SUBTOPIC: ESTERS

Functional group

O
R-C-O-R’
1) Name of functional group:
2) Name of family:
3) Uses:
a. Short chain esters
i. food flavouring compounds
ii. perfumes
b. long chain esters
i. animal fats
ii. vegetable oils

Nomenclature
1) Identify parent chain, which is the longest continuous carbon chain containing ester fg
2) No need to designate the position of ester fg bc it always assume position no 1.
3) Replace the suffix ‘ane’ with ‘oate’
a. Eg:

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Physical properties
Solubility in water

1) The possible hydrogen bonds btw esters and water is not very extensive
2) Alkyl group hinders water molecules from coming close
3) Therefore form hydrogen bond at a distance (weak hydrogen bond)
4) Esters are sparingly soluble in water compared to carboxylic acids and alcohols.
5) Water solubility decreases with increasing molecular mass

Boiling points/melting points

1) Bp of esters are lower than bp of alcohols and carboxylic acid
2) Esters are polar cpds but they cannot form strong hydrogen bonds to each other
3) Diagram:

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Physical state
- Lower esters may be volatile
-Higher esters are less volatile

Chemical properties
Formation of esters
1) The name of chemical reaction is ‘ESTERIFICATION’
2) The type of reaction is condensation reaction
3) Esters can be prepared from carboxylic acids and alcohols
4) 3 stages are involved in the preparation of an ester
a. esterification (using reflux apparatus)
i. A carboxylic acid and an alcohol are placed in the round bottom flask with anti-
bumpings .
ii. Concentrated sulfuric acid is added as a catalyst to speed up the rate of reaction
iii. Then they are heated under reflux for half an hour
iv. Diagram:

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b. Separation/Isolation (using separating funnel)
i. A mixture of ester, unreacted carboxylic acid and unreacted alcohol are placed
in the separating funnel

ii. Firstly, add distilled water into separating funnel to remove water-soluble
impurities.
iii. Shake the separating funnel
iv. Discard the aqueous layer (bottom layer)

v. Then, add sodium carbonate solution into the separating funnel to react with
sulfuric acid and unreacted carboxylic acid

Equations:

vi. Shake the separating funnel and release carbon dioxide gas periodically by
opening the stopcock
vii. Identify aqueous layer by adding few drops of water
viii. Discard aqueous layer (bottom layer)
ix. Add distilled water to remove any remaining water soluble impurities
x. Discard
xi. Add fused anhydrous calcium chloride (acts as drying agent) into ester to
remove traces of water

c. Purification (using distillation apparatus)

i. Place impure ester into another round bottom flask with few anti-
bumpings/boiling chips.
ii. Set up distillation apparatus
iii. Distill the ester at its boiling point
iv. Collect pure ester in a receiver (as distillate)
v. Diagram:

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Hydrolysis of ester
1) Acidic hydrolysis
a. Ester can be hydrolysed into carboxylic acid and alcohol in the presence of acid
b. Acid such as sulfuric acid, is used as catalyst to speed up the rate of reaction
c. Acid is used in trace amount
d. Equation:

2) Alkaline hydrolysis
a. Ester can be hydrolysed into carboxylate ion and alcohol in the presence of alkali
b. The common alkalis used are NaOH and KOH
c. Equation:

d. Carboxylic acid is formed from carboxylate ion by adding dilute strong acid such as HCl
e. Equation

f. Alkaline hydrolysis is used in soap-making

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 SUBTOPIC: TRIGLYCERIDES

1) Lipids – a family of cpds, which are non-polar in nature and insoluble in water
2) Lipids can be classified into 3 classes
a. Triglycerides
b. Waxes
c. Steroids

3) Triglycerides are naturally occurring esters

4) General structure of a triglyceride molecule

Examples:

5) A triglyceride is derived from 1,2,3-propantriol and various carboxylic acids

6) Carboxylic acids have long hydrocarbon chain with even no of carbon atoms ( C12-C22) and have
no branches are known as fatty acids.

7) Triglycerides can be divided into fats and oils

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Physical properties

FATS OILS

Origin
Land animals Plants/ marine animals

Physical state
solid
• Contain many C-C bonds in HC
chain/high degree of saturation in HC
chain
• Regular nature of HC chains
• Can be packed neatly into a solid lattice
• Easier to set up more DF between HC
chains
Liquid
• Many C=C bonds in HC chain/unsaturation
in HC chain
• irregular nature of HC chains
• Cannot be packed neatly into a solid lattice
• Difficult to set up DF between HC chains

Melting point/boiling point

High
• Contain many C-C bonds in HC chain
• Regular nature of HC chains
• Can be packed neatly into a solid lattice
• Easier to set up more DF between HC
chains
• A lot heat required
Low
• Many C=C bonds in HC chain
• irregular nature of HC chains
• Cannot be packed neatly into a solid lattice
• Set up weak/less DF between HC chains
• less heat required

Solubility in water
insoluble Insoluble

Solubility in non-polar organic solvent

soluble soluble

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Chemical properties
1) Formation of a triglyceride

Example:

2) Hydrolysis
a. Acid hydrolysis

Example:

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 b. Alkaline hydrolysis

Example:

3) Hydrogenation
a. A process to convert oils into solid fats in the presence of high temperature, pressure and
Nickel catalyst

b. Addition reaction using hydrogen gas

c. Used in the making of margarine
d. In hydrogenation reaction, some or all multiple covalent bonds are converted into single
bonds

4) Determination of the degree of unsaturation in fats/oils

a. Addition reaction using bromine solution
b. The degree of unsaturation is quoted in ‘Iodine Number”
c. Iodine No = the amount of Iodine exactly reacted with 100g fats or oils
d. Use volumetric analysis (titration) to measure the degree of unsaturation
e. The endpoint is reached when there is a permanent colour change from colourless to
orange brown

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f. The more bromine solution added, the greater the no of multiple bonds present in fats or
oils
g. Calculations:

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