ORGANIC

CHEMISTRY 1
CHM456
Carbon Compounds and Chemical Bonds Course Outline
1.1 Structure of carbon compounds
1.2 Chemical bonds: ionic and covalent bonds
1.3 Polar and nonpolar molecules: Formal charge and resonance
1.4 Intermolecular forces
1.5 Hybridization, Atomic and Molecular orbitals

Introduction to Organic Reactions

2.1 Reactions and mechanisms: substitution, elimination, addition and
rearrangement
2.2 Homolysis and heterolysis of covalent bonds, homogenic and heterogenic of
bonds
2.3 Acid-base reactions:
2.2.1 Carbocations and carbanions
2.2.2 Strengths of acids and bases: Ka and pKa
2.2.3 Structure and acidity: resonance and inductive effects

Stereochemistry
3.1 Isomerism:
3.1.1 Structural and geometric isomers: position, functional groups, E and Z
3.1.2 Optical isomers: chirality, racemic mixture,meso compound, specific
rotation
3.2 Molecules with more than one stereocenter

Alkanes and cycloalkanes

4.1 Structure and Nomenclature
4.2 Physical Properties
4.3 Bond Rotation and Conformational Analysis of Butane
4.4 Stability of Cycloalkanes: Ring Strain and Conformation of Cyclohexane
4.5 Synthesis of Alkanes: Hydrogenation of Alkenes and Alkynes, Reduction of
Alkyl Halide, Alkylation of terminal Alkynes
4.6 Reaction of Alkanes with Halogens: Chlorination of Methane
Alkyl Halides
Course Outline
5.1 Structure and Physical Properties of Alkyl Halides
5.2 Nucleophilic Substitution Reactions
5.2.1 Nucleophiles and Leaving Groups
5.2.2 SN2 Reaction: Kinetics, Mechanism and Stereochemistry
5.2.3 SN1 Reaction: Mechanism, Carbocations and Stereochemistry
5.2.4 Factors affecting SN2 and SN1 Reactions
5.3 Elimination Reactions of Alkyl Halides
5.3.1 E2 Reactions
5.3.2 E1 Reactions
5.4 Substitution versus Elimination

Alkenes and Alkynes

6.1 Alkenes: Nomenclature, Structure and Physical Properties
6.2 Reactions and Mechanisms
6.2.1 Synthesis of Alkenes via Elimination Reactions: Dehydrohalogenation,
Dehydration, Debromination
6.2.2 Addition Reactions : and Markovnikov’s and AntiMarkovnikov’s Rule
6.3 Alkynes: Nomenclature, Structure and Physical Properties
6.4 Reactions and Mechanisms
6.4.1 Addition, Hydration, Oxidation and Reduction

Alcohols and Ethers

7.1 Structure, Nomenclature and Physical Properties

7.2 Synthesis of Alcohols from Alkenes
7.3 Reactions of Alcohols, Alcohols as Acids; Conversion to Alkyl Halides; Oxidation
to Carbonyl Compounds
7.4 Synthesis and Reactions of Ethers
7.5 Phenols: Structure and Nomenclature; Synthesis and Reactions

Benzene and Aromaticity

8.1 Introduction: Benzene, Nomenclature; Structure and Stability; Huckel’s Rule

8.2 Other Aromatic Compounds and Heterocyclic Aromatic Compounds
8.3 Reactions of Aromatic Compounds
8.3.1 Electrophilic Aromatic Substitution
8.3.2 Halogenation; Nitration and Sulfonation
8.3.3 Friedel-Craft’s Alkylation and Acylation
Teaching Methodology

Lectures and laboratory sessions

Assessment

Assignments : 10%
Tests : 30%
Laboratory reports : 20%
Final examination : 40%

Recommended Text

Solomons and Fryhle. 9th Edition. Organic Chemistry.

