ALKANE

ALKENE

ALCOHOL

CARBOXYLIC ACID

ESTER

ALCOHOLS

LEARNING
OUTCOMES :
Students should be able to :
State the general formula of alcohols
Identify the functional group of alcohols
List the names and the molecular formulae of the
first four alcohols
Draw structural formulae for isomers of propanol and
butanol
Name isomers of propanol and butanol using IUPAC
nomenclature
Describe the industrial production of ethanol
Describe the preparation of ethanol in the laboratory

Contain
carbon,
hydrogen
and oxygen

Non hydrocarbons

alcohols

General
formula

Functional
group

C
H

A functional group is a
special group of atoms
attached to an organic
molecule.

Functional Group : hydroxyl group, -OH

General Formula : CnH2n+1OH

NAMING ALCOHOLS

The names of straight chain alcohols can be

derived from alkanes.
Alcohols are named by replacing the ending e
from the name of the alkane with ol.

NAMING
ALCOHOL
n

Root
name

Meth-

Eth-

Prop-

But-

Pent-

10

Root
name

Hex-

Hept-

Oct-

Non-

Dec-

Family name

- ol

EXAMPLE:

Name of alkane
:
Name of alcohol
:
Position of hydroxyl group
Full name of alcohol
:

propane
propanol
: carbon 1
propan-1-ol

Member

Number

Molecular

Structural

Name of

Name of

of

formula

formula

correspond-

alcohol

carbon

atoms, n
1

ing alkane

CH3OH

Methane

Methanol

C2H5OH

Ethane

Ethanol

C3H7OH

Propane

Propanol

ISOMERS OF ALCOHOLS
Exists in alcohols with 3 or more carbon atoms.
Results from:
a) branching of the carbon chain

Examples

: C4H9OH

b) Different locations of the hydroxyl group

Example: C3H7OH

NAMING ISOMER OF ALCOHOL

Step 1: Find the longest continuous carbon chain
containing the hydroxyl group
Step 2: Name the longest chain by substituting the
ending ol for the e of the corresponding alkane
Step 3: Number the carbon atoms beginning at the
end nearer to the hydroxyl group ensure that
hydroxyl group will be given the lowest possible
number

NAMING ISOMER OF ALCOHOL

Step 4: Identify the position of hydroxyl group by
writing the number of carbon atom to which it is
attached in front of the ending ol
Step 5: Locate the name all attached alkyl groups
Step 6: Complete name for the alcohol by
combining the three component parts together.
Write the name as a single word.

Which of the following represents a structural formula of an alcohol ?

Name the structure shown below.

The molecular formula of an alcohol that

contains three carbon atom is
A C3H6O
B C3H7OH
C C3H8OH
D C3H9O

What is the functional group for alcohol ?

What is the general formula for propanol ?

Draw the structural formulae of 2-methylbutan2-ol ?

Which of the following are isomers of butanol ?

I
Butan-3-ol
II 2-methylpropan-2-ol
III 2-methylpropan-1-ol
IV 3-methylbutn-2-ol
A
B
C
D

I and IV only
II and III only
I, II and III only
II, III and IV only

INDUSTRIAL PRODUCTION OF
ETHANOL

Ethanol , C2H5OH is one of the most important

alcohols.

It is manufactured on a large scale by two main

processes :
From sugars and starch by fermentation
From petroleum fractions by hydration

MAKING ETHANOL BY
FERMENTATION

The fermentation process is an anaerobic which

means it takes place in the absence of oxygen.
Yeast is added to sugar or starch and left in a
warm place for several days in the absence of air.
Yeast releases enzyme.
Enzymes break down the sugars and starches
into glucose, C6H12O6

In the fermentation process, the enzyme called

zymase.
Zymase slowly decomposes the glucose C6H12O6 to
form ethanol, C2H5OH and carbon dioxide, CO2.
C6H12O6 2CH3CH2OH + 2CO2

Temperature : 18 20 oC
Catalyst
: yeast (zymase)
Other condition :
absence of oxygen

When the concentration of ethanol formed

reaches about 15%, the yeast dies and the
fermentation stops.
It is impossible to produce pure ethanol by
natural fermentation.
Ethanol is then purified by fractional
distillation

MAKING ETHANOL BY HYDRATION

Is called catalytic hydration
An addition reaction combines ethene, C2H4 with
water to produce ethanol.

