Organic Chemistry 2021

1 New Way Chemistry for Hong Kong A-Level Book 3A
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Putting it Together
1) Chemical formula: 2) Atomic sequence:
HNO3
O N O
O
3) Number of bonds =5 H
4) Remaining electrons = 14
5) Lewis Structure with 5 bonds:

6) Complete Lewis Structure
O N O with 14 remaining electrons
O
O N O
H
O
H
Lewis Dot Structure of CO2 by Bonds Table
A. Calculate Octet electrons (Oe-) and B. Calculate the number of bonds in compound
Total Valence electrons to determine structure.
number of bonds # bonds = (Oe - TVe)
2
CO2 Oe TVe
1C 1•(8)= 81•(4) = 4 = (24- 16) = 8 = 4 bonds
2 2
2O 2•(8)=162•(6)=12
C. Calculate the remaining electrons to add to
Chg structure to complete Lewis dot structure.
24 16 Remaining e- = TVe - e- used in bonding.
= 16 - 8 = 8 e-Remaining
Writing Lewis Structure:
First determine atom connectivity keeping in mind that H and F can never be central
atoms. Generally when given the formula, ABn, A is the central atom in the structure
(but not always), and B atoms flank the central atom. Next use information from the
above calculations. Total of 16e- in CO2, of which 8 electrons are used to form 4 bonds
and 8 remaining electrons are used to complete Lewis structure.
O C O O C O O C O
1,2. Write atom 3,4,5. Draw the four 6. Place the remaining 8 electrons in the
connectivity for CO2. bonds in the structure. structure to complete the Lewis Structure
Lewis Dot Structure of ClO4- by Bonds Table
A. Calculate (Oe-) and (TVe) B. Number of Bonds.
ClO4- Oe TVe # bonds = (40- 32) = 8 = 4 bonds

2 2
1 Cl 1•(8)= 81•(7) = 7
C. Remaining electrons.
4O 4•(8)= 32 4•(6)= 24
Remaining e- = 32 - 8 = 24 e-Remaining
Chg 1
40 32
Writing Lewis Structure:

6. Place the remaining 24 electrons
1,2. Write atom 3.4.5. Draw the
in the structure such that each atom
connectivity for ClO4-. four bonds in the
has an octet to complete the Lewis
structure.
Structure
O O O
O Cl O
O Cl O O Cl O
O
O O
Example
Lewis Structures: Examples
a) CH2ClF Cl b)SO2
H C F O S O
H
2- O
c) SO4 d) H3PO4 O
O S O H O P O H
O O
H
A balloon analogy for the mutual repulsion of electron groups

Electron-group repulsions and the five basic molecular shapes
Ideal bond angles are shown for each shape.

The single molecular shape of the linear
electron-group arrangement
Examples:
CS2, HCN, BeF2

The two molecular shapes of the trigonal planar
Class
Examples: Shape
SO2, O3, PbCl2, SnBr2

Examples:
SO3, BF3, NO3-, CO32-

The three molecular shapes of the tetrahedral
Examples:
CH4, SiCl4,
SO42-, ClO4-
Examples: Examples:
NH3 H2 O
PF3
OF2
ClO3
SCl2
H3O+

Lewis structures and molecular shapes

The four molecular shapes of the trigonal bipyramidal
Examples:
Examples:
SF4
PF5
XeO2F2
AsF5
IF4+
SOF4
Examples:
Examples: IO2F2-
ClF3 XeF2
BrF3 I3 -

IF2-
The three molecular shapes of the octahedral
Examples:
SF6
IOF5
Examples: Examples:
BrF5 XeF4
TeF5- ICl4-
XeOF4

Carbon: Organic Chemistry
• Carbon is an unusual atom in that it is able to
form very strong covalent bonds with other
carbon atoms.
• When we then include it’s ability to also bond
with other elements we open up the possibility
of the highly diverse and complex molecules
(like DNA) that have led to the possibility of life.
• Because of this, the chemistry of carbon
containing compounds is often called organic
chemistry.

