INTRODUCTION TO

ORGANIC CHEMISTRY

TOPICS
1.1
1.2
1.3
1.4
1.5
1.6
1.7
1.8
1.9

Introduction to Organic Chemistry

Alkanes and Cycloalkanes
Alkenes and Alkynes
Aromatic Compounds
Alkyl Halides
Alcohols
Aldehydes and Ketones
Carboxylic Acids and their Derivatives
Amines

INTRODUCTION TO ORGANIC
CHEMISTRY
Structural Formulas of Organic Molecules
Ways of Depicting the Organic Molecules
Classification of Carbon and Hydrogen
Atoms in Organic Molecules
Functional Groups and Homologous
Series
Isomerism in Organic Molecules
Introduction to Organic Molecules
Reactions

1.1 Introduction to Organic Chemistry

Organic chemistry is a branch of chemistry
that focuses on compounds that contain
carbon
except CO, CO2, carbonates, and carbides

Even though organic compounds only

contain a few elements, the unique ways
carbon atoms can attach together to form
molecules leads to millions of different
organic compounds

1.1 Introduction to Organic Chemistry

Organic compounds tend to be molecular

Mainly composed of just six nonmetallic elements

C, H, O, N, S, and P
Contains halides group- organohalides

Unique things about carbon atom

- can form four bond
- bond is very strong and nonreactive
- can form long chains
- can form rings
- bond formed with single, double, or triple
bonds

1.1 Introduction to Organic Chemistry

Properties
Compounds found in all three states
- solids, liquids, and gases
- solids tend to have low melting points

Solubility in water varies depending on which of the

other elements are attached to C and how many there
are
- CH3OH is miscible with water; C10H21OH is insoluble

Hydrophobic part
6

1.1 Introduction to Organic Chemistry

Bonding and Hybridization

sp3

When C has four single bonds, the shape is

tetrahedral, carbon sp3

1.1 Introduction to Organic Chemistry

Bonding and Hybridization

sp2

When C has two single + one double bond, the

shape is trigonal planar, carbon sp2

1.1 Introduction to Organic Chemistry

Bonding and Hybridization

sp

When C has one triple + one single or two

double bonds, the shape is linear, carbon sp

Structural Formulas of Organic

Molecules
Molecular Formula tells us what are the
elements and how many atoms of each
element are present in one molecule
For example
C2H7N
C3H8O

Structural Formulas of Organic

Molecules
Structural Formula tells us the actual
number of atoms and shows the order in
which the atoms in the molecule are
connected together
For example C2H7N and C3H8O
H H H

H H H

H C C N H

H C N C H

H H
Formula I : Ethanamine

Formula II : Dimethylamine

H H H

H C C C O H
H H H
Formula I :1-Propanol

H H

H C O C C H
H

H H

Formula II : Methoxyethane

Ways of Depicting the Organic

Molecules
Expanded structural formula shows every
atom and type of covalent bond in the
molecule
H H O
H C C C O H
H H

H H H
H C C C
H

H C C C C H
H

Ways of Depicting the Organic

Molecules
Condensed structural formula shows every
atom and type of covalent bond in the
molecule
H H O
H C C C O H

CH3CH2COOH

H H
H H H H H H
H C C C C C C H
H

H H H

CH3CH CH(CH2)2CH3

Ways of Depicting the Organic

Molecules
Skeletal structural formula shows the
carbon skeleton, the atom hydrogen omitted
on carbon, unless hydrogen bound to the
O
heteroatoms.
H H O
H C C C O H
H H

OH
C H
C
H
C
C
H
H
C
H
H
H

OH

OH

H H
H H H H
H C C C C H
H

H H H H
H C C C N H
H H H

NH2

Ways of Depicting the Organic

Molecules
Skeletal structural formula in 3D 3D
geometry of atoms spatial arrangements
of atoms or groups of atoms within the
molecule. Wedges and dashes to indicate 3D
solid line represent a group
lying in the plane of paper

Cl
Cl

dash represent a group

going behind of the plane
of paper

Cl

HO
HO

OH

wedge represent a group

coming out of the plane
of paper

Exercise 1 : Write the expanded structural and

condensed formula for the straight chain alkane C8H18
Exercise 2 : Write the molecular formula and condensed
structures for each of the following compounds

Exercise 3 : Write the carbon skeletal for compounds

below
Br
CH3CH2CHCHCCH2COOH
OH

Classification of Carbon and Hydrogen

Atoms in Organic Molecules
Primary carbon one alkyl group and three atoms
hydrogen
Secondary carbon two alkyl groups and two atoms
hydrogen
Tertiary carbon three alkyl groups and one atom
hydrogen
Quarternary four alkyl groups and no atom
hydrogen