CH2=CH2 + H2O CH3- CH2OH

steam

Temperature : 300OC
Pressure
: 60 atm
Catalyst
: phosphoric acid, H3PO4

What is the process involved in the conversion of

propene to propanol ?

Diagram shows the

set up of the
apparatus for the
fermentation process.

Which of the following is the product obtain

from this process ?
I

III

II

Water

Carbon dioxide

IV

Ethanoic acid

I and II only

Ethanol

B
C
D

I and III only

II and IV only
III and IV only

LABORATORY PREPARATION OF ETHANOL

Aim : To produce pure ethanol through the

fermentation and distillation process
Materials : Glucose solution, yeast, lime water,
pipe water , porcelain pieces
Apparatus : 250cm3 conical flask, test tube,
rubber stopper with delivery tube, beaker,
spatula, round-bottomed flask, wire gauze, tripod
stand, Bunsen burner, thermometer, Liebig
condenser, rubber tube, retort stand

PROCEDU
RE

100cm3 of glucose solution is poured into the

conical flask
Add two spatulas of yeast into the glucose
solution
Prepare the apparatus arrangement as shown in
Diagram (a)
Leave the materials and apparatus at room
temperature for two to three days
Observe the changes that occur at the end of the
activity

Pour the products of the fermentation into the

distillation flask and heat it[Diagram b)
Collect the clear liquid that is distilled out from
the Liebig condenser
Record the temperature on the thermometer
when the clear liquid is distilled out
Observe the clear liquid and physical state of the
distilled product

OBSERVATION :

A colourless gas is liberated during the

fermentation process.
The gas turns lime water milky
A colourless liquid is obtained during the
fractional distillation

DISCUSSIO
N

Zymase, the enzyme from yeast, slowly

decomposes glucose in the absence of oxygen
to form ethanol and carbon dioxide
C6H12O6 2CH3CH2OH + 2CO2

The carbon dioxide released turns lime water

milky.
Fermentation occurs efficiently at a temperature
of 35OC when the activity of the enzyme is at its
peak.
Water and ethanol are two miscible liquids with
different boiling points.
Hence, both liquids have to separate by fractional
distillation.

CONCLUSION :

Ethanol can be obtained by the

fermentation of glucose found in sugars or
carbohydrate

The diagram shows the experimental set-up to

produce compound X.

What is compound X ?
A Ethane
C Ethanol
B Ethene
D Ethanoic acid

SUMMARY :
What is the general formula for alcohol ?
What is the functional group for alcohol ?
What is isomer ?
What is the processes to produce ethanol ?

NEXT CLASS :

Physical properties of alcohols

Chemical properties of ethanol
Uses of alcohols
Misuse and abuse of alcohol

Low boiling
point

Physical properties
of alcohols

Is a liquid
at room
conditions

Very
soluble in
water

Very soluble
in water

colourless

Low boiling
point

Highly
volatile

Physical
properties
of ethanol

Has
sharp
smell

Is a liquid at
room
conditions

CHEMICAL PROPERTIES OF
ETHANOL
Combustion
Oxidation

dehydration

COMBUSTION
Alcohols are very flammable substances.
Complete combustion of ethanol produces carbon
dioxide and water

2H5OH(l) + 2O2(g) 2CO2(g) + 3H2O(l)

Ethanol releases lots of heat

This makes ethanol suitable for use as a fuel
as a clean fuel because it does not release
pollutants into the atmosphere

OXIDATION

Oxidation reaction is very common

Occurs when a substance combines with
oxygen
Oxidizing agents are needed to carry out the
oxidation reactions

COMMON OXIDIZING AGENT

Acidified potassium dichromate(VI), K2Cr2O7

solution
Acidified potassium manganate (VII), KMnO4
solution

Alcohols can be easily oxidized to carboxylic

acids ( a family of organic compounds with COOH
group)
When acidified potassium dichromate(VI) ,
K2Cr2O7solution is added to ethanol the mixture
is warmed
It turns from orange to green
Shows it has oxidized the ethanol to form
ethanoic acid, CH3COOH