Ability to form four strong covalent bonds
• Electronic configuration of carbon

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

Ability to form four strong covalent bonds
• Each carbon atom has four unpaired

electrons when excited
• Tend to form four strong covalent bonds
Carbon (excited state)
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Ability to Catenate
• Carbon atoms link together to form

chains of varying length, branched
chains and rings of different sizes
• Catenation:
è Ability of atoms in forming stable
bonds with itself, hence joining up
into chains or rings
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21.2 The Unique Nature of Carbon (SB p.6)
Single bond Double bond Triple bond
* X = halogens
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What is Organic
Chemistry?
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Development of Organic Chemistry
as a Science
In the past …,
Chemistry
Organic Inorganic
compounds compounds
obtained from obtained from
living organisms non-living sources
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Origin of organic compounds
• Naturally occurring organic compounds are
found in plants, animals, and fossil fuels
• All of these have a plant origin
• All of these rely on the “fixing” of C from CO2
• Synthetic organic compounds are derived
from fossil fuels or plant material

21.1 What is Organic Chemistry (SB p.3)

as a Science
In 1828, Wohler (a German chemist)
(Inorganic (Organic
compound) compound)
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Simple Organic Compounds
• Most compounds that contain the element carbon

are organic compounds made by living organisms
or synthesized in laboratories.
• More than 90 % of carbon compounds are organic.

• Most current research focuses on Organic
• Originally from “organic” meaning life
• Not just chemistry of life, chemistry of carbon
• Exceptions:
– oxides of carbon (CO2, CO)
– carbonates,bicarbonates(NaHCO3,CaCO3)
– cyanides (NaCN, etc)
One C with no H, or with metal C C C

• Carbon can form four bonds…
C C
21.1 What is Organic Chemistry (SB p.3)

as a Science
Redefining … ...
Organic chemistry is the study of carbon

compounds (except CO, CO2, carbonates,
hydrogencarbonates, carbides and cyanides)
obtained from natural sources or
synthesized in the laboratories.
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• I. Objectives: At the end of the session, the
students will be able to:
• a. identify the properties and specific uses of
organic compounds;
• b. write and name the correct formulas of alkanes
and alkenes and
• c. demonstrate appreciation regarding the
properties of alkanes and alkenes by relating to
their structures.
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Natural Sources of Organic Compounds
Living Carbohydrates /
Things Proteins / Fats /
Vitamins /
Antibiotics
A variety of
organic products
obtained from
living things
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Natural Sources of Organic Compounds
Fractional Distillation Alkanes /

Petroleum/ Alkenes /
Alkynes /
Crude oil /
Aromatic
Coal hydrocarbons
A variety of
useful products
derived from
crude oil and coal
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What is Petroleum?
• Petroleum is a dark, flammable liquid often called

crude oil. It exists deep within Earth. Coal, natural
gas, & petroleum are all called fossil fuels because
they come from fossilized material.
• Oil wells pump crude oil to Earth’s surface.
• Engineers separate the mixture by fractional
distillation at refineries in metal towers called
fractionating towers.
Distillation
• Distillation works by evaporating the liquid from

the solution
• Distillation can separate a liquid from a solution
(Example: water from a salt solution)
• It is then cooled and condensed into a separate
container

Boiling Temperature
• Another example: Water and ethanol have different
boiling points - the ethanol will boil first (78oC), and then
the water (100oC) enabling us to separate the two
compoenents
• This is known as fractional distillation

