10 - Organic Chemistry

Contents
10.1 The unique properties of carbon
10.2 Alkanes
10.3 Alkenes
10.4 Hydrocarbon structure and isomerism
10.5 Chemical reactions of the alkanes
10.6 Chemical reactions of the alkenes
Contents
10.7 Alcohols
10.8 The reactions of ethanol
10.9 Organic acids and esters
10.1 The unique properties of carbon
10.1.1 Unique properties of carbon
10.1.2 Textbook questions
10.1.1 Unique properties of carbon
• Organic chemistry: chemistry of molecules including carbon atoms
• Three features of covalent bonding involving carbon:
• Carbon atoms can join to each other to form long chains – atoms
of other elements can then attach to the chain
• The carbon atoms in a chain can be linked by single, double or
triple covalent bonds
• Carbon atoms can also arrange themselves in rings
10.1.1 Unique properties of carbon
10.1.2 Textbook questions
10.2 Alkanes
10.2.1 What is a hydrocarbon?
10.2.2 Alkanes
10.2.3 Burning alkanes
10.2.4 Homologous series
10.2.5 Textbook questions
10.2.6 Past paper questions
10.2.1 What is a hydrocarbon?
• Hydrocarbon: a compound that contains carbon and hydrogen only
10.2.2 Alkanes
• Alkanes: saturated hydrocarbons; alkanes contain only single bonds
between carbon atoms; general molecular formula of CnH2n+2

• Structural formula: shows all the atoms and bonds in the molecule
10.2.2 Alkanes
10.2.2 Alkanes
10.2.3 Burning alkanes
• All alkanes burn very exothermically – good fuels
CH4(g) + 2O2 ⟶ CO2(g) + 2H2O(g)

• Propane and butane are sold as liquefied petroleum gas (LPG)

10.2.4 Homologous series
• Homologous series: a family of organic compounds that:
• Have the same general formula
• Have similar chemical properties
• Show a gradual increase in physical properties such as melting and
boiling point
10.2.5 Textbook questions
10.2.5 Textbook questions
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10.2.6 Past paper questions
• Jun 2015 qp11
10.2.6 Past paper questions
• Jun 2016 qp22
10.3 Alkenes
10.3.1 Alkenes
10.3.2 Chemical tests for unsaturation
10.3.3 Textbook questions
10.3.4 Past paper questions
10.3.1 Alkenes
• Unsaturated hydrocarbons
• Alkenes contain a C=C double bond in the chain
• General formula of CnH2n
10.3.1 Alkenes
• Alkenes give carbon dioxide and water vapour when burnt in oxygen
C2H4(g) + 3O2 ⟶ 2CO2(g) + 2H2O(g)

