Introduction to Organic

Chemistry
1.1 Chemistry of carbon
1.2 Types of organic compound
1.3 Applications of organic compound
 At the end of this chapter, you
should be able to:
1) understand the concept of organic compound.
2) understand the properties of organic compound.
3) understand the application of organic
compound.
4) classify the organic compound.
5) write the formula of organic compound.
6) recognise the types of organic reactions
 Definition
• Organic chemistry – a branch of chemistry that
studies carbon compounds.
• History
– Organic chemistry was first defined as a branch of
modern science in the early 1800's by Jon Jacob
Berzelius. He classified chemical compounds into
two main groups:
• Organic: if they originated in living or once-
living matter
• Inorganic: if they came from "mineral" or non-
living matter.
 Natural vs synthethic organic
compounds
Names Origin Usage
Natural Proteins Animals 1. As structural material
(enzymes, 2. As biological catalyst
hormones) and regulators
Fats and oils Animal/Vegetables Store energy
(triglyceride)
Vitamins (A,B Food Growth and functioning
etc)
Synthetic Plastics Poly-, perspex Packaging, plastic bags
Medicines/ Tranquilizer etc Treat illness
drugs
Pesticides DDT Kills houseflies etc
Dyes Methylene blue Give colour to material
Organic vs inorganic compound
 Properties of typical organic vs
inorganic compound
Inorganic
Property Organic compound
compound
Bonding with
Usually covalent Often ionic
molecule
Forces between Generally weak Quite strong
molecules (Intermolecular force) (Electrostatic force)
Normal physical Gases, liquids or low- Usually high-melting-
state melting-point solids point solids
Usually
Flammability Often flammable
nonflammable
Solubility in water Insoluble Soluble
Conductivity Nonconductor Conductor
Rate of chemical
Slow and complex Fast and simple
reaction
 Carbon (cont.)
• Group 14
• Electron configuration ns2 np2
• Importance of carbon:
– Basis for all living things
– Can form stable covalent bond to other carbon
atoms [catenation]

Ability to form long chain of bonds with itself

• Question – why there are no life form of
silicon although it is similar to Carbon?
Carbon
 Type of organic compound
Linear

Cyclic
Aliphatic
Saturated
Organic
Aromatic
compound
Unsaturated
Alicylic
 TYPES OF ORGANIC COMPOUNDS
Aliphatic
● OPEN chains of carbon atoms.
● Unbranched or Branched
● Contain Single, Double or Triple bonds.
Example: ethane (CH3–CH3)
ethene / ethylene (CH2=CH2)
ethyne / acetylene ( HC CH )
H
Aromatic H H
● CLOSE rings of carbon atoms.
● Contain a benzene ring. H H
Example: Benzene H
Alicyclic C C
● CLOSE rings of carbon atoms.
● Rings form the shape of POLYGON (triangle, square,
O
rectangle or etc).
Example: Epoxide
Saturated
Compound that contains only single bond.
Example: alkane
H H

H C C H ethane

H H
Unsaturated
Compound that contains multiple bond.
Example: alkene, alkyne H H
HC CH C C ethene
ethyne
H H
Aliphatic hydrocarbon (cont.)
Formula of organic compound
Molecular

Empirical
5 types
Structural

Condensed

Bond line
Type Definition Example
Molecular formula Actual number of atoms of C6H12O6
each element in a molecule
Empirical formula Simplest ratio of number of CH2O
atoms of each elements in a
molecule
Structural Bonds are represented in lines
and show all the atoms in the
molecule

Condensed A system or writing organic Propane

structure in a single line of CH3CH2CH3
text.
Bond line Represent structure by
showing bonds between
carbons and atoms other than
hydrogen. Atoms other than C
and H are called heteroatoms.
 Formula of organic compound
(cont.)
Type Ethane Pentane
Molecular C2H6 C2H15
Empirical CH3 -
Structural