-CH2OH group has gained an extra oxygen

atom

Changed into a COOH group

Number of carbon atoms remains unchanged

If acidified potassium manganate (VII), KMnO4

solution is used
Changes colour from purple to colourless

DEHYDRATION

Remove water from a compound

In the dehydration alcohol, a molecule of water is
eliminated from each alcohol molecule
Alcohol molecule becomes an alkene molecule
This reaction can be used to make alkenes from
alcohol

Elimination of a molecule of water results in the

formation of a carbon-carbon double bond

Noticed that the hydroxyl group, -OH is removed

together with a hydrogen atom

The ethene produced can be detected by the

following tests :

Decolourizes reddish-brown bromine water

Decolourizes purple acidified potassium
manganate(VII), KMnO4 solution

Two methods to carry out the dehydration in

school laboratory :

Ethanol vapour is passed over a heated

catalyst such as unglazed procelain chips,
porous pot pumice stone or aluminium oxide,
Al2O3
Ethanol is heated under reflux at 170oC with
excess concentrated sulphuric acid

HOW DO OTHER ALCOHOLS REACT ?

Ethanol is a member of the alcohol

homologous series
All the other members of this series have the
same functional group which is the hydroxyl
group
Hence, other members of the family should be
able to exhibit similar chemical properties
as ethanol

SUMMARY

As

a solvent in
perfumes
Cosmetics
Toiletries
Properties
Colourless
Volatile

Miscible

of alcohol:

with water
Good organic solvent

As

a thinner in
lacquer
varnish
shellac
Ink
Properties
Colourless
Volatile

Miscible

of alcohol:

with water
Good organic solvent

As

a cleaner for
Compact disc
Video cassette recorder head
Properties
Colourless
Volatile

Miscible

of alcohol:

with water
Good organic solvent

As

a fuel
Clean fuel
biofuel
gasohol
Properties
Volatile
Highly

of alcohol:

flammable
High heat content

As

a raw material in the manufacture for

vinegar
fibre
explosive
plastic
Properties

of alcohol:
Chemically reactive

As

a raw material to make

pharmaceutical products
tincture
antiseptic
Cough syrup
Rubbing alcohol
Properties
Volatile
Good

of alcohol:

solvent
antiseptic

ALCOHOL MISUSE AND ABUSE

Human consuming ethanol in the form of

alcoholic drinks for centuries even though
doctors have reminded users about the harmful
effects of ethanol

Ethanol acts as a depressant on the central

nervous system
It slows down physical and mental activity
Causes person to feel high and to lose all
shyness

Person is no longer in control of his actions

Lose both physical and mental control

If driving a car, he can cause fatal accidents

Alcohol is also addictive

Long term excessive consumption will turn a
person into an alcoholic
Alcoholism creates social problems for the
family and society
cause chronic liver disease(cirrhosis) , brain
damage and leading to death

CARBOXYLIC ACID
Examples of common carboxylic acids :
Acetic acid in vinegar
Lactic acid in sour milk
Citric acid in citrus fruits
Ascorbic acid is vitamin C
Salicylic acid is used to make aspirin

Contain carbon, hydrogen and oxygen

Functional group : -COOH , carboxyl group

General formula : CnH2n+1COOH (n= 0,1,2,3)

NAMING CARBOXYLIC ACID

Straight-chain carboxylic acids are named by

replacing the e from alkane name with oic
acid

Step 1 : determine functional group / family

Step 2 : find the longest continuous carbon

Step 3 : name the longest chain by replacing ending

e of alkane name with oic acid
Step 4 : number the carbon atoms in the longest
chain beginning at the carboxyl group
Step 5 : locate and name all attached alkyl group

List the names and molecular formulae of first

four members of carboxylic acid
Draw structural formulae of the first four
members of carboxylic acid and name them using
the IUPAC nomenclature

