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11.6Organic Chemistry

Alcohols — Cambridge IGCSE Chemistry 0620 Revision Notes & Topical Questions

5 min read 11 parts Lesson 6 of 10 Unit quiz

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11.6 Alcohols — Notes — IGCSE Chemistry notes: Describe the alcohol homologous series, the manufacture of ethanol and its combustion and uses.Functional group — the hydroxyl group, –OH, is responsible for the characteristic reactions.- General formula — CnH2n+1OH, and members dif…

  • Renewable fuel
  • Energy released
  • Disinfectant
  • Other uses
  • Lower alcohols
  • Boiling point

Part 1 of 9The alcohols

The alcohols
Functional group
  • Functional group the hydroxyl group, –OH, is responsible for the characteristic reactions.
- General formula
  • CnH2n+1OH, and members differ by –CH2–.
NameFormula
MethanolCH3OH
EthanolC2H5OH (CH3CH2OH)
PropanolC3H7OH
Naming
  • Naming name the alcohol from the number of carbon atoms and the –OH group.
Ethanol
  • Ethanol it is colourless, volatile and flammable, and it mixes with water.
It boils at 78 °C, higher than ethane, because of hydrogen bonding between its molecules.

Part 2 of 9Combustion and uses of ethanol

Combustion and uses of ethanol
Combustion
  • Combustion ethanol burns in excess oxygen to give carbon dioxide and water, C2H5OH + 3O2 → 2CO2 + 3H2O.
Uses
  • Uses a solvent and a fuel, including as a fuel for cars.
Drinks
  • Drinks it is the alcohol found in wine and beer.
Renewable fuel
  • Renewable fuel ethanol from fermentation is a renewable biofuel.
Flame
  • Flame alcohols burn with a pale blue flame, so ethanol is useful in spirit burners or mixed with petrol.
Energy released
  • Energy released the energy released per mole increases with chain length.
Solvent
  • Solvent ethanol is used in perfumes, cosmetics, paints and medicines.
Disinfectant
  • Disinfectant ethanol and propan-2-ol kill microbes and evaporate quickly.
Other uses
  • Other uses methanol is a chemical feedstock and is used in antifreeze.
Safety
  • Safety excess ethanol damages the liver and judgement, and methanol is toxic.
Growing crops for bioethanol competes with food production.

Part 3 of 9Physical properties of alcohols

Lower alcohols
  • Lower alcohols methanol, ethanol and propanol are colourless liquids that mix completely with water.
Boiling point
  • Boiling point it rises with chain length: methanol 65 °C, ethanol 78 °C, propan-1-ol 97 °C and butan-1-ol 118 °C.
  • It is higher than for alkanes of similar mass because of hydrogen bonding.
Solubility
  • Solubility it decreases as the hydrocarbon chain gets longer.
Hazard
  • Hazard alcohols are flammable and volatile.

Part 4 of 9Hydration of ethene

1
A mixture of ethene and steam is passed over a hot catalyst of phosphoric acid.
2
The temperature is about 300 °C and the pressure is 60 atmospheres (6000 kPa).
3
The gaseous ethanol is condensed into a liquid.
4Equation
  • C2H4 + H2O → C2H5OH.
5Reversible
  • Reversible the reaction is reversible, so unreacted ethene is recycled to increase the yield.
6Source of ethene
  • Source of ethene cracking of oil fractions.

Part 5 of 9Fermentation of glucose

1
Conditions
  • Conditions aqueous glucose with yeast at 25–35 °C in the absence of oxygen for a few days.
2
Role of yeast
  • Role of yeast yeast contains enzymes that catalyse the breakdown of sugar, respiring anaerobically.
3
Equation
  • C6H12O6 → 2C2H5OH + 2CO2.
4
Temperature
  • Temperature too low gives a rate that is too slow and too high denatures the enzymes.
5
Batch process
  • Batch process the yeast is killed when the alcohol concentration reaches about 15%, so the vessel is emptied and the process restarted.
6
Dissolve sugar or starch in water and add yeast, whose enzymes break starch or sugar down to glucose.
7
An airlock lets the carbon dioxide escape while keeping oxygen out.
8
Concentration
  • Concentration fractional distillation of the dilute product gives a more concentrated ethanol.

