FUNDAMENTALS OF

ORGANIC CHEMISTRY
PST 11205
FST11205
ESNRM11205
 PST 11205

Subject

Credits
Course
semester

Year
 Prerequisites
• Advanced level Chemistry

3
 Evaluation
-Quizzes (daily )
-Assignments
-Mid-semester Examination 20 %
-Final examination 60 %
80% attendance

4
References

5
Chemistry as a central science
 Chemistry related jobs
• Government sector
• Research Institutes
• tea, coconut, rubber, medical, sugar cane, agriculture, veterinary, textile , nanotechnology
• Sri Lanka scientific service –ministry of public administration
• Government Analyst’s department (government analyst)
• Medical research institute (research officer)
• Hospitals (Biochemist)
• Food Laboratory (Chemist) –Ministry of Health
• Department of irrigation
• Railway
• Colombo municipal council
• Ministry of Science and Technology
• Sri Lanka Standard institution (SLS) chemist, directors
• Industrial technology institute –Research officer, directors
• Academic Institutions: Schools, Universities, technical colleges etc
• Sri lanka Customs
• Sri Lanka Pharmaceutical manufacturing cooperation
• Ceylon petroleum cooperation
• National drugs control board
• Water board
 Chemistry related jobs
• Private sector
• Pharmaceutical industry
• Natural products
• Food and beverages industry
• Paint industry
• Agrochemical industry
• Polymer industry
• Water
• Laboratory chemicals , instruments
• Medical equipment
• Education
International exposure
• BSC –final year
• MSC/MPhil local or international;
• PhD international USA, EU , Japan, Canada, China, New Zealand,
Australia, Singapore, etc
• You can be a member of international research team
Organic Chemistry PST/FST/ESNRM 11205
• Course Content –Part I
• Introduction
• Electronic structure and bonding of C, lewis structures
• Hybridization
• Electronegativity, Dipole moment
• Intermolecular forces
• Solubility of organic compounds
• Acid-base properties of organic compounds
• Hyperconjugation , inductive effect and resonance
Organic Chemistry PST/FST/ESNRM 11205
• Course Content –Part II
• Isomerism
• Conformational analysis of Cyclic alkanes
• IUPAC nomenclature of organic compounds
• Introduction to organic reactions and their mechanisms
 Organic chemistry
• Organic chemistry is the study of the structure, properties, composition,
reactions, and preparation of carbon-containing compounds

1s2, 2s22p2
Atomic orbitals
Chemical Bonding
Chemical Bonds
• Chemical bonds are the attractive forces that hold atoms together in
the form of compounds
• There are 3 types of bonds...
• covalent bonds,
• polar covalent bonds
• ionic bonds
Covalent bond
• A covalent bond is formed when there is an equal sharing of
electrons between two atoms. The atoms forming a covalent bond
must have relatively equal attraction for the electrons.
Polar covalent bond
• If the atoms differ in their attraction for electrons, a polar-covalent
bond will be formed
• The attraction of electrons to the nucleus of an atom is a very
important property of atoms and is called electronegativity. The
difference in electronegativity between bonded atoms determines the
bond polarity.
Ionic Bonds
• An ionic bond is formed when an electron is essentially transferred
from one atom (of a pair) to the other creating ions.
• The ions are held together by electrostatic attractions. Ionic
compounds have high melting points and many are soluble in water.
 Hybridization
Methane (CH4),
• The three 2p orbitals of the carbon atom are combined with its 2s
orbital to form four new orbitals called "sp3" hybrid orbitals.
• These new orbitals will have an energy slightly above the 2s orbital
and below the 2p orbitals
These hybrid orbitals have 75% p-character and 25% s-

 
character which gives them a shape that is shorter and fatter
than a p-orbital.
                                                  

    
C2H4,
• ethene, both carbon atoms will be sp2 hybridized and
have one unpaired electron in a non-hybridized p
orbital.
• These p-orbitals will undergo parallel overlap and form one pi bond
Ethyne H2C2 (acetylene).
• Both carbon atoms will be sp hybridized and have one
electron in each of two unhybridized p orbitals.
• Unhybridized p orbitals will undergo parallel overlap to form two pi-
bonds at right angles to each other.
•
Commonly use notations
Alkyl group Structure origin Notation for Alkyl
group

Methyl H
H (Methane)
Me
H C H C H

H H

Ethyl H H
H H
(Ethane)
Et
H C C H
H C C

H H H H

H
Propyl H H (Propane)
Pr
H3C C C H3C C CH3
H H H

Butyl Bu

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Commonly use notations
• Normal propyl n-Pr
• Iso propyl iso-Pr
• Iso butyl iso-Bu
• Tertiary butyl t-Bu
• Neo pentyl neo-Pe

• EtOH, MeOH, n-PrOH, t BuBr

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Fundamentals
Bond lysis

• Homolysis

A B A˙ + B˙
• Heterolysis Free radicals

A B A+ + B‾
ions

Note: Carefully observe the shapes of arrows

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Main types of reagents

• Nucleophiles:- Electron rich reagents

- - -
OH, OEt, SEt, H2O:, H3N:
• Electrophiles:- Electron deficient reagents
+ +
H , NO2, AlCl3, O3
• Free radicals

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Structural effects
How does the structure effect on the reaction
- -
R Br + OH R OH + Br

R = CH3 R = CH3 CH2

H 3C Br Me CH2 Br

Relative Rate 1 0.08

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Structural effects

(1) Electronic effects

Inductive effect - Two types
 Electron donation (+I)
 Electron withdrawal (-I)

(2) Steric effects

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 Structural effects
Structural effects

Electronic effects Steric effects

Inductive effect

Electron donation (+ I) Electron withdrawal (  I)

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Electronic effects

• Inductive effect
Electron donation (+I)
    
Me CH2 Br H3C Br 

Methyl group will decrease the positive polarization of –CH2 group

(by donating electrons)
-
OH attack is somewhat more difficult

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Electronic effects

Electron withdrawal (-I)

H
   O 2N C CH 2 Br
H3C Br 
H

NO2 is an electron withdrawing group

∴-CH2 group is now more liable to
nucleophilic attack

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Fundamentals
Free radicals
H H
H C H C + H˙
H H
H

Primary radical
H H
H C H C + H˙
H CH3
CH3

CH3 CH3
H3C C H + H˙ Secondary radical
C
H3C H
H

CH3 CH3
+ H˙
Tertiary radical
H3C C H C
H3C CH3
CH3

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Fundamentals
• Stability of free radicals- free radicals are very
reactive (unstable)
• Stability can be described by
Hyperconjugation
• More hyperconjugation more stable

H
H
H C H
H C H
C
C H3C CH3
H3C CH3

Note: Carefully observe the shapes of arrows 35

Hyperconjugation

• How many hyperconjugation structures can you

draw?
H

H C H Nine (9) structures

C
H3C CH3

H
C
H H Here we cant draw any hyperconjugation structure

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Hyperconjugation

H
H

H C H H C
H
Six(6) structures can be drawn
C C
H CH3 H CH3

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Hyperconjugation

Free radical No of hyperconjugation

structures
H Primary
0
C
H H

H Primary
03
C
H3C H

H Secondary 06
C
H3C CH3

CH3 Tertiary 09
C
H3C CH3
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