DK024

Introduction To Organic
Chemistry
1.1 Introduction To Organic Chemistry
Learning Outcomes:

At the end of the lesson the students should be able to :

1.1 Introduction To Organic Chemistry
a) Identify the elements that made up organic
compounds : C,H,O, N, P, S and halogen
**Give structures of organic compounds such as
methane, glucose, urea, DDT, penicillin,nicotine,
caffeine and DNA.
 WHAT IS ORGANIC CHEMISTRY?

Organic chemistry is the chemistry of carbon

compounds.
Organic compounds contain H as well as C, while
other common elements are O, N, the halogens, S
and P.
There are many varieties of organic compounds
( more than 10 millions!!!)
They may exist as simple or complex molecules; as
gases, liquids or solid and coloured or colourless.
 Examples :-

CH4
methane
(natural gas) urea
glucose

Cl CH Cl
CCl3

dichlorodiphenyltrichloroetane
(DDT- a pesticide component)
 O

CH2 NH S
C
N
O
penicillin (an antibiotic) COOH
 1.2 Structural Formula
Learning Outcomes:
At the end of the lesson the students should
be able to :
Define structural formula.
Draw possible structural formulae based on
molecular formula in the form of condensed,
expanded and skeletal structures.
Classify carbons into primary (1°), secondary
(2°), tertiary (3°) and quaternary (4°) carbon.
Classify hydrogens into primary (1°), secondary
(2°) and tertiary (3°) hydrogen.
 STRUCTURAL FORMULA

Structural formula shows how the atoms in a

molecule are bonded to each other.

3 types of structural formula:

a) condensed structure
b) expanded structure
c) skeletal structure
 2- Dimensional formula
a) Condensed Structure

Does not show single bonds between carbon and

hydrogen atoms, but double and triple bonds are
shown.
All atoms that are attached to a carbon are written
immediately after that carbon.
Examples:

i) butane, C4H10 ii) Cyclohexane, C6H12 iii) Aldehyde, CH3CHO

H2
CH3CH2CH2CH3 H2C
C O
CH2 CH3CH
H2C
CH2
C
H2
b) Expanded Structure

Expanded structures indicate how atoms are attached to

each other but are not representations of the actual
shapes of the molecules.

Examples:
haloalkanes, C4H9Cl alcohol, C2H6O acid, C3H6O2
H H H H H H H H O
H C C C C H H C C O H H C C C O H
H Cl H H H H H H
c) Skeletal Structure

Shows only the carbon skeleton.

Hydrogen atoms are not written.
Other atoms such as O, Cl, N etc. are shown.

i) CH3CH(Cl)CH2CH3 =
(condensed structure) Cl
(skeletal structure)

ii) H2C CH2 =

H2C CH2
(condensed structure) (skeletal structure)
 Comparison structural formula of compounds
Structural/ Expanded Condensed Structure Skeletal
compounds Structure Structure
Butane, C4H10 H H H H
H C C C C H
H3C CH2CH2CH3
H H H H

H H H H
Butanol, H3C CH2CH2CH3(OH)
H C C C C OH OH
C4H9OH H H H H

H H H H
Butene, C4H8
H C C C C H H2C CH CH2 CH3
H H

H
Cyclobutane, H H CH2
H
C
H H2C CH2
C4H8 C C
H C C H
H H
CH2 CH2
H

H
Toulene, C7H9 CH
H C CH3 HC C(CH3)
C C
C C HC CH
H C H CH
H
Exercise 3:

Draw expanded structure

a) CH3CH2CH2CH2CH3

b) CH2CH2CH2CH2CH2CH3

Br
c) CH3CH2(OH)CH2CH2CH2 NH2
CH2
e) H2C CH2 CH(CH3)2

H2C CH
CH2
Classification of C atoms:

A carbon atom can be classified as

primary carbon(1o) → bonded to 1 C

secondary carbon(2o) → bonded to 2 C
tertiary carbon(3o) → bonded to 3 C
quarternary carbon(4o) →bonded to 4 C
 Classification of H atoms:
A Hydrogen atom can be classified as

primary hydrogen(1o) →bonded to 1o C

secondary hydrogen (2o) → bonded to 2o C
tertiary hydrogen (3o) → bonded to 3o C

Depending on the type of carbon atom bonded to

it.
There is no quaternary hydrogen.
 10 Hydrogen

H C H

CH3
10 carbon
10 carbon
 10 carbon 10 hydrogen
10 carbon
30 hydrogen CH3

H C CH3

30 carbon CH3
10 hydrogen

10 carbon
Determine the class of C and H atom for the structure below

2 1 1
1 1 1
H H CH3 CH3
1 2 3 2 4 1 1
H C C C CH2 C CH3
2
1
H H H CH3
3 1
Exercise 1:
Count how many C 10, C 20, C 30, C 40, H 10, H 20, and H 30
for the structure below

