ALKANOLS (Alcohols)
This is a homologous series whose general formula is CnH2n +1OH where n = 1, 2, 3
Alcohols are identified by having an O–H group in the molecule.
The OH group is called the hydroxyl group and it is a functional group of alcohols. The
OH group of alcohols is the reactive part. The names of alcohols end with an –ol e.g.
methanol, ethanol, propanol
Alcohols Molecular formula Structural formula Boiling point (0C)
Methanol CH3OH 65
Ethanol C2H5OH 78
Propanol C3H7OH 97
Butanol C4H9OH 117
pentanol C5H11OH 137
N:B The boiling point increases with an increase in the number of carbon atoms
Isomers of alcohols
There are different isomers of the alcohols propanol, Butanol and pentanol.
The two isomers of propanol are shown below.
propan-1-ol propan-2-ol
The naming of alcohol depends on the position of –OH group in the structure
ETHANOL
Ethanol is not a hydrocarbon because the molecule contains oxygen as well as hydrogen
and carbon.
Ethanol is a colorless liquid which boils at 78 °C. It is completely miscible with water.
Production of ethanol by fermentation ( Anaerobic respiration)
Ethanol is produced from glucose or any carbohydrates. Zymaze in yeast is used as a
catalyst. During fermentation, the glucose is converted to ethanol and carbon dioxide in
the absence of oxygen.
C6H12O6 2C2H5OH + 2CO2
Production of ethanol by catalytic reaction of steam and ethene
The main raw material is crude oil from which alkanes are produced. The alkanes are
then cracked to produce ethene.
Ethane is then reacted with steam at a temperature of about 3000C in the presence of a
catalyst (H3PO4) and a pressure of 70 atm. It is a continues process.
A continuous process means that reactants are constantly being put in at one end of the
reaction vessel and products are constantly being taken out at the other end of the
reaction vessel. Adding the components of water across the double bond of ethene is
called the hydration of ethene.
Advantages and disadvantages of the two methods of making ethanol:
Advantages of fermentation:
Cheap and renewable resource like sugar cane, sugar beet
Disadvantages of fermentation:
Slow reaction and made by an inefficient batch process, poor quality product e.g. low
aqueous concentration, other organic chemicals formed to and yeast cell residues to
remove. Large areas of agricultural land are needed.
Advantages of ethene route:
Fast and efficient continuous process, relatively pure product, country may have local oil
supply (e.g. North Sea for UK, Middle East countries)
Disadvantages of ethene route:
Using a non-renewable finite resource (crude oil/cracking)
Properties of ethanol
a) It is a clear colorless liquid which boils at 780C]
b) It dissolves or mixes in water
c) It burns in air to produce a lot of heat energy, water and carbon dioxide
C2H5OH + 3O2 CO2 + 3H2O + Heat energy
d) It reacts with sodium metal to form the salt, sodium ethanoate and hydrogen gas
C2H5OH + Na C2H5ONa + H2
Sodium ethanoate
Sodium ethoxide
e) Ethanol is oxidized to form ethanoic acid
Acidified potassium dichromate (VI) is used as an oxidizing agent
CH3CH2OH + 2[O] CH3COOH + H2O
f) Ethanol is dehydrated by concentrated sulphuric acid to form ethene
Ethanol Ethene + Water
C2H5OH(l) C2H4(g) + H2O(l)
Uses of ethanol
1) To make alcoholic drinks e.g. beer, wine, whisky
2) As a solvent in perfumes, varnish and paints
3) As a fuel: it can be mixed with methanol form methylated sprit
ALKONOIC ACID ( Organic acid)
This is a homologous series whose names end with an -ioc e.g. methanoic, ethanoic,
propanoic. Their general formula is CnH2n+1COOH
The functional group of carboxylic acid is –COOH which is called a carboxyl group
Alkanoic acid Molecular formula Structural formula
Methanoic HCOOH
Ethanoic CH3COOH
Propanoic C2H5COOH
Butanoic C3H7COOH
pentanoic C4H9COOH
Commonly occurring Alkanoic acids
Alkanoic acid source use
Tartaric acid from grapes in cooking
Ethanoic acid from oxidation of ethanol to produce vinegar
Ascorbic acid From fruits and vegetables In drugs for a healthy body
Citric acid From citrus fruits, and some
drinks
Properties of Alkanoic acid
1) Organic acids react reversibly with alcohols to form a sweet smelling substance
called an ester. The reaction of ethanol and ethanoic acid produces and ester cal
ethyl ethanoate and water. This is type of reaction used to produce polyesters by
condensation polymerization
2) They turn blue litmus paper red
3) Organic acid is a weak electrolyte as it can conduct electric current by the
movement of its ions.
