ALCOHOLS

The Alcohols
 In terms of naming, the same system is used as for alkanes and alkenes, with the final ‘e’ being
replaced with ‘ol’

Oxidation of Ethanol
 Ethanol can undergo oxidation in three different ways: 
o Combustion
o Aerobic oxidation
o Treatment with an oxidising agent

Combustion
 Alcohols undergo combustion to form carbon dioxide and water
 The complete combustion of ethanol is as follows:

 Ethanol burns readily with an almost invisible blue flame

Aerobic Oxidation
 Bacteria in the air (acetobacter) use atmospheric oxygen from air to oxidise the ethanol in the
wine:
ethanol + oxygen → ethanoic acid + water
 The acidic, vinegary taste of wine which has been left open for several days is due to the
presence of ethanoic acid
  This is what happens to wine when it is left open as the microbial oxidation of ethanol will
produce a weak solution of the carboxylic acid, ethanoic acid, the same acid used in vinegar

Treatment with an oxidising agent

 Alcohols undergo oxidation to produce carboxylic acids when treated with oxidising agents
 When ethanol is heated with acidified potassium dichromate solution the ethanol oxidises to
ethanoic acid
 The equation for the reaction is:
CH3CH2OH + [O]  →  CH3COOH + H2O
 During the reaction the potassium dichromate turns from orange to green

Industrial Synthesis of Ethanol

 Ethanol can be synthesised by the hydration of ethene
 The hydration reaction is very important industrially for the production of alcohols and it occurs
using the following conditions: 
o Temperature of around 330ºC
o Pressure of 60 – 70 atm
o Concentrated phosphoric acid catalyst
 When the reaction is complete, the reaction chamber holds unreacted ethene, ethanol and
water
 The contents are transferred to a condenser where ethene is separated easily as it has a much
lower boiling point than ethanol and water: 
o Ethanol: 78oC
o Ethene: -103oC
o Water: 100oC
 The ethanol and water are separated afterwards by fractional distillation
Fermentation
 It can be produced by fermentation where sugar or starch is dissolved in water and yeast is
added
 The mixture is then fermented between 15 and 35°C with the absence of oxygen for a few days
 Yeast contains enzymes that break down sugar to alcohol
 If the temperature is too low the reaction rate will be too slow and if it is too high the enzymes
will become denatured
 The yeast respires anaerobically using the glucose to form ethanol and carbon dioxide:
C6H12O6 + enzymes → 2CO2 + 2C2H5OH
 The yeast is killed off once the concentration of alcohol reaches around 15%, hence the reaction
vessel is emptied and the process is started again
 This is the reason that ethanol production by fermentation is a batch process