Crude oil is separated into
different chemicals in a
process called fractional
distillation. The crude is
heated to above 350°C and
then allowed to pass through
a large column.
Lighter gases are collected at
the top while heavier liquids
fall further to the bottom. At
different locations, the
fractions are collected and
piped away.
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-It started out as crude oil extracted from the ground,
then shipped to an oil refinery where it is heated to
above 350°C in a pressurized chamber and is
distilled to gasoline.
-Gasoline is the most common automobile fuel used
all over the world to power cars, motorcycles and
other machineries.
-It is made from petroleum and blended with
additives such as ethanol or aromatics to boost its
octane rating to increase engine’s power and
performance.
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-It is commonly available in three octane ratings or
grades. Generally, the lowest octane rating is
considered the cheapest gasoline option.
-Unleaded gasoline literally means that it does not

contain lead. Tetraethyl lead was added to fuel to
reduce the volatility of the gas, increase the octane
rating and improve fuel economy.
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-Like gasoline, diesel fuel undergo a refining
process before use. At the refinery, crude oil is
heated to temperatures between 200-350 C and
distilled into diesel fuel. Many large, industrial
trucks and off-road vehicles use diesel fuel.
-Diesel powered cars typically get better gas
mileage than gasoline powered vehicles and some
drivers feel that they get a better value for their
money. Generally acknowledge as being more
efficient and emits fewer greenhouse gases.
-Biodiesel is created using vegetable oils or animal
fats. It can be made using soybean oil, lard, algae
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and
40 vegetableNewoils.
Way Chemistry for Hong Kong A-Level Book 3A
Activity
Solubility in Water Solubility in Alcohol Type of Compound

(Ionic or Covalent)
1. Salt
2. Sugar
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Comparison of Properties of Organic
and Inorganic Compounds
Property Organic Inorganic
Solubility in inorganic
solvent (water)
Solubility in organic
solvent (alcohol)
Conductivity
Flammability
Volatility
Melting Point
Boiling Point
Comparison of Properties of Organic
and Inorganic Compounds
Property Organic Inorganic
Solubility in inorganic Generally not soluble soluble

solvent (water)
Solubility in organic Generally soluble Not soluble
solvent (alcohol)
Conductivity Non-conductive conductive
Flammability Generally flammable Not flammable
Volatility More volatile Not volatile
Melting Point Low High
Boiling Point Low High

-Phase of matter is the physical state of the material.
-Volatility is the measure of the tendency of
substance to evaporate or to turn into its gaseous
state.
-Flammability is the measure of how easily a
material burns.
-Viscosity is a measure of a fluid’s resistance to
flow.
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Hydrocarbons
• A compound that is made of only carbon and
hydrogen is called a hydrocarbon.
• Natural gas contains the hydrocarbon methane or
CH4.

How can C atoms arrange themselves?
• Carbon atoms can bond
together as chains,
branched chains, &
rings.

Flow Chart
Organic compounds
Straight chains
Contain only C & H are called
Branched chains
hydrocarbons
Cyclic chains
Bond as
Single Double Triple

bonds bonds bonds
Homologous Series
• Members in the same series can be
represented by a general formula.
alkanes: CnH2n+2
alkenes: CnH2n
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Homologous Series
Functional group
Chemical
of an organic
properties
compound
Members of a homologous series

have similar chemical properties
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Homologous Series
• The physical properties change gradually
along the homologous series
• e.g. the longer the carbon chain in the

molecule ( or the greater the
molecular mass)
è the greater the attractive force
between molecules
è the higher the melting point,
boiling point and density
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Alkanes
• The simplest hydrocarbons form a series of
compounds known as alkanes.
• These all consist of carbon and hydrogen only and
every carbon has four single covalent bonds.
Hydrocarbon Formula Structure
Methane CH4
hydrogen
Ethane C2H6 carbon
Propane C3H8
Butane C4H10

Names of Alkanes
• The names of the 4 simplest alkanes are methane,
ethane, propane and butane.
• After that the names are systematic (like the words
used to describe geometric shapes.) E.g.
– 5 carbons = pentane C5H12
– 6 carbons = hexane C6H14
– 7 carbons = heptane C7H16
– 8 carbons = octane C8H18
– 9 carbons = nonane C9H20
– 10 carbons = decane C10H22
hydrogen
pentane
carbon