CH3 H CH2CH3 CH3

CH3 C C C C CH2 CH3

CH2CH3 H H CH2

CH2

CH3
Exercise 1: 7 6 1 2 21 12 1
Count how many C 10, C 20, C 30, C 40, H 10, H 20, and H 30
for the structure below 10 H
10 H 20 H 10 C 10 C
10 C 20 H
CH3 H CH2CH3 CH3
20 C 10 H
10 C 40 C 20 C 20 C 10 C
CH3 C C C C CH2 CH3
10 H 30 C 40 C
20 H 10 H
10 C 20 H
20 C CH2CH3 H H 20 C CH2 20 H
20 H 10 H 30 H
20 C CH2 20 H

CH3
10 C 10 H
Exercise 2:
Count how many C 10, C 20, C 30, C 40, H 10, H 20, and H 30
for the structure below

CH2

H2 C CH2 CH3

H2 C CH CH
CH CH3

H3 C C CH2CH2OH

CH3
Example

Expanded Condensed Skeletal

Structure Structure Structure

CH3(CH2)CCl(CH3)2

H H CH3
H
C C CH
H H CH3
 1.3 Classification Of Organic Compounds
Learning Outcomes:
At the end of the lesson the students should be able to :
• Define functional group.
• Name functional groups
• Classify organic compounds according to their functional
groups. **Differentiate between functional groups and
class of compound.(e.g: alkenes with cycloalkanes,
alcohols with ethers, aldehydes with ketones and carboxylic
acids with esters. )
Define homologous series and explain
general characteristics of its members.
i) represented by a general formula
ii) same functional group and chemical
properties
iii) gradual change in physical properties
with increasing number of carbons
atoms
iv) successive member of a series differs
by a –CH2- unit
State the ability of carbon to form 4
covalent bonds with others carbons or other
elements.
i) single bond
ii) double bond
iii) triple bond
 Functional group
is an atom or group of atoms in an organic molecule
which characterised the molecule and enables it to
react in specific ways which determines its chemical
properties.
Functional groups are important for three reasons:

i. A basic by which organic compounds are divided into

different classes.
ii. A basic for naming organic compounds.
iii. A particular functional group will always undergo similar
types of chemical reactions.
 Classification of organic compound

Functional Group
Class of Example
Compound
Structure Name
Alkane CH3-CH3

carbon-carbon
Alkene -C=C- double bond CH3CH=CH2

carbon-carbon
Alkyne -C C- triple bond CH3C CCH3
Aromatic Benzene ring -CH3
or aromatic
ring

Haloalkane X (F, Cl, Br, I) Halogen CH3Cl

Alcohol -OH Hydroxyl CH3-OH

Phenol -OH Hydroxyl -OH

Ether -C-O-C- Alkoxy CH3-O-CH3

 -C=O CH3-C=O
Aldehyde H Carbonyl H

R-C=O CH3-C=O
Ketone R Carbonyl CH3

Carboxylic -C=O CH3-C=O

acid OH Carboxyl OH

-C-O-C- CH3-C=O
Ester O Carboalkoxy OCH3

-C=O CH3-C=O
Acyl chloride Cl Acyl halide Cl
 O O O O
Anhydride -C-O-C- Anhydride CH3C-O-CCH3

Amide -C=O Carboxamide CH3-C=O

N- NH2

Amine -NH2 Amino CH3-NH2

Nitrile -C N Cyano group CH3C N

Exercises:

1. Identify the functional group in the following

molecules
a) (CH3)3CCH2CH=CH2
b) (CH3)3CCH=CHCH2-OH
c) O O O
C OH C O C CH3

CH3 CH2 OH CH2 O

CH3 C C C CH C NH2

NH2 CH C O CH3
CH2 O
Past-Year : Jun 1999

1. Structural formula of compound for screening the

skin from the sunlight is given as follows:

O
CH3 O CH CH C
O CH2 (CH2)3CH3

Draw and name 3 of the functional groups in the above

structure.
Past- Year Question

Circle and name the functional groups in the following

compound:

CH2CH2OH
O

CHO

H2NH2C
Past- Year Question

Identify the functional groups in the following

structures. Write and name the class of the compounds.