Classification of Carbon and

Hydrogen Atoms in Organic Molecules
Primary hydrogen three atoms hydrogen attached
to primary carbon
Secondary hydrogen two atoms hydrogen
attached to secondary carbon
Tertiary hydrogen three atoms hydrogen attached
to tertiary carbon

Exercise 4 : Identify the carbon atoms in the following

molecules as primary, secondary, tertiary or quaternary
CH3

CH3

CH3CHCH2CCH3
CH3
(a)

(b)

Exercise 5 : Identify the hydrogen atoms on the above

molecules as primary, secondary, or tertiary

Functional Groups and

Homologous Series
Functional groups is a group of atoms that
have a chemical behaviour of the parent
molecule.
is the structural unit responsible for a
given
molecules
reactivity under a
particular set of conditions.
The group reacts in a typical way, generally
independent of the rest of the molecule

1.1 Introduction to Organic Chemistry

Functional Groups
Class

Functional
Group

Example
CH3

Alkene

C C

H3C

CH2

Limonene

1.1 Introduction to Organic Chemistry

Functional Groups
Class

Functional
Group

Example
OH C
CH3 C

Alkyne

C C

Norethindrone

1.1 Introduction to Organic Chemistry

Functional Groups
Class

Functional
Group

Example
Cl

Alkyl Halide

R X
X = F, Cl, Br, I

Cl

Cl

Cl

Cl
Cl

1,2,3,4,5,6-Hexachlorocyclohexane
Lindane

1.1 Introduction to Organic Chemistry

Functional Groups
Class

Alcohol

Functional
Group

Example
CH3

R OH
OH
H3C

CH3

2-Isopropyl-5-methylcyclohexanol
Menthol

1.1 Introduction to Organic Chemistry

Functional Groups
Class

Functional
Group

Example
HO

(CH2)4CH3

H3C
Ether

R O R'

O
9

H3C CH3
-Tetrahydrocannabinol

THC

1.1 Introduction to Organic Chemistry

Functional Groups
Class

Functional
Group
O

Aldehyde
R

Example
H

C
H

Cinnamaldehyde

1.1 Introduction to Organic Chemistry

Functional Groups
Class

Functional
Group

Example
CH3

O
O
Ketone
R

R'
CH3
Jasmone

1.1 Introduction to Organic Chemistry

Functional Groups
Class

Functional
Group

Example
CH3

Carboxylic
Acid

O
R

CH3

OH

CH3
Ibuprofen

OH

1.1 Introduction to Organic Chemistry

Functional Groups
Class

Functional
Group

Example
O

O
Ester
R

C
O

R'

OH
Methyl salicylate

CH3

1.1 Introduction to Organic Chemistry

Functional Groups
Class

Functional
Group

Example
H3CO

Amine

N
R'

R"

NH2

H3CO
OCH3
Mescaline

Functional Groups and

Homologous Series
Differences between functional groups and
class of compound they are not the same!
For example : 2-butanol functional group is
(-OH) hydroxyl group .But the class of the
compound is alcohol.

OH
CH3CH2CHCH3

Functional Groups and

Homologous Series
Differences between functional groups and
class of compound they are not the same!
For example : Propanal and propanone
functional group is (C=O) carbonyl group.
But the class of the compound is aldehyde
and ketone respectively

H3CH2C

H3C

CH3

Exercise 6:

i) Draw any three chain isomers of C7H16

ii) Draw any two positional isomers of C5H12O

iii) Draw any one functional isomers of C5H12O

33

Functional Groups and

Homologous Series
Homologous series a series of organic
compounds
with
similar
chemical
properties, in which each member differs
from previous one by the addition of a CH2group is called a homologous series
The members of a homologous series are
called homologues.

