CHM258

CHAPTER 1
 LESSON OUTCOMES
In the end of this chapter, student should be able to :
1. Explain the characteristic features of organic compounds.
2. Write the chemical formula using full structural formula, condensed structural
formula and skeletal formula.
3. Define organic chemistry terms: hydrocarbon, isomers, electrophiles, nucleophiles,
Lewis base or acid.
4. Differentiate the isomerism type such as structural isomerism, geometrical
isomerism and optical isomerism.
5. Identify the functional group and homologous series.
6. Physical properties : solubility and boiling point.
 LESSON OUTLINES
Introduction
1.1 Characteristics features of organic compounds
 Valance Bond Theory
 Chemical formula: Molecular formula and structural formula
1.2 Definition: Hydrocarbon, Isomer, Electrophiles, Nucleophiles, Lewis acids and Lewis bases
1.3 Isomerism
 Structural isomerism, Geometrical isomerism and Optical isomerism
1.4 Homologous series
1.5 Physical properties
 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
 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
 EXAMPLE

Sigma bond (σ) Pi bond (π)

 2 atomic orbital overlap  2 p orbital overlap
 End to end overlap  Side by side overlap
CHEMICAL FORMULA
Chemical
formula

General Structural
formula formula

Molecular Empirical
Expanded Condensed Skeletal
formula formula
I) 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

Simplest ratio number of
Actual number of atoms of
atoms of each element in a
each element in a molecule.
molecule.
- C6H12O6
- CH2O
II) STRUCTURAL FORMULA

Structural
formula

Expanded Condensed Skeletal

A) EXPANDED STRUCTURE
Shows every atom and type of covalent bond in the molecule.

Ethane But-2-ene
Ethanol
B) CONDENSED STRUCTURE
Eg:
C-C &C-H : CH3CH(CH3)CH2CH3
branches in the CH2(OH)CH2CH3
not shown carbon chain are
C=C or CΞC : are indicated in
shown. parentheses.

each central if have two or

Eg: atom is shown more identical
CH3CH2CH3 together with groups use
the atoms that Eg: parentheses and
CH2=CHCH3
are bonded to it. CH3(CH2)4CH3 a subscript.
CH3CH2CH2OH
C) 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 2-methyl hexane

CH3CH2CH2CH2CH2CH3 CH3CH2(CH3)CH2CH2CH2CH3
1.2 DEFINITION OF TERMS

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 covalent bond
1.3 ISOMERISM
I) STRUCTURAL ISOMERS
II) GEOMETRICAL ISOMER
(DIASTREOISOMERISM)
Cis-isomer has the
same atom or
group on the same
side

Trans-isomer has
the same atom or
group on the
opposite side.
 III) 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.
EXAMPLE
EXAMPLE
EXAMPLE
 1.5 PHYSICAL PROPERTIES

Solubility Boiling Point

→ insoluble in water Increase if
→ soluble in non-polar →high carbon number
solvent →Less branch
 1. 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).
II) BOILING POINT
– Physical states (at room temperature)
 C1 - C4 : gases
 C5 - C18 : liquids
 > C18 : solids
 II) BOILING POINT
1. Effect of molecular mass on boiling point
– 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
 II) BOILING POINT
2. 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