OLevel Organic Chemistry Brief Study Notes

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.
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. Temperature is important in fermentation.
(b) Addition of steam to ethene at high temperature (300oC) and pressure (67 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
(c) Esterification
Combustion of alcohols
Alcohols burn in oxygen to produce carbon dioxide and water.
C2H5OH + 3O2 2CO2 + 3H2O
Oxidation of alcohols
Alcohols are oxidised to carboxylic acids.
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.
Esterification
Alcohols react with organic acids to form esters. Esters are sweet fruity-smelling
compounds.
Word equation :
Alcohol + carboxylic acid ester + water
Uses of ethanol
As a solvent
As a fuel
As a constituent of wine and beer
Human consumption of wine and beer can lead to alcohol addiction.
A model of an ethanol molecule
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.
CH3CH2OH + 2[O] CH3COOH + H2O
The orange dichromate (VI) solution changes from orange to
green.
A vinegar smell is detected.
Reactions of carboxylic acids
Two important reactions of carboxylic acids are :
Acid reactions
Esterification
Acid reactions
- 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 + 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.
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.
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.
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
Nylon
Terylene

Formation of Nylon
The monomers used are carboxylic acids and amines
The monomers are joined together by amide linkages 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. A
molecule of water is also eliminated. Terylene and nylon are examples of
condensation polymers.
Uses of Nylon and Trylene
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
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.