Functional Groups and

Homologous Series
General properties
- same functional groups and similar chemical
properties
- each member differs from next in the series
by a CH2 group
- can be prepared by similar methods
- physical properties is progressive change
with increasing molecular mass
- contain the same elements and represented
by the same general formula

Functional Groups and

Homologous Series
General formula - a general formula is a
formula that can apply not only to a specific
compound but to all compound in the same
homologous series.
Some homologous series have the same
general formula
- Alkenes and cycloalkanes (CnH2n)
- Alkynes and cycloalkenes (CnH2n-2)
- Aldehydes and ketones (CnH2nO)
- Carboxylic acids and esters (CnH2nO2)

Functional Groups and

Homologous Series
Homologous
series

General
Formula

Example

Structural
Formula

Alkanes

CnH2n+2

C6H14

CH3(CH2)4CH3

Alkenes

CnH2

C6H12

CH3(CH2)3CH=CH2

Alkynes

CnH2n-2

C 3H 4

CH3C CH

Haloalkanes

CnH2n+1X

C3H7 Br

CH3CH2CH2Br

Alcohols

CnH2n+2 O

C3H7 OH

CH3CH2CH2OH

Aldehydes

CnH2n O

C 4H 8 O

CH3CH2CH2CH=O

Ketones

CnH2n O

C4H8 O

CH3CH2C=OCH3

Carboxylic acids

CnH2n O2

C3H6 O2

CH3CH2COOH

Esters

CnH2n O2

C3H6 O2

CH3COOCH3

Amine

CnH2n+1NH2

C3H7 NH2

CH3CH2CH2NH2

Isomerism in Organic Molecules

Isomerism - two or more organic compounds
with same molecular formula but different
arrangements of atoms in space within the
molecules.
Two main types
Structural or constitutional isomerism
Stereoisomerism

See page 77 - 81

Isomerism in Organic Molecules

Isomerism

Constitutional
Isomerism

Chain
Isomerism

Positional
Isomerism

Stereoisomerism

Functional
Isomerism

Geometrical
Isomerism

Optical
Isomerism

Isomerism in Organic Molecules

Constitutional or Structural isomerism molecules have same molecular formulae
but different structural formulae
Divided into three types

See page 77 - 81

Isomerism in Organic Molecules

Constitutional Isomerism
Divided into three types
i) Chain isomers - different structural formulae due to
varying lengths in its carbon chains or carbon
skeletons. The length of carbon chains can be altered
due to branching.

H H H H
H C C C C H
H H H H
n-butane
(Unbranched)
See page 77 - 81

H
H C H
H
H
H C C C H
H H H

Isobutane
(Branched chain)

41

Isomerism in Organic Molecules

Constitutional Isomerism
ii) Positional isomers - molecules have same

carbon chain and functional groups but

differ in the position of the functional group
H H H H

H Br H H

H C C C C Br

H C C C C H

H H H H

H H H H

Bromobutane

See page 77 - 81

2-Bromobutane

Isomerism in Organic Molecules

Constitutional Isomerism
iii) Functional isomers - molecules have
different functional groups, hence their
structural formulae are different.
H H O

H O H

H C C C H

H C C C H

H H
Propanal

See page 77 - 81

Propanone

Isomerism in Organic Molecules

Possible structural isomers of alkanes
Carbon Molecular Formula
Chains
4
C4H10
5
C5H12
6
C6H14
7
C7H16
8
C8H18
9
C9H20
10
C10H22

Possible
Isomers
2
3
5
9
18
35
75

Isomerism in Organic Molecules

Rotation about a bond is NOT isomerism

See page 77 - 81

Isomerism in Organic Molecules

Stereoisomerism - molecules have same
molecular formulae and structural formulae
but different orientation of atoms and bond
in space within the molecules

Isomerism in Organic Molecules

Divided into two types
Geometrical isomers have the same
molecular formula but a different orientation
in space that cannot be overcome by
rotation around a sigma bond
Geometric isomers occurs if the presence
of a carbon-carbon double bond or a ring
structure in its molecule
Double bond between two carbon atoms, the
central sigma bond is sandwiches by a pi
bond above and below. This pi bond
prevents the rotation of the carbon atoms.

Isomerism in Organic Molecules

Geometrical isomers
H3C

CH3

H
C C

C C
H

Cis-2- butene

H3C
H

H
H

CH3

CH3
H

Cis-1,2-dimethylcyclopropane

H3C

Trans-2- butene

H3C
H

H
H
H

CH3

Trans-1,2-dimethylcyclopropane

Isomerism in Organic Molecules

Optical isomerism is shown by an organic
compound which has a chiral carbon atom in
its molecules
A chiral carbon atom is a carbon atom which
has four different atoms or groups of atoms
attached to it.
A chiral carbon also known as an
asymmetric carbon, the molecule would
have
a
mirror
image
that
cannot
superimposed on it. A chiral molecule and
its mirror image are called enantiomer

Isomerism in Organic Molecules

Optical isomerism
CH3

CH3

C C H
2 5
H
OH

C2H5 C H
HO
I
I
I
I
I
I
I
I

Introduction to Organic
Molecules Reactions
Covalent bond cleavage during reaction,
chemical bonds have to be broken in order
that new compounds may be formed
Breaking the chemical bonds is called
fission
Bond breaking or formation can be
symmetrical or unsymetrical
Symmetrical bond breaking homolytic
fission
Unsymmetrical bond breaking heterolytic
fission

Introduction to Organic
Molecules Reactions
Homolytic fission two shared electrons of
the covalent bonds are split equally.
The resulting species are known as free
radical
..
A

A. +

.B

Heterolytic fission two shared electrons of

the covalent bonds are remain one one of
the atom
The resulting species known as carbonium
ion
A.

