INTRODUCTION TO

ORGANIC CHEMISTRY
 TOPICS
1.1 Introduction to Organic Chemistry
1.2 Alkanes and Cycloalkanes
1.3 Alkenes and Alkynes
1.4 Aromatic Compounds
1.5 Alkyl Halides
1.6 Alcohols
1.7 Aldehydes and Ketones
1.8 Carboxylic Acids and their Derivatives
1.9 Amines

2
 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 bonds
- 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

7
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

8
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

9
 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 H H
Formula I : Ethanamine Formula II : Dimethylamine
H H H H H H
H C C C O H H C O C C H
H H H H H H
Formula I :1-Propanol 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 H H H H
H C C C O H H C C C H C C C C H
H H H H 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 CH3CH CH(CH2)2CH3
H H H H
 Ways of Depicting the Organic
Molecules
• Skeletal structural formula – shows the
carbon skeleton, the atom hydrogen omitted
on carbon, unless hydrogen bound to the
heteroatoms. H H O O

H C C C O H OH
H H OH OH H H
C H H H H H
H C
C
H C H H C C C C H
C
H H H H
H
H H H H
H C C C N H
NH2
H H H
 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 dash represent a group
Cl going behind of the plane
of paper
Cl 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 – one atom 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 molecule‟s 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

Functional Example
Class
Group
CH3

Alkene C C

H3C CH2
Limonene
1.1 Introduction to Organic Chemistry
Functional Groups
Functional
Class Example
Group H
OH C
CH3 C

Alkyne C C

O Norethindrone
1.1 Introduction to Organic Chemistry
Functional Groups
Functional Example
Class
Group
Cl
Cl Cl
R X
Alkyl Halide
X = F, Cl, Br, I
Cl Cl
Cl
1,2,3,4,5,6-Hexachlorocyclohexane
Lindane
1.1 Introduction to Organic Chemistry
Functional Groups
Functional Example
Class
Group
CH3

Alcohol R OH
OH

H3C CH3
2-Isopropyl-5-methylcyclohexanol
Menthol
1.1 Introduction to Organic Chemistry
Functional Groups
Functional
Class Example
Group
HO (CH2)4CH3

H3C
Ether R O R'
O

H3C CH3
9
 -Tetrahydrocannabinol
THC
1.1 Introduction to Organic Chemistry
Functional Groups
Functional Example
Class
Group
H O
O C C
Aldehyde C H
C
R H H
Cinnamaldehyde
1.1 Introduction to Organic Chemistry
Functional Groups
Functional Example
Class
Group
CH3
O
O
Ketone C
R R'
CH3
Jasmone
1.1 Introduction to Organic Chemistry
Functional Groups
Functional
Class Example
Group
CH3
O OH
Carboxylic CH3 C
Acid C
R OH O
CH3
Ibuprofen
1.1 Introduction to Organic Chemistry
Functional Groups
Functional Example
Class
Group
O
O C CH3
Ester C R' O
R O
OH
Methyl salicylate
1.1 Introduction to Organic Chemistry
Functional Groups
Functional Example
Class
Group

H3CO NH2

N
Amine R R"
R' 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
O O
C C
H3CH2C H 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 –CH2-
group 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 General Example Structural
series Formula Formula
Alkanes CnH2n+2 C6H14 CH3(CH2)4CH3
Alkenes CnH2 C6H12 CH3(CH2)3CH=CH2
Alkynes CnH2n-2 C3H4 CH3CCH
Haloalkanes CnH2n+1X C3H7 Br CH3CH2CH2Br
Alcohols CnH2n+2 O C3H7 OH CH3CH2CH2OH
Aldehydes CnH2n O C4H8 O CH3CH2CH2CH=O
Ketones CnH2n O C 4 H8 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
Stereoisomerism
Isomerism

Chain Positional Functional Geometrical Optical

Isomerism Isomerism Isomerism Isomerism 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 H C H
H C C C C H H H
H H H H H C C C H
n-butane H H H
(Unbranched) Isobutane
(Branched chain)
See page 77 - 81
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 2-Bromobutane

See page 77 - 81
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 H H
Propanal Propanone

See page 77 - 81
Isomerism in Organic Molecules
 Possible structural isomers of alkanes
Carbon Molecular Formula Possible
Chains Isomers
4 C4H10 2
5 C5H12 3
6 C6H14 5
7 C7H16 9
8 C8H18 18
9 C9H20 35
10 C10H22 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 CH3
C C C C
H H H3C H
Cis-2- butene Trans-2- butene

H3C CH3 H3C H

H H
H H H CH3
H H
Cis-1,2-dimethylcyclopropane 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 C 2H 5 C H
H 2 5
OH 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 B A. + .B

• Heterolytic fission – two shared electrons of

the covalent bonds are remain one one of
the atoms
• 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
H C Cl H C+ + Cl-
H H
Methyl chloride Methyl carbocation

• Carbanion is an organic ion which contain a

carbon atom with a negative charge
H H
H C H H C- .. + H+
H H
Methane Methyl carbanion
 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 Y
C C + X 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 O
present in this
C
molecule H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
Amide H OH
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH Ester
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
Ketone
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH Ether
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
Alcohol
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
HO
H5C6 O O
Alkene C O

O C
O CH3
 Answer

O
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
HO
H5C6 O O
C O

O C
O CH3
 Answer

O
Ester
C
H3C O
O C6H5 O H3C O
CH3 OH
C C CH3
H5C6 N O
CH3
H OH
HO
H5C6 O O
C O

O C
O CH3
 Checkpoint 2
Draw the skeletal structure for each of the
following compound
H
H
CH3 H
C OH
H C H H C C
CH C N
C C
H3C CH H H
C C
C C C
OH
H N H 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