Wiley 2007
Morrison Boyd. Organic Chemistry
McMurray, J. Organic Chemistry
What is Organic Chemistry?
 Organic Chemistry in Your Life
•Food
–Fertilizer, pesticides,
preservatives, additives

•Materials
–Polymers, coatings,
adhesives…
•Drugs
–Aspirin, Viagra, Neurofen…

•The entire modern world

–Petrochemicals, environmental chemistry, etc…
The magic Carbon atom
• Difference between organic and
inorganic is C-atom ability to
form very long chain
(catenation)
– Inorganic compound will become
unstable after with 12 or more
atoms.
– C-atoms ability to form very strong
covalent bond
 CHAPTER ONE
Structure and Bonding
 Chapter 1 - Structure and Bonding

ELECTRON CONFIGURATION

Electrons reside around the nucleus in discrete energy levels. These energy
shells contain orbitals - a mathematical probability that an electron will
exist in that space. Orbitals are described by quantum mechanics in distinct
shapes. S orbitals are spherical and p orbitals are shaped like dumbbells.

Aufbau Principle - the lowest energy orbital fills up first

Pauli Exclusion Principle - only two electrons can occupy an orbital and they
must be of opposite
Spin

Hund’s Rule - if two or more orbitals of equal energy are available they are
filled with one electron of parallel spin until all are half filled. Only then will
electrons be paired up. This is important in filling the three p orbitals

Valence electrons are those in the outermost energy shell of an atom.

 Chapter 1 - Bonding and Structure

Ionic Bonds - Atoms held together by electrostatic attraction (ions).

Covalent Bonds - Atoms share electrons between them - much stronger than ionic
bonds.

Carbon (1s22s22p2) would have to gain or lose 4 electrons to achieve a filled shell and is
therefore not easily ionized. Carbon forms covalent bonds rather than ionic bonds.

Molecule - a collection of atoms held together by covalent bonds.

Lewis Structures - represent the valence electrons around the atom by dots. Covalent
bonds are shown with the two electron ‘dots” shared between the atoms.

Kekulé Structures - Each covalent bond is represented by a single line indicating two
shared electrons.
Chapter 1 - Bonding and Structure
 Chapter 1 - Bonding and Structure

Three-Dimensional Formulas
Chapter 1 - Bonding and Structure
 Chapter 1 - Bonding and Structure
RESONANCE

Resonance stabilization is most important when it serves to delocalize a charge

over two or more atoms : e.g. carbonate
 Chapter 1 - Bonding and Structure
HYBRIDZATION

THE STRUCTURE OF METHANE AND ETHANE: sp3 HYBRIDZATION

Orbital hybridization: A mathematical approach that involves the

combining of individual wave functions for s and p orbitals to obtain wave
functions for new orbitals ⇒ hybrid atomic orbitals
Chapter 1 - Bonding and Structure
HYBRIDZATION
 Chapter 1 - Bonding and Structure
HYBRIDZATION-METHANE
Formation of a C–H bond The shape of an sp3 orbital
 Chapter 1 - Bonding and Structure
HYBRIDZATION-ETHANE
Formation of a C–H bond The shape of an sp3 orbital
 Chapter 1 - Bonding and Structure
HYBRIDZATION- THE STRUCTURE OF ETHENE (ETHYLENE):
sp2 HYBRIDZATION

A process for obtaining sp2-hybridized carbon atoms

 Chapter 1 - Bonding and Structure
HYBRIDZATION- THE STRUCTURE OF ETHENE (ETHYLENE):
sp2 HYBRIDZATION
 Chapter 1 - Bonding and Structure
HYBRIDZATION- THE STRUCTURE OF ETHENE (ETHYLENE):sp2
HYBRIDZATION
 Chapter 1 - Bonding and Structure
HYBRIDZATION- THE STRUCTURE OF ALKYNES (ACETYLENE):
sp HYBRIDZATION

A process for obtaining sp-hybridized carbon atoms

Chapter 1 - Bonding and Structure
 Chapter 1 – Polarization-Intermolecular Forces

• Polarization is a change in electron distribution as a response to change in

electronic nature of the surroundings
• Polarizability is the tendency to undergo polarization
• Polar reactions occur between regions of high electron density and regions of low
electron density