Part 6 of 9Comparing the methods (Extended)

FeatureHydration of etheneFermentation
EquipmentComplexSimple
Raw materialsNon-renewable (crude oil)Renewable (sugar cane)
Type of processContinuousBatch
RateFastVery slow (several days)
Quality of productPure ethanolDilute solution needing further processing
Atmospheric effectsNo greenhouse gases made directly, but fossil fuels are burned for heatCarbon dioxide is produced
ConditionsHigh temperature and pressure, so higher energy costLow temperature
Atom economy100%, one productLower, because carbon dioxide is a by-product

Part 7 of 9Making ethanoic acid from ethanol

Oxidation
  • Oxidation ethanol can be oxidised to ethanoic acid.
Reaction with acid
  • Reaction with acid alcohols react with carboxylic acids to form esters.
Oxidising agents
  • Oxidising agents ethanol is heated with acidified potassium manganate(VII) or acidified potassium dichromate(VI) (orange to green),
    • and the colour change shows oxidation has occurred.
    • (purple to colourless)
Microbes in air oxidise the ethanol in wine to ethanoic acid, so wine turns to vinegar.

Part 8 of 9Other reactions of alcohols

With carboxylic acids
  • With carboxylic acids a concentrated sulfuric acid catalyst gives an ester and water.
With sodium
  • With sodium it gives hydrogen and sodium ethoxide, more slowly than water: 2C2H5OH + 2Na → 2C2H5ONa + H2.
Dehydration
  • Dehydration ethanol passed over hot aluminium oxide gives ethene and water.
Oxidation equation
  • C2H5OH + 2[O] → CH3COOH + H2O.

Part 9 of 9More from the specification

1Industrial Production Methods of Ethanol
  • Ethanol is synthesized either through the catalytic hydration of ethene with steam or by yeast fermentation of aqueous glucose at 30–35 °C in anaerobic conditions (batch process using renewable plant starch).
    • (fast, continuous, high purity)
2Complete Combustion of Alcohols
  • Alcohols burn cleanly with a blue flame in oxygen to produce carbon dioxide and water: C2H5OH + 3O2 → 2CO2 + 3H2O,
    • making them viable renewable biofuels.
3Controlled Oxidation to Carboxylic Acids
  • Warming ethanol with acidified potassium manganate(VII) or acidified potassium dichromate(VI) oxidises the terminal hydroxyl group to form ethanoic acid (CH3COOH).
4Covalent bond
  • A shared pair of electrons between two atoms, giving noble gas configurations.
5Substitution reaction
  • A reaction in which one atom or group is replaced by another.
6Ultraviolet radiation
  • Radiation that provides the activation energy for alkane–halogen reactions.
7Alkene
  • A hydrocarbon with a C=C bond and a name ending in -ene.
8Bromine water
  • An orange solution that is decolourised by alkenes.
9Addition reaction
  • A reaction in which atoms add across a C=C bond to give one product.
10Displayed formula
  • A formula showing all atoms and all bonds.

Key terms

TermMeaning
AlcoholCompound containing the –OH functional group.
FermentationGlucose to ethanol and CO2 using yeast at 25–35 °C without oxygen.
HydrationAddition of steam to ethene to make ethanol.
Batch processEverything is mixed in a vessel, left, and the process repeated.
Continuous processReactants are constantly passed over a catalyst.
Hydroxyl groupthe –OH functional group of alcohols.
Oxidising agenta substance that supplies oxygen, shown as [O].
Hydrogen bondinga strong attraction between molecules containing –OH groups.

Avoid these mistakes

1
Mixing up the conditions — hydration uses steam, 300 °C, 60 atm and an acid catalyst, and fermentation uses yeast at 25–35 °C without oxygen.
2
Saying fermentation needs oxygen — it is anaerobic.
3
Saying fermentation is continuous — it is a batch process.
4
Saying the –OH in alcohols makes them alkalis — alcohols are not alkaline.
5
Saying ethanol is oxidised to ethane — it is oxidised to ethanoic acid

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