MAKING ETHANOIC ACID

Most common : oxidation of an alcohol

Carried out by refluxing ethanol with an
oxidizing agent such as acidified potassium
dichromate(VI), K2Cr2O7 solution or potassium
manganate(VII), KMnO4 solution

The flask is fitted with an upright condenser to

prevent the loss of a volatile liquid by vaporization.
This method of retaining a volatile liquid during
heating is called refluxing

PHYSICAL
PROPERTIES

Colourless liquids at room temperature

Have sharp or unpleasant odours

Larger carboxylic acid molecules that have ten

or more carbon atoms are wax-like solids and
have little or no odour
Boiling point higher than alkane
Increase with increasing number of carbon atoms
per molecule

CHEMICAL PROPERTIES
Acid properties :
Ethanoic acid is a weak monoprotic acid

Only hydrogen atom in the carboxyl group COOH

can ionize in water to produce hydrogen ions, H+
Weak acid, partial dissociation occurs to produce
low concentration of hydrogen ions.
The presence of hydrogen ions turn moist blue
litmus paper red
Reacts slowly with metals, bases and carbonates

Reactions with metals

Reactions with bases

Reactions with carbonates

Reactions with alcohols

REACTIONS WITH
METALS

Dilute ethanoic acid reacts with reactive metals

to produce a salt and hydrogen.
Carboxylic acid + reactive metal
carboxylate salt + hydrogen
2CH3COOH + Zn Zn(CH3COO)2 + H2
A colourless solution of zinc ethanoate is formed

REACTION WITH BASES

Dilute ethanoic acid neutralizes alkalis to give an

organic salt and water
CH3COOH + NaOH CH3COONa + H2O
Carboxylic acid + base carboxylate salt +
water

REACTIONS WITH CARBONATES

Acids reacts with metal carbonate to produce a salt,

carbon dioxide and water
2CH3COOH +CaCO3Ca(CH3COO)2 +CO2 + H2O
Carboxylic acid +metal carbonate carboxylate salt +
carbon dioxide + water

REACTS WITH ALCOHOLS

Carboxylic acid reacts with alcohol to form an

ester and water
Reaction which produces an ester is called
esterification

CH3COOH + C4H9OH CH3COOC4H9 + H2O

Carboxylic acid + alcohol ester + water

CHEMICAL REACTIONS OF OTHER

CARBOXYLIC ACID

All member have the same functional group which

is carboxyl group, -COOH
Therefore, other carboxylic acids undergo the same
chemical reactions
Carboxylic acid + reactive metal carboxylate salt + hydrogen
Carboxylic acid + base carboxylate salt + water
Carboxylic acid +metal carbonatecarboxylate salt +CO2 + H2O
Carboxylic acid + alcohol ester + water

USES OF CARBOXYLIC ACIDS

Ethanoic acid : most important carboxylic acid

Ethanoic acid most commonly called acetic acid

Is a major industrial chemical

Use in food as a flavouring and as a preservative

Vinegar is a solution containing 5% ethanoic acid.

Ethanoic acid is also used with other chemicals to make :

Drugs
Dyes
Paints
Insecticides
plastics

In the rubber industry, methanoic acid

HCOOH (formic acid ) is used to coagulalate
latex.
Fatty acids are long-chain carboxylic acids used
in making soaps.
Carboxylic acids are used in the manufacture
of polyesters and polyamides which are fibres
used in the textile industry.
Benzoic acid is a preservative in foods

ESTER
S
Organic compound that are widely found in nature
Most are found in fruits.

Contain hydrogen, carbon and oxygen

General formula is CnH2n+1COOHCmH2m+1

n= 0,1,2,3,

m= 1,2,3,

Fuctional group : -COO (carboxylate group)

NAMING ESTERS

Name of alkyl
group from alcohol

Name of
carboxylate group
from carboxylate
acid

FORMATION OF ESTERS

Esterification

Carboxylic acid + alcohol ester + water

Catalyst : concentrated H2SO4

Example :
Propanoic acid + ethanol ethyl propanoate + water

PHYSICAL PROPERTIES OF
ESTERS

Sweet pleasant smell

Colourless liquids

Boiling points much lower than carboxylic acids

of similar molecular masses
Volatile
Slightly soluble in water but readily dissolve in
organic solvents

