CHM257

CHAPTER ONE
INTRODUCTION TO
ORGANIC CHEMISTRY
DR. NAZRIZAWATI AHMAD TAJUDDIN
PhD United Kingdom
 LESSON OUTLINES
1. Introduction
1.1 Characteristics features of organic compounds
 1.1.1Valence bond theory
 1.1.2 Chemical formula: Molecular formula and structural formula
1.2 Definition: Hydrocarbon, isomers, electrophiles, nucleophiles, Lewis acid dan Lewis bases
1.3 Isomerism
 1.3.1 Structural Isomerism
 1.3.2 Geometrical Isomerism
 1.3.3 Optical Isomerism
1.4 Homologous series
1.5 Physical properties of Organic Compounds
 1.5.1 Solubility
 1.5.2 Boiling point
 LESSON OUTCOMES

At the end of this chapter, student should be able to :

1. Explain the characteristic features of organic compound: Valence Bond
theory and able to write chemical formula.
2. Define organic chemistry terms such as hydrocarbons, isomers,
electrophiles, nucleophiles, Lewis base or acid.
3. Differentiate the isomerism type such as structural isomerism, geometrical
isomerism and optical isomerism.
4. Identify the homologous series in organic chemistry families such as
alkanes, alkenes, alkynes, cyclic hydrocarbons, aromatic hydrocarbons.
5. Know the physical properties of organic compounds :solubility and boiling
point
What is Organic Chemistry

 Activity: Run & Write down anything you know is belong to Organic
Chemistry –at the whiteboard!
 The branch of chemistry that deals with carbon compounds (other than
simple salts such as carbonates, oxides, and carbides).
 https://www.youtube.com/watch?v=Jnof5NmYlZU
 What is organic plants?
 https://www.youtube.com/watch?v=BebNsezt6r0
 1. INTRODUCTION

 Organic chemistry is the study of CARBON-containing compounds in living

organisms and non-living organisms.
 Other elements which is commonly presented in organic substances are
hydrogen (H), oxygen (O), halogens (Cl, Br, F) & nitrogen (N).
 Over 10 million of organic compounds have been identified.
 Animals, plants & other form of life consists of organic compounds –
nucleic acids, proteins, fats, carbohydrates, enzymes, vitamins &
hormones.
 Source:
✓ Living : Carbohydrates, collagen, fats, proteins, vitamins
✓ Non-Living : Crudes oil or coal
1.1 CHARACTERISTIC FEATURES OF
ORGANIC COMPOUNDS
Ability to
catenate
- Stable
bonding
Form four Form multiple
covalent bond
bond - single, double
- 1s22s22p2 & triple

CARBON
 ❑ 1.1.1 Valence Bond Theories

✓ A stable arrangement using only valence (outer) electrons.

✓ Through bonding, atoms attain a complete outer shell configuration which is like a noble
gas (octet or duplet).
✓ Polarity of a bond depends upon the electronegativity and size of the atoms forming the
bond.

Covalent Ionic
• Sharing of electrons • Transfer of electrons
between two from one element
elements. to another.
➢ Valence Bond Theory

 A covalent bonds forms when two atoms approach each other closely and a
singly occupied orbital on one atom overlaps a singly occupied orbital on the
other atom.
 The electrons are now paired in the overlapping orbitals and are attracted to the
nuclei of both atoms and bonding the atoms together.
 Example: H2 molecule
 Continue…

Sigma bond (σ) Pi bond (π)

➢ 2 atomic orbital overlap ➢ 2 p orbital overlap
➢ End to end overlap ➢ Side by side overlap
❑ 1.1.2 Chemical Formula

Chemical
formula

General Structural
formula formula

Molecular Empirical Fisher

Expanded Condensed Skeletal
formula formula projection
➢ General formula

 Represent the members in homologous series.

✓ Example: Alkanes: CnH2n+2, n=no. of carbon atoms
 Two types : molecular and empirical formula

Molecular formula Empirical formula

EXAMPLE : - Actual number of - Simplest ratio number
GLUCOSE atoms of each element of atoms of each
in a molecule. element in a molecule.
- C6H12O6 - CH2O
➢ Structural formula

Structural
formula

Fisher
Expanded Condensed Skeletal
projection
➢ Expanded structure

 Shows every atom and type of covalent bond in the molecule.

