Organic Chem

Introduction to
Organic Chemistry
1
1 New Way Chemistry for Hong Kong A-Level Book 3A
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What is Organic
Chemistry?
3 New Way Chemistry for Hong Kong A-Level

3 New Way Chemistry for Hong 3A
Kong A-Level Book 3A
21.1 What is Organic Chemistry (SB p.2)
Organic Chemistry
• Chemistry of the compounds present

in living organisms.
• They all contain carbon.
• Organic Chemistry is the Chemistry
of Carbon.

Natural Sources of Organic Compounds

Living Carbohydrates /
things Proteins / Fats /
Vitamins /
Antibiotics
A variety of
organic products
obtained from
living things
Natural Sources of Organic Compounds
Fractional distillation / Alkanes /

destructive distillation Alkenes /
Crude oil
Alkynes /
or coal
Aromatic
hydrocarbons
A variety of
useful products
derived from
crude oil and coal
Development of Organic Chemistry

as a Science
In the past
…,
Chemistry
Chemistry
Organic
Organic Inorganic
Inorganic
compounds
compounds compounds
compounds
obtained from obtained from
living organisms non-living sources

as a Science
In 1828, Wohler (a German chemist)
(Inorganic (Organic
compound) compound)

as a Science
Redefining … ...
Organic chemistry
Organic chemistry is is the
the study
study ofof carbon
carbon
compounds (except
compounds (except CO,
CO, CO
CO22,, carbonates,
carbonates,
hydrogencarbonates, carbides
hydrogencarbonates, carbides and
and
cyanides) obtained
cyanides) obtained from
from natural
natural sources
sources or
or
synthesized in
synthesized in the
the laboratories.
laboratories.

The Unique
Nature of Carbon

What are living things made of?

I’m made of what???
Guess how many elements your body is made up of?
• 25 elements make up all living thing
About 97%
of your
body’s mass is made of
just 4 elements:
oxygen, carbon,
hydrogen, & nitrogen.
Two other major

elements are
phosphorous & sulfur.

The most important element is…
Carbon
If you take away the water, the rest of the human body is
53% carbon.
It may not be the most abundant element in living things,
but it certainly is the most important.
The carbon molecules were so complex, scientists

thought they must have been made in some unknown
way. They called these carbon compounds
ORGANIC compounds
Why do carbon compounds
outnumber all other compounds so
dramatically?
The answer lies in carbon’s atomic

structure and behavior.

Diamond Graphite
21.2 The Unique Nature of Carbon (SB p.5)
1)Carbon is TETRAVALENT
and can form 4 bonds by sharing
electrons i.e covalent bonds
• Electronic configuration of carbon

(ground state) : 1s22s22p2
Carbon (ground state)

• Each carbon atom has four unpaired

electrons when excited
Carbon (excited state)
• Tend to form four strong covalent bonds

2. Ability to Catenate
• Carbon atoms link together to form

chains of varying length, branched
chains and rings of different size
Catenation- the tendency of atoms of an element to

unite with each other forming a chain of covalent
bonds is known as
CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3

3. Ability to Form Multiple Bonds

sp3
4 bonds
sp2
1 bond, 3 bonds
sp
2 bonds, 2 bonds
Carbon (excited state)

Single bond Double bond Triple bond
* X = halogens

3 Types of Carbon Backbones

4. THE DIVERSITY OF CARBON
Because of catenation and branching:
MILLIONS of organic compounds are known

The great diversity of carbon compounds makes
carbon a natural element on which to base
complicated LIVING SYSTEMS
"Imagination is more important

than knowledge" - Albert Einstein

Organic Chemistry
Molecular Orbitals
and Hybridisation

Atomic Orbitals
Heisenberg Uncertainty Principle states that :
it is impossible to define what time and where an
electron is and where is it going next.
• a series of calculations are used to approximate

the volume and time in which the electron can
be located.
• these regions are called Atomic Orbitals.
These are also known as the quantum states of the electrons.

Hybridization of Atomic Orbitals
Atomic orbitals for each atom combine to

form new atomic orbitals - hybrid
orbitals, (overlapping with orbitals from
other atoms.)
Hybrid orbitals are formed by

combinations of atomic orbitals by a
process called hybridization.

Molecular orbitals
Orbitals can be used to explain bonding between
atoms.
H H
1s atomic orbitals of hydrogen
The atomic orbitals containing the valence electrons

(outer electrons) are the ones that are important to us.
When atomic orbitals overlap, they combine to form
molecular orbitals.
In the case of hydrogen, the overlap of two 1s atomic

orbitals results in the formation of a σ (sigma)
molecular orbital.
H H H H
σ molecular
1s atomic orbitalsorbital
of hydrogen
σ bonds
This are covalent
molecular orbital bonds
is moreformed
stablebetween
than eachatoms
of the
when end-on
separate overlap
atomic of orbitals
orbitals occurs. to the shape
and contributes
of the molecule.
Types of bonds
+
s-s
+
s-p
+
p-p
sigma bond forms due to end-to-end or head-

on overlap

Types of bonds
+ or
This is formed by lateral or sideways overlap which is

possible for p or d-orbitals.
Sigma bond is stronger than pi bond due to greater

extent of overlap.

