ALCOHOLS

ALCOHOLS

 Example : wine is made from grape

juice and rice wine is from fermented
rice
 Familiar alcohol : ethanol, C2H5OH
 The alcohol family

 Contain C, H and O
 Organic compounds
 Contain hydroxyl group, -OH as the
functional group
– This group is covalently bonded to a carbon
atom as shown below

– -C-O-H

 No OH- in an alcohol molecule. Alcohols

do not show alkaline properties.
 Neutral compounds
 The alcohol family

 One H atom in an alkane is replaced

by the hydroxyl group, an alcohol is
formed
 R-H R-OH
 CnH2n+1H CnH2n+1OH
 General formula = CnH2n+1OH
n = 1, 2, 3, …….
 Naming alcohols

 The names of straight chain alcohols

can be derived from those of the
alkanes.
 Replacing the ending -e from the
name of the alkane with –ol.
 A number in front of the –ol to
indicate which carbon atom the
hydroxyl group is attached to.
 Naming alcohols
HHH
H- C-C-C-H
1 2 3
OHH H
 Name of alkane : propane
 Name of alcohol : propanol
 Position of hydroxyl group : carbon 1
 Full name of alcohol : propan-1-ol
 ISOMERS OF ALCOHOLS
Example: C4H9OH
H HHH H H H H
 H-C- C-C-C-H H-C -C- C- C-H
OHH H H H OHH H
Butan-1-ol Butan-2- ol

H CH3H H CH3H
H-C-C - C-H H-C-C - C-H
H OH H H H OH
2-methylpropan-2 ol 2-methylpropan-1 ol
 INDUSTRIAL PRODUCTION
OF ETHANOL

 Ethanol – most important alcohols

 Its manufactured on a large scale by
2 main processes:
– From sugars and starch by fermentation
– From petroleum fractions by hydration
Making ethanol by fermentation
 Yeast is added to sugar or starch.
 Left in a warm place for several days in the
absence of air.
 The fermentation process in anaerobic
which means it takes place in the absence
of oxygen.
 Yeast releases biological enzymes.
 These enzymes break down the sugars and
starches into glucose, C6H12O6.
 In the fermentation process, the enzyme
(zymase) slowly decomposes the glucose
to form ethanol and carbon dioxide.
Making ethanol by fermentation
 C6H12O6(aq) 2CH3CH2OH(aq) + 2CO2(g)
glucose ethanol Carbon dioxide

 Temperature : 18-200C
 Catalyst : yeast (zymase)
 Other condition : absence of oxygen

 When the concentration of ethanol formed

reaches about 15%, the yeast dies and the
fermentation stops.
 It is impossible to produce pure ethanol by
natural fermentation.
 The ethanol is then purified by fractional
distillation.
 Making ethanol by hydration
 An addition reaction combines ethene with
water to produce ethanol in the presence of
phosphoric acid as catalyst.
 Ethene is obtained from the cracking of
petroleum fractions.
 CH2=CH2(g) + H2O(g) CH3CH2OH(g)
ethene steam ethanol
 Temperature : 3000C
 Pressure : 60 atm
 Catalyst : phosphoric acid, H3PO4
 The ethanol produced is condensed to form
a liquid and the unreacted ethene is
recycled.
 Laboratory preparation of
ethanol
 All you need is some ripen fruits or
starchy foods and yeast.
 The yeast will convert the glucose to
ethanol.
 Laboratory work 2.3 page 38.
Physical properties of alcohols
Name Structural formula Boiling Solubility (g per
point (0C) 100cm3 water)

Methanol 65 Miscible in all

proportions

Ethanol 78 Miscible in all

proportions

Propanol 97 Miscible in all

proportions

Butanol 118 8.0

Pentanol 138 2.7

Physical properties of alcohols

 Notice that none of the alcohols

exists as a gas at room temperature
and pressure.
 Unlike alkanes or alkenes, simple
alcohols are very soluble in water.
 They have infinite solubility in water.
 Physical properties of
alcohols
Physical state at
room conditions
Boiling point
LOW BOILING POINT
LIQUID
Smell
(780C)
SHARP