NATURAL SOURCES OF ESTERS

Found in fruits and flowers

IUPAC PROVIDES INFORMATION

ABOUT :

Which homologous series it belongs to

Its functional group

The total number of carbon atoms

present
Its molecular and structural formulae

USES OF ESTERS IN EVERYDAY

LIFE

Preparation of cosmetics and perfumes

As food additives to enhance the flavour and
smell of food

Simple esters

Larger esters

Solvents for :

Sunburn lotions

Nail polish removers

Glues

Production of soaps and

detergents
Production of polyester
(synthetic fabrics)

ARTIFICIAL FRUIT FLAVOURINGS

Ester

Formula

Flavour

n-pentyl ethanoate

CH3COOC5H11

Bananas

Ethyl butanoate

C3H7COOC2H5

Pineapples

Octyl ethanoate

CH3COOC8H17

Oranges

Isoamyl isovalerate

C4H9COOC5H11

Apples

Methyl salicylate

C6H4(OH)(COOCH3)

Oil of wintergreen

USES OF ESTER IN EVERYDAY LIFE

DESCENDING THE
HOMOLOGOUS SERIES

First member
Second member
Third member

As the number of carbon atoms per molecule increases :

Melting point increases

Boiling point increases

Density increases
Viscosity increases
Volatility decreases

FATS

WHAT ARE FATS AND OILS ?

Chemically very similar but differ in their physical

states.

Fats found in animals solid at room temperature

Examples : butter and tallow

Fats from plants are normally liquids called oil

Examples : palm oil, sunflower oil and coconut oil

Fat formed from :

carboxylic acid (fatty acids)

alcohol (glycerol @ propane-1,2,3-triol)

WHY ARE FATS AND OILS

IMPORTANT TO OUR BODY PROCESS
?
Provide us :
Energy
Nutrients
Thermal insulation
Protection to internal organs-kidney is protected
by a layer of fat

PROTECTION AND STRUCTURAL

ROLE

Surround and protect vital internal organs in

our body
Form the protective membrane of each cell

SOURCES OF ENERGY

Store energy as body fat

Release energy during cell respiration

THERMAL INSULATION

Fats under the skin act as a thermal insulator

which helps to keep our body warm

SOURCE OF NUTRIENTS

Help to carry fat-soluble vitamins like

vitamins A, D, E and K, which essential for good
health

SATURATED AND UNSATURATED

FATS

Affect by the parent fatty acids

Saturated fatty acid has all carbon atoms joined
together by carbon carbon single bonds.
Example : palmitic acid

UNSATURATED FATS

Unsaturated fatty acid that has carbon-carbon

double bonds

Monounsaturated :
has one carbon-carbon double bond
Example : oleic acid
Polyunsaturated :
Has more than one carbon-carbon double bond
Example : linoleic acid (2), linolenic acid (3)

Saturated fats :
Contain esters of glycerol and saturated fatty
acids

Unsaturated fats :
Contain esters of glycerol and unsaturated fatty
acids

CONVERTING UNSATURATED FATS

TO SATURATED FATS

Catalytic hydrogenation

Bubbling hydrogen gas through hot liquid oil

Catalyst: nickel
Temperature: 200 oC
Pressure: 4 atm

EFFECT FATS ON HEALTH

High in energy result in obesity- heart disease

and diabetes
Saturated fats- raise the level of cholesterolcauses fatty deposits-raise blood pressure
Hardening of the arteries occurs-arteriosclerosis
and cause heart attack

INDUSTRIAL EXTRACTION OF PALM

OIL

Two type of oil

- pulp palm oil
- kernel or seed palm kernel oil

ADVANTAGES OF USING PALM OIL

IN FOOD PRODUCTION

Cheaper oil : less expensive than other vegetable

oils
Better oil : can withstand heat and resist
oxidation (antioxidant) when cooked at high
temperature

HEALTHIER
OIL :
Easy digested and absorbed
Does not cause a rise in blood cholesterol level
Does not contain cholesterol
Contains omega-6 fatty acid (linoleic acid)
Reduce the incidence of coronary heart disease
Contains the highest amounts of natural antioxidants
(vitamin A and E)
To prevent aging, cancer, arteriosclerosis

