M4 CHEMISTRY

S2 Q4 : Organic Chemistry
ESTER

Global context Key concept Related concept

Patterns and Models System Personal and Cultural Expression

Statement of Inquiry
Scientist discern different patterns of organic compounds into families with similar forms and
follow the same patterns when reacting with other substances to form a system with rules which
help to explain how it works in real world situations..
 KUD
K
1. Describe the carboxylic acid as a homologous series containing the –COOH
group.
2.Draw the structures of alcohol, C1 to C5, and name the unbranched carboxylic
acid,

U
Physical and chemical properties of carboxylic acid

Discussion on the pros and cons between fermentation process and hydration
process
 Esters
• Esters: A group of organic compounds that all contain
the same functional group -COO- with these common
properties:

• They are volatile (liquids that evaporate easily)

• They have a distinctive odour (‘fruity’ smell)
 Esters
• According to the IUPAC system the alcohol part of
the ester (R΄) is named first.
Nomenclature
Name the alcohol part
1st . R as an alkyl group.
2. Name the acid part by changing the ‘-ic acid’
to ‘-ate’.
Nomenclature
Naming of Esters
 Formation of ethyl ethanoate
Carboxylic acids will react with alcohols in the presence of an acid catalyst to form
esters.
Example: Ethanoic acid will react with ethanol in the presence of concentrated
sulfuric acid (catalyst) to form ethyl ethanoate:
The formation of ethyl ethanoate:
 Properties of Esters

• These properties of esters make them useful for food colorings

and perfumes:
• Volatility: Esters are very volatile as they only have weak
attractive forces between their particles so can evaporate easily
(readily change from a liquid to a gas).
• Soluble in water
• Distinctive smell: Esters are chemicals with pleasant ‘fruity’
smells, e.g. pentyl butanoate smells of strawberries.
 Structural and Displayed Formulae of Esters
• An ester is made from an alcohol and carboxylic acid.
• The first part of the name indicates the length of carbon chain of the alcohol, and it
ends with the letters ‘- YL ‘
• The second part of the name indicates the length of carbon chain of the carboxylic
acid, and it ends with the letters ‘- OATE ‘.
 Preparation of Ethyl Ethanoate

Statement of Inquiry
Scientist discern different patterns of organic compounds into families with similar forms and
follow the same patterns when reacting with other substances to form a system with rules which
help to explain how it works in real world situations..
 HYDROLYSIS
• Ester molecules undergoes hydrolysis to form carboxylic acids or
carboxylate salts and alcohols.
• Hydrolysis occurs in either acidic or basic condition.
• The reaction with pure water is so slow.
• The reaction is catalyzed by dilute acid such as HCl or H2 SO4 and heated
under reflux.
 Exit Task
Identify the esters which produce the following flavours

Flavours Ester

Banana

Pineapple

Grapes

jasmine

raspberries

oranges

apples
Self Assess 1
Self Assess 2
 Fats and Oils
• Non-Hydrocarbon – Fats

• 1. Fats are non-hydrocarbons which contain

carbon, hydrogen and oxygen atoms.

• 2. Fats (lipids / triglycerides) are belonging to the

group in ester.

• 3. Natural esters are formed from glycerol and fatty

acids.
 Fat

Animal fats have higher percentage of saturated fatty acids than unsaturated fatty acids.

Plant oils have higher percentage of unsaturated fatty acids than saturated fatty acids.
 Physical properties of fats

Fats (animal) in general are solids at room temperature and acted as:

thermal insulator
protective cushion to protect the vital organ
provide energy and stored in body
carry Vitamin A, D, E, K (insoluble in water)
Example: butter, fish oil (liquid in room temperature)
Fats (plant) are called oils. Oils are liquids at room temperature.
Example: olive oil, peanut oil, palm oil and bran oil
 Chemical properties of fats

Chemical properties of fats

• Unsaturated fats can be converted into saturated fats by hydrogenation (additional

reaction) in 200°C and 4 atm in the presence of nickel catalyst.
• Example: production of margarine from sunflower oil of palm oil.
Effect of fats

Fatty food produce high energy but high consumption of fatty food will results:

• obesity
• raise the level of cholesterol
• deposition will cause block the flow of blood which lead to stroke and heart attack
 Palm oil
It is extracted from fresh oil palm fruits.
• Palm oil – extracted from the pulp of the fruits.
• Steps in extraction of palm oil:

• sterilising (oil palm fruit)

• stripping

• digestion (crushing the husk and fruit and separate the oil by heating)
• squeezed out the oil
• extraction (separate the oil from water)
• purification the oil (palm oil is treated with phosphoric acid and then
steam is passed through to separate the acid)
• vacuum
 Natural rubber
• Natural Rubber
• Natural rubber is a natural polymer.
• Latex is a milk like liquid that flows out after
the bark of the rubber tree is cut. Latex is
mixture of rubber particles and water.
• Formula of natural rubber is (C5H8)n, where n
is about 10,000.
• Monomer of natural rubber is C5H8, known as
2-metylbut-1,3-diene (isoprene)
 Coagulation of Latex
• Each rubber particle consists of rubber molecules which are
enveloped by protein membrane.
• Protein membranes are negatively charged on its outer
surface.
• Like charges repel. The repelling force exists between the
rubber particles which cause the particles to be separated
from one another.
• This prevents the bonding of rubber particles and thus
prevents coagulation of latex.
 However, latex can coagulates if:

• Acid such as ethanoic acid is added to it.

• When acid is added to latex, the hydrogen ions from the acid neutralise
the negative charges on the surface of the protein membrane. The
neutral particles no longer repel each other. These rubber particles may
collide with each other, causing the membrane to break. The rubber
polymers are freed and they coagulate by combining together to form
large lump of rubber polymer. The latex has coagulated.
• the latex is left aside for 1 – 2 days. This is due to bacterial action on
latex. The activity of bacteria in the latex produces lactic that contains
hydrogen ions which causes coagulation of latex.
• Coagulation of latex can be prevented by adding alkali to it. The OH–
ions from the alkali will neutralise any acids that may be produced by
the bacteria.
 Vulcanization of Rubber

• Natural rubber is vulcanized to improve its characteristics so

that its usage could be wider.
• Vulcanised rubber is rubber that has been heated with
sulphur.
• Vulcanised rubber is prepared in the laboratory by soaking
the rubber in a solution of disulphur dichloride or sulphur
monochloride in methylbenzene.
• Rubber molecules have double covalent bonds.
• Sulphur atoms react with the double bond in the rubber
molecules chain to form C-S-S-C cross link between the
rubber molecules.
Natural Rubber vs Vulcanised Rubber