Difference between sigma and pi
bonds
Formed by head-on Formed by side ways
overlapping of s-s or s-p overlapping of unhybridised
or p-p or any hybrid p-orbital
orbital
First bond between any Rest are 

two atoms is always sigma bonds
In plane of Perpendicular to plane of

molecule molecule
Stronger as compared to Weaker as compared to bond

bond
Hybridization of 1 s and 3 p
Orbitals – sp3

In Ground State
2 bonding sites, 1 lone pair
H
CH4 2p
C x y z
H 2s
H ground state
H

sp Hybridization
3
4 Regions of electron Density

H
CH4 2p
C x y z
H 2s
H ground state
H
hybridize
2p x y z
2s 4 identical sp3 orbitals
excited state 4 sigma bonds requires 4 hybrid orbitals
tetrahedral geometry
4
sp3
Mix one s + three p’s -> 4 sp3 hybrid orbitals…
energy
+
C
-
- +
-
Orbital Depiction of Ethane,
C2H6 , the  bond

sp Hybridization
2
3 Regions of Electron Density

CH2=CH2
H H 2p x y z
C C 2s
ground state
H H
hybridize pz
2p x y z
3 identical sp2 orbitals
2s
trigonal planar geometry
3
sp2 pz
Hybridization of 1 s and 2 p
Orbitals – sp 2

An sp2 Hybridized Atom

Ethylene CH2=CH2

sp Hybridization
2 Regions of Electron Density
H C C H 2p x y z
2s
ground state
hybridize py pz
2p x y z
2 identical sp orbitals
2s
linear geometry

Mix one 2s + one 2p orbitals  two sp hybrid orbitals;
two 2p orbitals “left over”  two -bonds
energy
120 pm

Acetylene, C2H2,
1 bond
2 perpendicular  bonds

σ and π bonds
Looking at information comparing σ and π bonds, we
can see that double bonds are stronger than single
bonds, but not twice as strong. This is because the
sideways overlap (π bond) is weaker than the end-on
overlap (σ bond).
Bond type Bond Bond length Mean

present bond enthalpy
C C single 154 pm 370 kJ mol–1
C C double 134 pm 602 kJ mol–1
C C triple 121 pm 835 kJ mol–1

Hybrid orbitals

Organic Chem

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Introduction to

2 New Way Chemistry for Hong Kong A-Level Book 3A

3 New Way Chemistry for Hong Kong A-Level

• Chemistry of the compounds present

4 New Way Chemistry for Hong Kong A-Level

Natural Sources of Organic Compounds

Natural Sources of Organic Compounds

Fractional distillation / Alkanes /

Development of Organic Chemistry

Development of Organic Chemistry

Development of Organic Chemistry

9 New Way Chemistry for Hong Kong A-Level

10 New Way Chemistry for Hong Kong A-Level

11 New Way Chemistry for Hong Kong A-Level Book 3A

Two other major

12 New Way Chemistry for Hong Kong A-Level Book 3A

The carbon molecules were so complex, scientists

The answer lies in carbon’s atomic

14 New Way Chemistry for Hong Kong A-Level Book 3A

• Electronic configuration of carbon

Carbon (ground state)

• Each carbon atom has four unpaired

Carbon (excited state)

• Tend to form four strong covalent bonds

17 New Way Chemistry for Hong Kong A-Level

• Carbon atoms link together to form

Catenation- the tendency of atoms of an element to

18 New Way Chemistry for Hong Kong A-Level

3. Ability to Form Multiple Bonds

Carbon (excited state)

Single bond Double bond Triple bond

22 New Way Chemistry for Hong Kong A-Level

23 New Way Chemistry for Hong Kong A-Level Book 3A

MILLIONS of organic compounds are known

"Imagination is more important

24 New Way Chemistry for Hong Kong A-Level Book 3A

25 New Way Chemistry for Hong Kong A-Level Book 3A

• a series of calculations are used to approximate

• these regions are called Atomic Orbitals.

These are also known as the quantum states of the electrons.

26 New Way Chemistry for Hong Kong A-Level Book 3A

Atomic orbitals for each atom combine to

Hybrid orbitals are formed by

27 New Way Chemistry for Hong Kong A-Level Book 3A

1s atomic orbitals of hydrogen

The atomic orbitals containing the valence electrons

In the case of hydrogen, the overlap of two 1s atomic

sigma bond forms due to end-to-end or head-

30 New Way Chemistry for Hong Kong A-Level Book 3A

This is formed by lateral or sideways overlap which is

Sigma bond is stronger than pi bond due to greater

31 New Way Chemistry for Hong Kong A-Level Book 3A

First bond between any Rest are 

In plane of Perpendicular to plane of

Stronger as compared to Weaker as compared to bond

33 New Way Chemistry for Hong Kong A-Level Book 3A

34 New Way Chemistry for Hong Kong A-Level Book 3A

4 Regions of electron Density

38 New Way Chemistry for Hong Kong A-Level Book 3A

3 Regions of Electron Density

40 New Way Chemistry for Hong Kong A-Level Book 3A

41 New Way Chemistry for Hong Kong A-Level Book 3A

42 New Way Chemistry for Hong Kong A-Level Book 3A