 Example:

Ethane: But-2-ene: Ethanol:

 ➢ Condensed structure

Eg:
CH3CH(CH3)CH2CH3
C-C &C-H : branches in CH2(OH)CH2CH3
the carbon
not shown
chain are
C=C or CΞC : indicated in
are shown. parentheses.
each central if have two or
atom is shown more identical
together with groups use
Eg: the atoms that Eg: parentheses
CH3CH2CH3 are bonded to CH3(CH2)4CH3
and a
CH2=CHCH3 it.
CH3CH2CH2OH
subscript
➢ Skeletal structure

 Do not show carbon and hydrogen atoms or C-H bonds unless they are
part of a functional group.
 single bonds are indicated with a single line, double bonds with double
lines and triple bonds with triple lines.
 the ends of the lines and corners between lines indicate the presence of a
carbon atom.

Hexane: CH3CH2CH2CH2CH2CH3 2-methyl hexane: CH3CH2(CH3)CH2CH2CH2CH3

➢ Fisher Projection

 3D representation uses a line to represent a bond on the plane of paper.

✓ Wedge : bond coming out
✓ Dash : bond pointing to the back

=
 1.2 DEFINITIONS

Hydrocarbon Isomer Electrophiles

Nucleophiles Lewis Acid Lewis Base

➢ Hydrocarbon and Isomer

 Hydrocarbon
❑ any compound that contain carbon and
hydrogen only
 Isomer
❑ compound that have same molecular formula
but different arrangement of atom
 ➢ Electrophiles Vs. Nucleophiles
Electrophiles
• Substance that is electron-loving or
electron seeking
• Electron poor atom and can form a
bond by accepting a pair of
electrons from nucleophiles
• Either neutral or positively charged
• Usually Lewis Acids
Nucleophiles
• Substance that is nucleus-loving or
nucleus seeking
• Electron rich atom and can form a
bond by donating a pair of
electrons to an electrophiles
• Either neutral or negatively charged
• Usually is a Lewis base
Example…
 ➢ Lewis Acid Vs. Lewis Base

 Lewis acid: any species that accepts an electron pair to form a covalent bond.
 Lewis base: any species that donates an electron pair to form a new covalent bond.
1.3 ISOMERISM
❑ 1.3.1 STRUCTURAL ISOMERS
➢ 1.3.2 GEOMETRICAL ISOMER /
DIASTREOISOMERISM

 Form cis-trans isomers. Cis-isomer has the

same atom or
group on the
same side.

Trans-isomer has
the same atom or
group on the
opposite side.
➢ 1.3.3 OPTICAL ISOMER/ ENANTIOMERS

 A pair of stereoisomers with structure that are mirror images of each other but
non superimposable.
 Observed in molecules with one or more chiral carbons.
 **chiral carbons : carbon that has four different atoms or groups bonded to it.

Max. no of stereoisomers is 2n,

n : is the number of chiral carbon
Example…
Exercise

 Identify the chiral carbon in below structure;

Answer
 1.4 HOMOLOGOUS SERIES

 Functional Group
✓ Atoms, group of atoms or bond that determine the chemical
properties of organic compounds.

 Homologous Series
✓ Group of compounds with the same functional groups.
✓ Member of homologous series are called homologs.
✓ Homologs have similar chemical properties & may be prepared by
similar chemical methods.
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 1.5 PHYSICAL PROPERTIES

Solubility Boiling Point

→ insoluble in water Increase if
→ soluble in non-polar →high carbon number
solvent →Less branch
➢ SOLUBILITY

 Soluble in non-polar solvents such as benzene and weak non-polar

organic solvents such as dimethyl ether (CH3-O-CH3).
 Insoluble in water:
✓ hydrocarbon are non-polar and do not form hydrogen bonds
with water molecules.
✓ described as ‘hydrophobic’ (water hating).
➢ BOILING POINT

 Physical states (at room temperature)

✓ C1 until C4 : gases
✓ C5 until C18 : liquids
✓ above C18 : solids
 Boiling points of straight chain alkanes increase steadily with
relative molecular mass
✓ due to increasing forces of attraction between molecules.
 * A larger molecule, with greater surface area and greater van
der Waals attractions, boils at higher temperature *
CONTINUE…

→ Effect of branching on boiling point

 Hydrocarbon with same number of carbon:

✓ Branched chain: lower BP (more volatile)
✓ Straight chain: higher BP

 Reason: The branched chain compound

✓ more compact (nearly spherical),
✓ have smaller surface area,
✓ smaller van der Waals forces of attraction and at lower temperature.
THE END….