O H
C O
H H H H
HN C C N C C OH
H H H H3C C O

OCH3

OH
 Homologous Series
is series of compounds where each member differs from
the next member by a constant – CH2 unit
Members of the same homologous series are called
homologs.
 Homologs Features
1. Obey a general formula:
Examples:
• Alkane: CnH2n+2
• Alkene: CnH2n
• Alcohol : CnH2n+1OH

2. Differ from the successive homolog by a -CH2 unit

3. Show a gradual change in the physical properties

4. Have same functional group

5. Have similar chemical properties
6. Can be prepared by similar general methods
 Example:
Homologeous series of alkane
Example;
CH4 methane For alkane series,
CH3CH3 ethane C1-C4 gas phase,

CH3CH2CH3 propane C5-C17 liquid phase

C18-onward solid phase
CH3CH2CH2CH3 butane
CH3CH2CH2CH2CH3 pentane
All organic compounds consist of carbon atom.
Properties of carbon atom:
- has 4 valence electrons.
- thus, each carbon atom can form 4 covalent bonds.

C C C C C C

Single bond Double bond Triple bond

 1.4 Hydrocarbons
Learning Outcomes:

At the end of the lesson the students should be able to :

Define hydrocarbons
Classify hydrocarbons into:
i) aliphatic and aromatic; and
ii) saturated and unsaturated
Differentiate between saturated and unsaturated
organic compounds
*include examples for(c)
 Hydrocarbons

saturated unsaturated

Contains only single

bonds ( -C-C- ) Contains at least one
carbon-carbon double
Examples: alkanes, bond (-C=C-) or triple
cycloalkanes bond (-C C-).
Examples: alkenes,
alkynes.
 1.5 Isomerism
Learning Outcomes:

At the end of the lesson the students should be able to :

Classify and draw the constitutional isomers
i) chain isomers
ii) positional isomers
iii) functional group isomers
 is the existence of
Isomerism different compounds
with the same molecular
are isomers with the same molecular formula
formula but differ in the order of
attachment of atoms.

Stereoisomerism
Structural/Constitutional Isomerism

are isomers with the same molecular

formula and the same connectivity but
different arrangement of atoms in space

Chain Positional Functional Group diastreomer enantiomer

Isomerism Isomerism Isomerism

cis-trans other
isomerism diastereomers
 Isomerism
is the existence of different compounds with the same
molecular formula
Different compounds with the same molecular formula
are called isomers.
1) Constitutional isomers (Structural isomers)
 Isomers: molecules with the same molecular formula
but differ in the order of attachment of atoms
Isomerism resulting from different order of attachment
of atoms.

• Three types
a) Chain/skeletal isomerism
b) Positional isomerism
c) Functional group isomerism
a) Chain/skeletal isomerism
The isomers differ in the carbon skeleton
(different carbon chain).
They possess the same functional group and
belong to the same homologous series.

Example:

C5H12
CH3CH2CH2CH2CH3 CH3
CH3CHCH2CH3 CH3CCH3
CH3 CH3
2)Positional isomerism
These isomers have the same carbon skeleton and
belong to the same homologous series, but differ in
the position of functional group

Examples
• C3H7Cl

CH3CH2CH2Cl CH3CHCH3
1-chloropropane
Cl
2-chloropropane
 C4H8 CH2=CHCH2CH3 CH3CH=CHCH3
1-butene 2-butene
C8H10

CH3
CH3 CH3
CH3

CH3 CH3
1,2-dimethylbenzene
1,3-dimethylbenzene
1,4-dimethylbenzene
3)Functional group isomerism

These isomers have different functional groups and

belong to different homologous series with the
same general formula.
Different classes of compounds that exhibit
functional group isomerism :-
General formula Classes of compounds

CnH2n+2O ; n > 1 alcohol and ether

CnH2nO ; n ≥ 3 aldehyde and ketone
CnH2nO2 ; n ≥ 2 carboxylic acid and ester
CnH2n ; n ≥ 3 alkene and cycloalkane
 Examples
C2H6O CH3CH2OH CH3OCH3
ethanol dimethyl ether

C3H6O O O

H3C C CH3 H3C CH2 CH

propanone propanal

C3H6O2 O O

H3C C O
H3C CH2 C OH
CH3
propanoic acid methyl ethanoate
Exercise 1:

1. State how many are isomers with the following

molecular formula, identify the type of isomerism and
draw the structural formula of the isomers.
a) C5H10
b) C5H10O2
Jan 2000

Draw all isomers for C6H14 molecule.

 ANS :

CH3CH2CH2CH2CH2CH3 C H3C HC H2C H2C H3

C H3

C H3 C H3
CH3

C H3C HC H2C H2C H3 C H3C HC HC H3 C H3C C H2C H3

2
C H3 C H3
C H3
 1.6 Basic Reactions In Organic Compounds
Learning Outcomes:
At the end of the lesson the students should
be able to :
Describe covalent bond cleavage:
i) Homolytic cleavage
ii) Heterolytic cleavage
Differentiate between homolytic cleavage and heterolytic cleavage
Define free radical and carbocation.
State the stability of free radicals and carbocation.
State the type of organic reactions:
i) Substitution
ii) Addition
iii) Elimination
 Types of Covalent Bond Cleavage/Fission

All chemical reactions involved bond breaking and

bond making.