Condensed CH3CH3 CH3(CH2)3CH3 or

CH3CH2CH2CH2CH3
Bond
 Functional groups
• Definition – an atom/group of atoms which
determine the chemical and physical
properties of an organic compound
• Importance
– Units used to divide the organic compounds into
classes
– Served as basis on naming any organic compounds
– Sites of chemical reaction : each functional group
undergoes the same reaction in whatever
compound it is found
 Functional groups (cont.)
• Classifying organic compounds by functional
group -
– Hydrocarbons C and H only
– Alcohols R - OH
– Acids R - COOH
– Amines R – NH2
– Ketones R (C=O)R’
– Aldehydes R - CHO
 Homologous series
• Definition – series of compounds where each member
differs from the next member by a constant –CH2
• All the member of a particular homologous series have:
1. Same general formula eg : CnH2n+1OH
2. Same functional group : same chemical reactions. Eg:
all alcohols contain –OH group.
3. Each member differs from the next member by a
constant –CH2.
4. As the molecular size increase, the boiling points
increase.
Name of Series General chemical formula*

Alkanes CnH2n+2
Alkenes CnH2n
Alkynes CnH2n-2
1-bromoalkanes CnH2n+1Br
(e.g. of Haloalkanes)
1-alcohols CnH2n+1OH
(e.g. of Alcohols) = CnH2n+2O
Aldehydes CnH2nO
Carboxylic Acids CnH2nO2
Acid Chlorides CnH2n-1OCl
Amines CnH2n+1NH2
= CnH2n+3N
Amides CnH2n-1ONH2
= CnH2n+1ON
Nitriles CnH2n-3N
* where n represents the number of carbon atoms in the chain. Note that
in some cases the minimum value of the number of carbons in the chain
(n) is greater than 1 (n>1). For example, ethene (2 carbons) is the
smallest alkene and ethanenitrile (2 carbons) is the smallest nitrile.
Example: Alkane series
 Isomerism
• Definition: A
molecule with the
same molecular
formula but a
different
structural/spatial
arrangement of
atoms
 Structural isomerism
• Definition: Compound with the same number of
atoms and bonds but with different arrangements
 Structural isomerism (cont.)
• Pentane (C5H12)

• Hexane (C6H14)

(CH3CH2)2CHCH3
2-Methylpentane

• 2,3-dimethylbutane (CH3CH2)2CHCH3
• 2,2 - dimethylbutane 3-Methylpentane
 Stereo isomerism
• Definition – compound with the same molecular
formula and structural formula but with different
arrangement of their bond in space.
 Chemical bonding
• Definition : Lasting attraction between atoms that
enables the formation of chemical compounds
• May result from:
– Electrostatic force of attraction between atoms of opposite
charges
– Sharing of electrons
• Types:
– Ionic
– Covalent
– Polar
– Hydrogen
 Chemical bonding (cont.)
• Ionic bond : Atoms can neither transfer or share their valence
electrons

• Covalent bond : Involve sharing of a pair of electron valence

between 2 atoms
 Chemical bonding (cont.)
• Polar bond : When a molecule have different
electronegativities value between the atoms.

• Hydrogen bond : a weak bond between two molecules

resulting from an electrostatic attraction between a proton in
one molecule and an electronegative atom in the other.
 Type of organic reactions

General

Addition Substitution Elimination Rearrangement

Specific

Hydrogenation Esterification Oxidation Hydrolysis

 Mechanism terms
• Electrophile: a Lewis acid; attracted to the electron
density found in a chemical bond or lone pair.
Electron-loving reagent.

• Nucleophile: a Lewis base; attracted to the + charge of

a nucleus or cation. Nucleus-loving reagent

• Free radicals: molecules or ions with unpaired

electrons and hence generally extremely reactive.
 General organic reactions
• Addition
– Alkene and alkyne undergoes addition to break
double/triple bond
– Two substances react together to form a single substance

• Substitution
– An atom/group (leaving group) in a molecule is replaced
by another atom/group (nucleophile/electrophile)
 General organic reactions (cont.)
• Elimination
– Removal of atoms or groups of atoms from a saturated
molecule to form an unsaturated molecule

• Re-arrangement
– Migration of an atom, a group of atoms or a bond from
one atom to another within molecule to form its isomer.
 Specific organic reactions (cont.)
• Hydrogenation
– Addition of hydrogen to a mulriple bond to form a single
bond substances

• Esterification
– Acid – catalyzed ester formation between alcohol and
carboxylic acid
 Specific organic reactions (cont.)
• Oxidation
– An increase/decrease in the number of bonds between
carbon and oxygen

• Hydrolysis
– A chemical process where a molecule is split into two
parts by the addition of water molecule
 Applications
• Biology and biochemistry
• Petroleum
• Polymers
• Generic engineering
• Agriculture
• Pharmacology
• Consumer products