.B

A+ +

.. B-

Introduction to Organic
Molecules Reactions
Carbonium ions there are two species
carbocation and carbanion
Carbocation is an organic ion which contain
a carbon atom with a positive charge
H
H C Cl
H

Methyl chloride

H
H C+

Cl-

Methyl carbocation

Carbanion is an organic ion which contain a

carbon atom with a negative charge
H

H C H

H C- .. +

Methane

Methyl carbanion

H+

Introduction to Organic
Molecules Reactions
Curved arrows - indicate breaking and
forming of bonds
Arrowheads with a half head (fish-hook)
indicate homolytic and homogenic steps
(called radical processes)
Arrowheads with a complete head indicate
heterolytic and heterogenic steps (called
polar processes)

Introduction to Organic
Molecules Reactions
Nucleophile (Nu-) - is a species (ion or
molecule) which attacks electron-poor
carbon atom of organic molecule, by
donating electron-pair to the atom.
Nucleophiles are Lewis bases, containing
lone pair of electrons
Examples: CN-, OH-, Br-, I-, OCH3-, H2O, NH3,
CH3NH2,

Introduction to Organic
Molecules Reactions
Electrophile (E+) -is a species (ion or
molecule) which attacks electron-rich site of
organic molecules such as double bonds.
Electrophiles are Lewis acids (either positive
ions or molecules with electron-deficient
atom)
Examples: HCl , H3O+, AlCl3, BF3, Cl2,
Br2,FeCl3, ZnCl2

Introduction to Organic
Molecules Reactions
Mechanism - describes the steps behind the
changes that we can observe
Reactions occur in defined steps that lead from
reactant to product
We classify the types of steps in a sequence
A step involves either the formation or breaking
of a covalent bond
Steps can occur in individually or in
combination with other steps
When several steps occur at the same time they
are said to be concerted

Introduction to Organic
Molecules Reactions
Main types of reactions
Addition Electrophile or Nucleophile
reactions
Elimination reactions
Substitution Nucleophilic Substitution
Rearrangement reaction

Introduction to Organic
Molecules Reactions
Addition Electrophile or Nucleophile
reactions two reactants added together to
form a single product
X
C C

+ X Y

Y
C C

C O

Nu-

C OH
Nu

Electrophilic addition

Nucleophilic addition

Elimination reactions single reactant splits

into two products X
Y
C C

C C

+ X Y

Introduction to Organic
Molecules Reactions
Substitution or Nucleophilic substitution
reactions two molecules/atoms exchange
parts
Y
Nu
C C

+ Nu-

C C

+ Y

Rearrangement reactions a molecule

undergoes changes in the way its atoms are
connected
C C C C

C C C C

Checkpoint 1
Circle the
functional groups
present in this
molecule

H5C6

C6H5 O

N
H

O
H3C
H3C

O
CH3

O
CH3 OH

CH3

OH
HO
H5C6
O
C
O

O
O

O
CH3

Checkpoint 2
Draw the skeletal structure for each of the
following compound
CH3
CH
H3C

H
C

OH

C
C

CH

H
C

C
H

H
H
H

C
N

OH

C
C

H
H

H
H

Checkpoint 3
1. Draw all chain isomers with a molecular
formula C7H16
2. Draw the functional groups isomer for the
following compounds
a) CH3CH2CH2CH=CH2
b) CH3CH2COOH
3. Draw the positional isomer for the following
compounds
a) CH3CH(OH)CH2CH2CH3
b) 1,2- Diethylcyclohexane

Checkpoint 4
1. Draw the stereoisomer for the following
compounds
a) CH3CH2CBr=CHCH3 and
b) 1,4 Dichloropentane
2. Which of the following compounds exhibit
the optical active? Draw the diagram to
show the optical isomer that may exist for
the particular compound.
a) (CH3)2C(NH2)(COOH)
b) CH3BrCHOH