4) They react with alkalis, forming a salt and water
CH3COOH + NaOH CH3COONa + H2O
5) They react with carbonates or hydrogen carbonates to produce a salt, water and
carbon dioxide
CH3COOH + Na2CO3 2 CH3COONa + CO2 +H2O
Sodium ethanoate
6) Organic acids react with metals to form a salt and hydrogen gas
2 CH3COOH + Mg (CH3COO)2Mg + H2
7) They produce hydrogen ion, H+ when dissolved in water. A few hydrogen ions
are produced and this makes them weak acids
CH3COOH + H2O CH3COO- + H+
Formation of Alkanoic acids ( e.g. ethanoic acid)
1) By the oxidation of ethanol using atmospheric oxygen.
The bacterial oxidation of ethanol to ethanoic acid has been a problem for one
product. The bacteria use air to oxidize ethanol in wine producing a weak solution
of ethanoic acid (acetic acid/ common vinegar)
2) Oxidation of ethanol by acidified potassium dichromate
Ethanol can be oxidized to produce ethanoic acid
K2Cr2O7
C2H5OH CH3COOH
Ethanoic Acid.
When ethanol reacts with oxygen it forms a weak acid called ethanoic acid. This can
happen naturally in the presence of bacteria, and it is the ethanoic acid which makes beer
or wine taste sour.
Ethanol + oxygen ethanoic acid + water.
C2H5OH(aq) + O2(g) CH3CO2H(aq) + H2O(l)
Ethanoic acid is a weak acid.
It is found in vinegar ("vinegar" is Old French for "sour wine").
Vinegar is used as a food flavouring and preservative.
Ethanoic acid is used to make a polymer called acetate rayon.
Acetate rayon fibres can be woven to make clothing and fabrics.
Structure of ethanoic acid.
Ethanoic acid will react with alcohols, alkalis, carbonates and metals.
Carboxylic Acids - Reaction with Alcohols - Esterification
When a carboxylic acid reacts with an alcohol in the presence of concentrated sulphuric
acid, an ester is formed. Concentrated sulphuric acid is a catalyst for this reaction.
An ester is a sweet smelling substance. Some esters are used as food flavorings (for
example in pear drop sweets).
Other esters are used as fragrances or perfumes.
Ethanoic Acid - Reaction with Alcohols.
Ethanoic acid will react with alcohols in the presence of
concentrated sulphuric acid, to form esters.
Concentrated sulphuric acid is a catalyst for this reaction.
Methanol + ethanoic acid methyl ethanoate + water.
CH3OH(aq) + CH3CO2H(aq) CH3CO2CH3(aq) + H2O(l)
Structure of methyl ethanoate.
Ethanol + ethanoic acid ethyl ethanoate + water.
C2H5OH(aq) + CH3CO2H(aq) CH3CO2C2H5(aq) + H2O(l)
Structure of ethyl ethanoate.
Propanol + ethanoic acid propyl ethanoate + water.
C3H7OH(aq) + CH3CO2H(aq) CH3CO2C3H7(aq) + H2O(l)
Structure of propyl ethanoate.
Butanol + ethanoic acid butyl ethanoate + water.
C4H9OH(aq) + CH3CO2H(aq) CH3CO2C4H9(aq) + H2O(l)
Esters occur widely in nature and are usually sweet/pleasant smelling liquids and widely
used as fragrances (e.g. perfumes) and food flavourings.