Homologous Series
• Alkanes all have very similar structures.
• They have a CH3 at each end of the molecule.
• What differs is the number of CH2 groups
between the two ends.
• These all consist of carbon and hydrogen only
and every carbon has four single covalent bonds.
• It is possible to build up a series by simply adding
an extra CH2 group
• This leads to a general formula of CnH2n+2
n= 1 n=2 n=3
n=4
hydrogen
carbon
Activity
• What will be the formula for alkanes

containing the following numbers of
carbons?
Number of carbons Formula
12 C12H26
16 C16H34
31 C31H64
19 C19H40

Formulae and Models of Alkanes
• Although normal chemical formula - like C5H12 -
are used to describe alkanes they do not convey
which atom is joined to which other atom.
• To get around this we often used displayed
formula to describe organic molecules.
• Displayed formula show which 4 atoms each
carbon is bonded to but even these do not show
the actual 3D shapes. For that we use models.
H
methane, CH4 H C H
H
Alkanes
H
H C H methane, CH4
H
H H
H C C H ethane, C2H6
H H
H H H
H C C C H propane, C3H8
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H H NewHWay Chemistry for Hong Kong A-Level Book 3A
butane, C4H10
H H H H
H C C C C H
H H H H
pentane, C5H12
H H H H H
H C C C C C H
H H H H H
hexane, C6H14 H H H H H H
H C C C C C C H
H H H H H H
Notice
the carbon chain
is not really
straight
and so on………
Isomerism
Alkanes of the same formula can have different
arrangements of atoms. Such different arrangments
are known as isomers.
Two isomers of C4H10 are shown
H H H
H H H H H C C C H
H C C C C H H H
H H H H H C H
H
Isomers of
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butane
New Way Chemistry for Hong Kong A-Level Book 3A
Combustion of Alkanes
• Alkanes are not especially reactive but they do
have one very important reaction: combustion.
• With an adequate supply of air they react to
form carbon dioxide and water.
Methane + oxygen ! water + carbon dioxide

CH4 + 2O2 ! 2H2O + CO2

Incomplete Combustion of Alkanes
• In the absence of an adequate

supply of air, alkanes may react
to form carbon monoxide and
water.
• Carbon monoxide is highly
poisonous and this is one
reason why gas boilers must be
serviced regularly. A carbon
monoxide
detector
Methane + oxygen ! water + carbon monoxi

2CH4 + 3O2 ! 4H2O + 2CO
Alkenes
• When carbon forms compounds each carbon
atom always forms four bonds.
• This does not, however, mean that each
carbon is joined to four other atoms.
• It is possible to have bonds grouped into pairs.
These are called double bonds.
• Alkenes contain carbon atoms joined by
double covalent bonds.
C C
Single covalent bond
C C
Double covalent bond

Alkenes - homologous series
• A series of alkanes exist differing only in the
number of CH2 groups.
• The same is true for alkenes.
• This leads to a homologous series with the
general formula Cn H2n
Alkene n= 1 n=2 n=3

sn=4
hydrogen
none = = =
carbon

• What will be the formula for alkenes
containing the following numbers of
carbons?
Number of carbons Formula
11
C11H22
13
C13H26
32
C32H64
21
C21H42

Ethene - formula
• The simplest alkene is ethene.
• It has the formula C2H4
• The carbon atoms are joined together by a
double bond.
• Its displayed formula may be drawn in slightly
different forms but should always clearly show
the double bond.
H H
H H
C C or C C
H H
H H
Ethene – electron structure
• In all alkenes there
are two carbon H H
atoms that are joined
by two pairs of
electrons. C C
• This is the double
bond.
H H
H H
C C
H H

Activity
• Displayed formula for propene and butene are

shown.
• Draw a displayed structure for pentane.
H H H H H H
H H C
C H C H C H
C C H H C H H C H
C C H C C H
H H H H H H

Saturated or Unsaturated?
• Saturated means “filled up”.
• Alkanes are saturated.
• Every carbon atom has already used all four
of it’s bonds to join to four other atoms. No
other atoms can be added.
• Alkenes are unsaturated.
• They have a double bond that could instead

become two single bonds. This means that
other atoms can be added. It is not “filled up”.