PALM OIL INDUSTRY IN MALAYSIA

Malaysia is the worlds largest producer and

exporter of palm oil contributing 58% of the
worlds production

Importance of research :
Develop new products and uses for palm oil
Research institutes :
PORIM Palm Oil Research Institute of
Malyasia

RESEARCH PROJECTS

Conversion of palm oil into biofuels

Conversion of palm oil biomass into pulp and
paper
Production of biodegradable thermoplastics

NATURAL
RUBBER

NATURAL POLYMER

Polymer that exists naturally and is not made by

man from chemical reactions
Natural polymer

Monomer

Natural rubber

Isoprene

Starch

Glucose

Cellulose

Glucose

protein

Amino acid

Cotton and wood are made up of cellulose

Wool and silk are protein that found in nature

NATURAL RUBBER

From the latex secreted by rubber tree

White milk-like fluid

Called poly(isoprene)

Monomer is isoprene

COAGULATION PROCESS OF
LATEX

Latex needs to be turned into a solid to be used

in daily purposes

This process is known as coagulation

Latex is a colloid (aqueous solution)

It consists of rubber particles dispersed in

water

Each rubber particle is made up of :

many long-chain rubber molecules
enclosed by a protein-like membrane which is
negatively charged

Refer figure 2.37 page 93 text book

Coagulation of latex will occur when it is exposed

to air
This is because the bacteria from the air enter
the latex.
Bacteria produce lactic acid that causes
coagulation
Due to the slow bacterial action, coagulation
takes longer time.

ALKALI IS ADDED TO LATEX TO

PREVENT COAGULATION

Latex can be preserved in the liquid state if

ammonia solution is added
Ammonia solution contains hydroxide ions. OHthat neutralize the acid produced by the
bacteria.

Rubber particles remain negatively charged

Coagulation is prevented

PROPERTIES OF NATURAL RUBBER

White solid at room temperature
Elasticity decreases over time
Easily oxidized by air
Soft
Sensitive to heat :
When heated, it becomes soft and sticky
When cooled , it becomes hard and brittle

VULCANIZATION OF RUBBER

Vulcanization improve natural rubber properties

Vulcanization is a process whereby rubber is
reacted with sulphur
In industry, latex is heated with sulphur or rubber
products exposed to disulphur dichloride,S2Cl2
gas.

COMPARE AND CONTRAST THE PROPERTIES

OF VULCANIZED AND UNVULCANIZED
RUBBER
Similarities :
Elastic
Heat and electrical insulator

DIFFERENCE
S
Vulcanized

Differences

rubber

Unvulcanized
rubber

More elastic

Elasticity

Less elastic

Harder

Hardness

Softer

Stonger

Tensile strength

Weaker

Can withstand
higher temperature

Resistance to heat

Cannot withstand
higher temperature

Less easily oxidized

Resistance to

Easily oxidized

oxidation
Does not become soft
and sticky easily

Effect of organic
solvent

Becomes soft and

sticky easily

Vulcanization improve properties of natural

rubber due to the :
presence of cross-linkage of
sulphur atoms between the
rubber molecules

When vulcanized rubber is stretched and

released, the cross-linkage pull the chains
back to their original arrangement
This improves the elasticity and strength of the
rubber
The presence of sulphur cross-linkage increases
the size of rubber molecules, making more
resistant to heat and organic solvents

Vulcanized rubber has much lesser carboncarbon double bond

- Higher resistance to oxidation

USES OF NATURAL RUBBER

Making tyres
Footwear
Rubber threads
Rubber foam
Conveyor belts
Rubberized bitumen roads

Buildings in earthquake areas built on rubber

blocks or rubber bearings help absorb
vibration
Its impermeability to gas and liquid used in
gloves, tubes and hoses
Rubber combine with other materials such as
synthetic rubber and plastics tougher while
maintaining their elasticity
* aircraft tyres must be made from natural
rubber- can take tremendous stress, strength
and heat produced during landing and taking off