Volatility ETHANOL Colour

VOLATILE COLOURLESS

Solubility in water
VERY SOLUBLE IN WATER.
MISCIBLE WITH WATER IN
ALL PROPORTIONS
Chemical properties of
ethanol

 Combustion
 Oxidation
 Dehydration
 Combustion
 Alcohols- very flammable substances
 Readily undergo combustion
 Ethanol burns with non-smoky blue flame
 Complete combustion of ethanol produces
carbon dioxide and water.
 C2H5OH(l) + 3O2(g) 2CO2(g) + 3H2O(l)
 Also releases lots of heat – suitable for use
as a fuel. Clean fuel because it does not
release pollutants into the atmosphere.
 Oxidation

 When a substance combines with oxygen

 Oxidizing agents are needed.
– Example :
• acidified potassium dichromate (VI),
K2Cr2O7 solution and
• acidified potassium manganate (VII),
KMnO4 solution
 Oxidation
 Form carboxylic acids – COOH group.
 When K2Cr2O7 solution is added to
ethanol and the mixture is warmed, it
turns form orange to green.

 CH3CH2OH(l) + 2[O] CH3COOH(l) +

ethanol ethanoic acid H2O(l)

 If KMnO4 solution is used instead, it

changes colour from purple to
colourless.
 Dehydration

 The removal of water from a

compound.
 In the dehydration of alcohols, a
molecule of water is eliminated from
each alcohol molecule.
 The alcohol molecule becomes an
alkene molecule.
 Dehydration
 The dehydration of ethanol produces
ethene.
 HH H H
 H-C-C-H H-C=C-H + H-OH
 H OH
ethanol ethene water

 The ethene produced can be detected by the

following tests:
– Decolourizes reddish-brown bromine water
– Decolourizes purple acidified KMnO4 solution
 Dehydration
 2 methods to carry out the
dehydration of ethanol in school
laboratory.
– Ethanol vapour is passed over a heated
catalyst such as unglazed porcelain
chips, porous pot, pumice stone or
aluminium oxide.
– Ethanol is heated under reflux at 1700C
with excess concentrated sulphuric
acid.
 Chemical properties of alcohols

Name Product

Combustion Oxidation Dehydration

Ethanol Carbon dioxide and Ethanoic acid and Ethene and water
water water

Methanol

Propanol

Butanol
 Chemical reactions of alcohols
Reactions Name Formula Chemical equation

Combustion Ethanol C2H5OH C2H5OH(ce) + 3O2(g) 2CO2(g) + 3H2O(ce)

Methanol

Propanol

Butanol

Oxidation Ethanol

Methanol

Propanol

Butanol

Dehydration Ethanol

Propanol

Butanol
 Uses of alcohols
 As a solvent in perfumes, cosmetics and
toiletries.
 As a thinner in lacquer, varnish, shellac
and ink.
 As a cleaner for a compac disc and video
cassette recorder head.
 As a fuel – clean fuel, biofuel, gasohol
 As a raw material in the manufacture of
vinegar, fibre, explosive and plastic.
 As a raw material to make pharmaceutical
products- tincture, antiseptic, cough
syrup, rubbing alcohol.
 Alcohol-misuse and abuse
 Ethanol – toxic
– Found in alcoholic drinks
– Act as depressant on the central
nervous system. It slows down both
physical and mental activity.Causes the
person to feel high and to lose all
shyness.
 Addictive.
 Cause chronic liver disease and
brain damage.
WORKSHEET 4
 a) HHH
H-C-C-C-OH
HHH

 b) X : acidified potassium manganate (VII)

solution / acidified potassium dichromate
(VI) solution
 Y : unglazed porcelain chips/porous
pot/pumice stone/aluminum oxide
 Q : propene
 W : Oxidation
 c) reaction W :
C3H7OH + 2[O]  C2H5COOH + H2O
 Dehydration :
C3H7OH  C3H6 + H2O
 Addition of hydroxyl group :
C3H6 + H2O  CH3CHCH2
OHOH