• Alkenes are unsaturated and so extra atoms
can be added to alkene molecules.
• This forms the basis of a test to distinguish
between alkanes and alkenes.
• When bromine water is added to an alkane
nothing happens but when bromine is added
to an alkene the red color of the bromine
disappears.
H H Br Br
C C Br2 ! H C C H
+
H H H H
Bromine
loses this
red colour Gas red
colourless
Activity
• Copy the Table and complete the empty boxes.
Number Name Alkane or Formula

of alkene
carbons
5 pentene alkene C5H10
8 octane
alkane C8H18
4 butene
alkene C4H8
10 decane
alkane C10H22

• Write the structural and expanded formulas of
heptane and heptene.
• alkanes: CnH2n+2
• alkenes: CnH2n
• 71
What is Organic Chemistry
(a) How was organic chemistry defined before 1800s?

Answer
(a) The knowledge of organic and inorganic
compounds was raised during the 1780s.
Scientists defined organic chemistry as the
study of compounds that could be obtained
from living organisms. They believed that the
synthesis of organic compounds took place in
living organisms only.
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What is Organic Chemistry
Back
(b) How is organic chemistry defined nowadays?

Answer
(b) Nowadays, scientists have discovered that
many organic compounds can be synthesized
from inorganic substances. The updated
definition of organic chemistry is the study of
carbon compounds, except for carbon
monoxide, carbon dioxide, carbonates,
hydrogencarbonates, carbides and cyanides.
These compounds have been traditionally
classified under inorganic chemistry.
73 New Way Chemistry for Hong Kong A-Level 3A

The Unique Nature of Carbon (SB p.5)
Why is carbon able to catenate?

Answer
The ability to catenate of carbon is chiefly due to
the high strength of the C¾C single bond (bond
enthalpy of C ¾ C single bond is 356 kJ mol-1).
Back

Factors Affecting the Physical Properties of Organic Compounds
Why is oil immiscible with water?

Answer
Oil molecules do not have free ¾OH groups,
so they cannot form hydrogen bonds with
water molecules.
Back

Factors Affecting the Physical Properties of Organic Compounds
The relative molecular mass of glucose is 180.0, but it

is soluble in water. Why?
Answer
Glucose molecules have ¾OH groups, so
they are able to form hydrogen bonds with
water molecules. Therefore, glucose is
soluble in water despite it has a high
molecular mass. Back
76

Organic Chemistry 2021

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

5) Lewis Structure with 5 bonds:

ClO4- Oe TVe # bonds = (40- 32) = 8 = 4 bonds

Writing Lewis Structure:

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

Ideal bond angles are shown for each shape.

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

SO2, O3, PbCl2, SnBr2

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

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

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

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

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

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

• Electronic configuration of carbon

Carbon (ground state)

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

• Each carbon atom has four unpaired

• Tend to form four strong covalent bonds

Carbon (excited state)

• Carbon atoms link together to form

Single bond Double bond Triple bond

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

Development of Organic Chemistry

• Most compounds that contain the element carbon

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

One C with no H, or with metal C C C

Development of Organic Chemistry

Organic chemistry is the study of carbon

Fractional Distillation Alkanes /

• Petroleum is a dark, flammable liquid often called

• Distillation works by evaporating the liquid from

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

• This is known as fractional distillation

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

-Unleaded gasoline literally means that it does not

Solubility in Water Solubility in Alcohol Type of Compound

Solubility in inorganic Generally not soluble soluble

Flammability Generally flammable Not flammable

Volatility More volatile Not volatile

Melting Point Low High

Boiling Point Low High

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

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

Single Double Triple

Members of a homologous series

• e.g. the longer the carbon chain in the

Ethane C2H6 carbon

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

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

• What will be the formula for alkanes

Number of carbons Formula

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

Methane + oxygen ! water + carbon dioxide

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

• In the absence of an adequate

Methane + oxygen ! water + carbon monoxi

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

Alkene n= 1 n=2 n=3

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

Number of carbons Formula

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