Two types of covalent bond cleavage :-

Homolytic cleavage
Heterolytic cleavage
 Homolytic Cleavage
 Occurs in a non-polar bond involving two atoms of
similar electronegativity.
 A single bond breaks symmetrically into two equal
parts, leaving each atom with one unpaired electron.
 Formed free radicals.

Bond breaking
Example :

X :X uv
X + X X X
free radicals
 Heterolytic Cleavage

 Occurs in a polar bond involving unequal

sharing of electron pair between two atoms of
different electronegativities.

 A single bond breaks unsymmetrically.

 Both the bonding electrons are transferred to

the more electronegative atom.

 Formed cation and anion.

 A :- + B+
anion cation
A: B A is more
electronegative

A+ + B :-
cation anion

B is more
electronegative
 The comparison between Homolytic
Cleavage and Heterolytic Cleavage

Homolytic cleavage Heterolytic cleavage

Occurs in a non-polar bond Occurs in a polar bond involving
involving two atoms of similar unequal sharing of electron pair
electronegativity between two atoms of different
electronegativities.

A single bond breaks A single bond breaks

symmetrically into two equal unsymmetrically, both the
parts, leaving each atom with one bonding electrons are transferred
unpaired electron to the more electronegative atom

Form free radicals. Form cation and anion.

 Reaction Intermediates

Carbocation Free Radical

They are unstable and highly reactive.

 Carbocation
 Also called carbonium ion.
 A very reactive species with a positive charge on a
carbon atom.
 Carbocation is formed in heterolytic cleavage.

 Example :
 
(CH3)3C — Cl (CH3)3C+ + Cl-
carbocation anion

 Chlorine is more electronegative than carbon and the

C—Cl bond is polar.
 The C—Cl bond breaks heterolitically and both the
bonding electrons are transferred to chlorine atom to
form anion and carbocation.
 Free Radical
 A very reactive species with an
unpaired electron.
 Formed in homolytic cleavage.
Relative Stabilities of Carbocations,
and Free Radicals

Carbocationand free radical can be

classified into:

 Primary (10)
 Secondary (20)
 Tertiary (30)
 Carbocation Stability
Alkyl group (-R)
example : -CH3

 The alkyl groups (electron releasing group or electron

donating group, EDG) stabilise the positive charge on
the carbocation. (inductive effect)
 The stability of carbocation increases with the number
of alkyl groups present.
 Carbocation Stability

H H R R

<
<
<
H C H < H C < R < H C <R < R C < R
+ + + +
Methyl Primary Secondary Tertiary
carbocation 10 20 30

The stability of carbocation increases

with the number of alkyl groups present
 Free-radical Stability
 The stability of free radical increases as more
alkyl groups are attached to the carbon atom
with unpaired electron.

H H R R
H C
. H < H C
. R < H C
. R <R C
. R
methyl Primary Secondary Tertiary
radical 10 20 30

The stability of free radicals increases

with the number of alkyl groups present
Exercises :
1. Explain how the free radicals are formed in
homolytic cleavage.

2. Write an equation for the bromine-bromine

bond cleavage in the bromination of methane.
State the type of bond cleavage.
3. Which would you expect to be the most
stable free radical ?
CH2CH3 , (CH3)2 CH , CH3
 4 Types of Organic Reactions
1. Addition a) **Electrophilic Addition
b) **Nucleophilic Addition

2. Substitution a) **Free radical substitution

b) **Electrophilic substitution
c) **Nucleophilic substitution
3. Elimination
1. Addition Reaction
A reaction in which atoms or groups add to
adjacent atoms of a multiple bond.
Initiated by an electrophile or a nucloephile
Typical reaction of unsaturated compounds such as
alkenes and alkynes.
Example :
CH2Cl2
CH3CH=CH2 + Br2 CH3CHBrCH2Br
Room
temperature
O HO
H3C + HCN H3C CH3
CH3 CN
2) Substitution Reaction
 A reaction in which an atom or group in a
molecule is replaced by another atom or group.
Example :
 Substitution with free radical
Cl2
H3C CH3 H3C CH2Cl
uv

 Substitution with nucleophile

OH- -
H3C CH2Cl H3C CH2OH + Br
 Substitution with electrophile
Br
Br2
+ HBr
FeBr3
 Elimination Reaction

 An atoms or groups are removed from adjacent

carbon atoms of a molecule to form a multiple
bond (double or triple bond).
 Results in the formation of unsaturated
molecules.
 Example :

conc. H2SO4
CH3CH2OH CH2= CH2 + H2O
Δ