HSC CHEMISTRY LESSON PLAN 19

5.1.6 Explain the need for refluxing during esterification

Refluxing is the process of heating a reaction mixture in a container with a cooling condenser
attached vertically. Heating is necessary for the reactant molecules to reach the activation energy
for the reaction to occur.

Refluxing is necessary to prevent the loss of volatile reactants and products to the environment
(alkanols, alkanoic acids and esters are highly volatile) during heating. It allows the reaction to be
carried out at a higher temperature than would otherwise be possible due to the volatile reactants
and products. The alcohol vapours are also flammable and so having then in a vapour form near a
source of heat poses a safety risk.

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5.1.7 Outline some examples of the occurrence, production and uses of esters

Esters are produced and found extensively in nature. An ester is an organic compound formed
through the reaction of an alkanol and alkanoic acid:

Alkanol + Alkanoic acid ↔ ester + water

It is produced in the presence of a concentrated H2SO4 acid catalyst and heated to enable
equilibrium to be achieved much quicker. It is then refluxed during production and further purified in
a separating funnel. Many of the odours and flavours of fruits are caused by the presence of esters.
Solid animal fats and plant oils are also natural esters. Some esters are used in industry as solvents
and thinners as they are able to dissolve polar and non-polar substances.

An example of an ester produced naturally and synthetically is methyl salicylate (C8H8O3) which is
also known as oil of wintergreen. It occurs as a natural product of many tree species such as
wintergreens where it provides protection against herbivores. It is also produced commercially from
the condensation reaction of salicylic acid and methanol

CH3OH + C6H4(OH)COOH H2O + CH3COOCOHCHCHCHCH

Methyl salicylate is used as a flavouring agent and to provide fragrance to various products such as
shampoos and toothpaste.
Another example of an ester is ethyl ethanoate (C4H8O2) which is found in many fruits such as grapes
and wines. It is produced from the esterification reaction between ethanoic acid and ethanol.
i.e. CH3CH2OH(aq) + CH3COOH(aq) CH3COOCH2CH3(aq) + H2O(l)

It is used widely used in nail polish removers and varnishes and it is used to decaffeinate coffee
beans and in confectionary due to its fruity smell.

Mixing natural esters or synthetic esters can also produce cosmetics and flavours in foods. Esters
produced in industry may be used for various applications:
 Ethyl Butanoate is used as a strawberry flavouring in foods
 Acetyl Salicylic acid is used in medicine as aspirin
 Pentyl Ethanoate is used as a banana flavouring in foods
 Octyl Ethanoate is used as an orange flavouring in foods
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5.2.1 Identify data, plan, select equipment and perform a first-hand investigation to prepare an ester
using reflux

Method

1. Place 10mL of acetic acid, 20mL of 1-pentanol and 6-7 drops of concentrated sulfuric acid into a
round bottom conical flask
2. Add 2 or 3 boiling chips
3. Set up a refluxing apparatus (with a heating mantle)
4. Begin to heat the flask with the mantle, the mixture should boil for about half an hour to reach
an equilibrium mixture of alcohol, acid, ester and water
5. Remove the heating source and allow the mixture to cool for approximately 10 minutes. Using a
towel, hold either side of the joint of the condenser and flask. Separate the condenser and flask
by pulling apart and twisting in one movement
6. Transfer the mixture to a separating funnel containing water of about the same volume as the
mixture. Shake the contents and allow the layers to separate. The lower layer contains water
soluble acid and an alkanol acid can be run off and discarded. Esters cannot hydrogen bond so
have low water solubility
 7. Add sodium carbonate to neutralise the H2SO4 in the separating funnel until no more reaction
with the acid occurs. Add an equal amount of water to dissolve any salts Shake, stand and let
layers separate and then discard the lower aqueous layer
8. Detect the ester (can be distilled first) by smell.
9. Repeat experiment 10 times and if similar results are obtained then the experiment can be
deemed reliable.

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5.2.2 Process information from secondary sources to identify and describe the uses of esters as
flavours and perfumes in processed foods and cosmetics

Esters are widely used as flavours and perfumes in processed foods and cosmetics. Esters such as
ethyl methanoate are fruity and rum like and so are used as flavouring and food additives in foods
such as cereals and dried fruits. Other useful esters include:

 Methyl Butyrate have an apple-like odour and so are used as flavouring agents in foods such
as chewing gum and apple pies.
 Ethyl Ethanoate is sharp, ether-like and has a wine/brandy odour which makes it useful in
the manufacture of cosmetics such as perfumes and also as a nail polish remover.
 Benzyl Ethanoate has a very pleasant, flower-like odour which makes is suited for use as a
jasmine fragrance.
Many glycerol containing esters are non-toxic, non-irritating and odourless which makes them useful
in the cosmetics industry for use as moisturizing agents and emollients in toiletries such as
deodorants.

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Questions

1. Assess the validity and accuracy of the first hand investigation used to make an ester (4 marks)

2. Describe an ester that is used in cosmetics and an ester used in food. (3 marks)