophile / electrophile).
S
N
2 reaction
Hydroxide ion (nucleophile)
(leaving group)
Bromobutane Butanol Bromide ion
37
Type of Organic Reaction: Elimination
Removal of atoms or groups of atoms from a saturated
molecule to form an unsaturated molecule.
Dehydration of alcohol
CH
3
CH
2
CH
2
CH
2
OH
Butanol
H
2
SO
4

CH
3
CH
2
CH=CH
2
+ H
2
O
Butene
38
Type of Organic Reaction: Rearrangement
Migration of an atom, a group of atoms or a bond from one
atom to another within molecule to form its isomer.
Tautomerism of keto-enol
CH
3
C CH
2

OH

Propenol
CH
3
CCH
3

O

Propanone
39
Specific Reaction
40
Type of Organic Reaction: Hydrogenation
Addition of hydrogen to a multiple bond to form a single bond
substance.
Hydrogenation of alkane
41
Type of Organic Reaction: Esterification
Acid-catalyzed ester formation between alcohol and
carboxylic acid.
Fischer esterification
CH
3
COCH
2
CH
3

O
+ H
2
O
CH
3
COH
O
+
CH
3
CH
2
OH
H
2
SO
4

reflux
Ethanoic acid Ethanol
Ethyl ethanoate
42
Type of Organic Reaction: Oxidation
An increase in the number of bonds between carbon and oxygen
and/or a decrease in the number of carbon-hydrogen bonds.

Oxidation of methane
CH
4
2O
2
+
CO
2

2H
2
O
+
Methane
Oxygen
Carbon dioxide
Water
43
Type of Organic Reaction: Hydrolysis
Chemical process in which a molecule is split into two parts
by the addition of a molecule of water.
(CH
3
)
3
CBr + H
2
O (CH
3
)
3
COH + HBr
tert-Butyl bromide
tert-Butyl alcohol
Hydrogen
bromide
44
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