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Alcohols
Introduction

• Alcohols are a family of organic compounds containing carbon , hydrogen and oxygen.

• The general formula of alcohols is CnH2n+1OH (n = 1, 2, 3, 4…)

• The reacting group (or functional group) is the hydroxyl group, -OH.

• The names of an alcohol end with –ol.

• Propanol has 2 isomers. Isomers have the same molecular formula but different
structural formulas.

Formation of ethanol

• Ethanol is obtained by

• (a) fermentation

• (b) catalytic addition of steam to ethene

• (a) Fermentation breaks down the sugar into ethanol and carbon dioxide. Yeast is used
as a catalyst.

• C6H12O6  2C2H5OH + 2CO2

Sugar ethanol

Temperature of 37oC is used. A higher temperature of 45oC can denature and destroy the
yeast (which is a fungi).Temperature is important in fermentation.

• (b) Addition of steam to ethene at high temperature (300oC) and pressure (65 atm)
produces ethanol. Phosphoric acid is used as a catalyst.

• CH2=CH2 + H2O  CH3-CH2OH

Reactions of alcohols

• Alcohols undergo 3 important reactions:

• (a) Combustion

• (b) Oxidation
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• (c) Esterification

Combustion of alcohols

• Alcohols burn in oxygen to produce carbon dioxide and water. Many organic
compounds, when combusted, produce carbon dioxide and water.

• C2H5OH + 3O2 2CO2 + 3H2O

Oxidation of alcohols

• Alcohols are oxidised to carboxylic acids. Oxidation is the addition of oxygen.

• The number of carbon atoms remain the same in oxidation.

• CH3CH2OH + 2[O] CH3COOH + H2O

• The oxidation is carried out by using

• (i) oxygen

• (ii) acidified K2Cr2O7

• (iii) acidified KMnO4

Oxidation of alcohols

• During the oxidation:

– Acidified K2Cr2O7 turns from orange to green

– acidified KMnO4 is decolourised. (more preferred as potassium dichromate(VI)

is toxic)

Esterification

• Alcohols react with organic acids to form esters. Esters are sweet fruity-smelling
compounds.

• Word equation :

• Alcohol + carboxylic acid -> ester + water

Ethanoic acid (CH3COOH) reacts with ethanol to form CH3COOC2H5. The catalyst for this
reaction is concentrated sulfuric acid at 60oC under reflux.

Uses of ethanol

• As a solvent
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• As a fuel

• As a constituent of wine and beer

• Human consumption of wine and beer can lead to alcohol addiction.

• Ethanol, C2H5OH, is used in beer making.

Carboxylic Acids

• Carboxylic acids are a family of organic compounds containing carbon, hydrogen and
oxygen.

• The general formula of carboxylic acids is CnH2n+1COOH (n = 0, 1, 2, 3, 4…)

• The functional group is the –COOH group.

• Carboxylic acids end with –oic acid.

Carboxylic acid

• Butanoic acid has 2 isomers.

• Formation of ethanoic acid

– Ethanoic acid is formed by the oxidation of ethanol.

• By using atmospheric oxygen:

• CH3CH2OH + O2  CH3COOH + H2O

• By using acidified K2Cr2O7 or KMnO4.

• CH3CH2OH + 2[O]  CH3COOH + H2O

• The orange dichromate (VI) solution changes from orange to green.

• A vinegar smell of ethanoic acid is detected.

Reactions of carboxylic acids

• Two important reactions of carboxylic acids are :

– Acid reactions

– Esterification

Acid reactions
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- A carboxylic acid is a weak acid. When dissolved in water, it dissociates to

produce H+ ions.

- Eg. CH3COOH <--> CH3COO- + H+

Reactions of carboxylic acids

• Carboxylic acids react with bases to form salt and water only.

• Carboxylic acids react with carbonate to produce carbon dioxide gas.

Reaction of acid - Esterification

• In the presence of a catalyst concentrated sulfuric acid, carboxylic acids react with
alcohols to form a sweet-smelling compound, called an ester.

• Eg. Ethanoic acid + ethanol  ethyl ethanoate (an ester) + water

Esters

• The functional group of an ester is –COO- (there is a C=O bond and a C-O bond; refer
to textbook on how the ester functional group looks like)

Esters are produced when an organic acid reacts with an alcohol, with a catalyst that is
concentrated sulfuric acid under reflux.

Organic acid + alcohol  ester + water

Esters

• Esters are neutral compound with a sweet smell.

• Esters are present in fruits.

• Uses of esters

– Artificial flavouring

– Solvents for organic compounds

– Vegetable oils

Macromolecules

• Macromolecules are very large molecules built up from joining together thousands of
small units.
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• The process of joining together thousands of small units is called polymerisation.

• The small units are called monomers.

• The large molecule formed is called a polymer.

• There are 2 groups of macromolecules:

• - synthetic polymers

• - natural macromolecules

Synthetic Polymers

• These are man-made polymers made by

–Addition polymerisation

–Condensation polymerisation

• Polymers made from addition polymerisation are called addition polymers.

• Polymers made from condensation polymerisation are called condensation polymers.

Addition Polymers

• Addition polymers are made from unsaturated monomers.

• The monomers are linked ( or added ) together to form a large molecule without the
loss of any atoms. The monomers are joined together by an ADDITION reaction.

• Plastics are addition polymers formed using alkene molecules as monomers.

• Poly(ethene) is made from ethene monomers.

nC2H4  -(-CH2-CH2-)-n

Condensation Polymers

• Condensation polymers are made from monomers containing alcohol, carboxylic acid
or amino (-NH2) functional groups.

• The monomers are linked together to form a large molecule with the ELIMINATION
of small molecules like water. The monomers are joined together by a condensation
reaction.

Examples of condensation polymers

• Two examples of condensation polymers are

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– Nylon

– Terylene

Formation of nylon

• The monomers used are carboxylic acids and amines

• The monomers are joined together by amide linkages (-CONH-) to form a polyamide.
A molecule of water is eliminated.

Formation of Terylene

• The monomers used are carboxylic acids and alcohols.

• The monomers are joined together by ester linkages to form a polyester (Ester linkage :
-COO-) A molecule of water is also eliminated. Terylene and nylon are examples of
condensation polymers.

Uses of nylon and terylene

• Nylon and terylene are made into synthetic fibres.

• Nylon fibres are used to make ropes, fishing lines, strings for rackets and cloth for
making raincoats, tents and parachutes.

• Terylene fibres are used to make clothings.

Pollution caused by plastics

• Plastics are non-biodegradable and cannot be decomposed by bacteria in the

environment.

• Plastic objects accumulate and pollute the environment.

• Plastics are carbon-based polymers which burn easily to release toxic fumes.

Natural Polymers (out of syllabus)

• Natural polymers are important substances found in all plants, animals and food.

• Food is made up of 3 types of polymers:

– Proteins needed for growth

– Carbohydrate which provide the body with energy

– Fats which also provide the body with energy.

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