• The C=C double bond in an alkene makes it much more reactive than
alkanes; other atoms can add on to alkene molecules when the
double bond breaks open
• Functional group of alkenes: C=C bond – gives the homologous series
its characteristic properties
10.3.2 Chemical tests for unsaturation
• If alkene is shaken with a solution of
bromine in water, the bromine loses its
colour
C2H4(g) + Br2(aq) ⟶ C2H4Br2(l)
• The double bond in ethene breaks open
and forms new bonds to the bromine
atoms – addition reaction
• Similar reaction occurs between alkene
and an acidified dilute solution of
potassium permanganate(VII)
10.3.3 Textbook questions
10.3.3 Textbook questions
10.3.4 Past paper questions
• Jun 2015 qp13
10.4 Hydrocarbon structure and isomerism
10.4.1 Naming organic compounds
10.4.2 Isomerism
10.4.3 Textbook questions
10.4.4 Past paper questions
10.4.1 Naming organic compounds
• Prefixes: indicate the number of
carbon atoms in the chain
• Different homologous series have
particular ending to their names
10.4.2 Isomerism
• Molecules with the
same molecular
formula can have
different structures –
isomerism
• Isomers: compounds
that have the same
molecular formula but
different structural
formulae
10.4.3 Textbook questions
10.4.3 Textbook questions
10.4.3 Textbook questions
10.4.3 Textbook questions
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10.4.4 Past paper questions
• June 2015 qp12
10.5 Chemical reactions of the alkanes
10.5.1 Combustion
10.5.2 Substitution reactions with the halogens
10.5.3 Textbook questions
10.5.1 Combustion
• Complete combustion: requires sufficient air
2C4H10(g) + 13O2(g) ⟶ 8CO2(g) + 10H2O(g)
• Incomplete combustion: lack of air
2CH4(g) + 3O2(g) ⟶ 2CO(g) + 4H2O(g)
• Carbon monoxide: toxic as it interferes with the transport of oxygen
by red blood cells
• Incomplete combustion can also produce fine particles of carbon –
makes flame yellow
10.5.2 Substitution reactions with the
halogens
• Substitution reaction with chlorine is a photochemical reaction
CH4(g) + Cl2(g) ⟶ CH3Cl(g) + HCl(g)
• Requires ultraviolet radiation for the reaction to take place
• Reaction can continue further to produce CH2Cl2, CHCl3 and CCl4
• Substituted alkanes are also good organic solvents
10.5.3 Textbook questions
10.5.3 Textbook questions
10.5.3 Textbook questions
10.5.3 Textbook questions
10.6 Chemical reactions of the alkenes
10.6.1 Bromination
10.6.2 Hydrogenation
10.6.3 Hydration
10.6.4 Textbook questions
10.6.1 Bromination
• Used as a chemical test for an unsaturated hydrocarbon
C2H4(g) + Br2(aq) ⟶ C2H4Br2(l)
• Can also work with bromine dissolved in an organic solvent (e.g.
hexane)
10.6.2 Hydrogenation
• Addition of hydrogen across a C=C double bond
• Ethene reacts with hydrogen if the heated gases are passed over a
catalyst
C2H4(g) + H2(aq) ⟶ C2H6(l)
• Hydrogenation reactions are used in the manufacture of margarine
from vegetable oils – the C=C double bonds are saturated to make
margarine
10.6.3 Hydration
• Used in the manufacture of ethanol
C2H4(g) + H2O(g) ⟶ C2H5OH(g)
• Mixture of steam and ethene is passed over a catalyst of immobilized
phosphoric(V) acid at 300°C and 60atm
10.6.4 Textbook questions
10.6.4 Textbook questions
10.6.4 Textbook questions
10.7 Alcohols
10.7.1 Alcohols
10.7.2 Making ethanol
10.7.3 Textbook questions
10.7.4 Past paper questions
10.7.1 Alcohols
• Alcohol: series of organic
compounds with the functional
group -OH
• General formula: CnH2n+1OH
10.7.2 Making ethanol
• Hydration of ethene (300°C, 60atm, phosphoric acid)
ethene + steam ⟶ ethanol
C2H4(g) + H2O(g) ⟶ C2H5OH(g)
• Fermentation – ferment sugar to gain energy by anaerobic respiration
(yeast)
glucose ⟶ ethanol + carbon dioxide
C6H12O6(aq) ⟶ 2C2H5OH(aq) + 2CO2(g)
10.7.2 Making ethanol
10.7.3 Textbook questions
10.7.3 Textbook questions
10.7.3 Textbook questions
10.7.4 Past paper questions
• Jun 2016 qp21
10.8 The reactions of ethanol
10.8.1 Ethanol as a fuel
10.8.2 Oxidation
10.8.3 Dehydration
10.8.4 Esterification
10.8.5 Alcohol and health
10.8.6 Textbook questions
10.8.7 Past paper questions
10.8.1 Ethanol as a fuel
• Ethanol burns with a clear flame, giving out a lot of heat
ethanol + oxygen ⟶ carbon dioxide + water
C2H5OH(l) + 3O2(g) ⟶ 2CO2(g) + 3H2O(g)
10.8.2 Oxidation
• Vinegar: weak solution of ethanoic acid(acetic acid)
• Produced commercially from wine by biochemical oxidation using
bacteria (Acetobacter); same can be done by using powerful oxidizing
agents such as warm acidified potassium permanganate
ethanol + oxygen ⟶ ethanoic acid + water
C2H5OH + 2[O] ⟶ CH3COOH + H2O
10.8.3 Dehydration
• Ethanol can be dehydrated to produce ethene
• Ethanol vapour passed over heated catalyst (aluminium oxide or
broken pieces of porous pot)
10.8.4 Esterification
• Alcohols react with organic acids to form sweet-smelling oily liquids
known as esters
• Concentrated sulfuric acid used as catalyst
ethanoic acid + ethanol ⟶ ethyl ethanoate + water
CH3COOH(l) + C2H5OH(l) ⟶ CH3COOC2H5(l) + H2O(l)
10.8.5 Alcohol and health
• Ethanol: only alcohol that is safe to drink; must be drunk in
moderation
• Methanol: very toxic and small amounts can cause blindness and
death

• Ethanol is very soluble in water which takes it around the body;

prolonged heavy drinking can damage the muscle tissue of heart,
brain, and liver failure
10.8.6 Textbook questions
10.8.6 Textbook questions
10.8.6 Textbook questions
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10.8.7 Past paper questions
• Jun 2015 qp11
10.9 Organic acids and esters
10.9.1 Carboxylic acids
10.9.2 Ethanoic acid as a weak acid
10.9.3 Esterification
10.9.4 Textbook questions
10.9.5 Past paper questions
10.9.1 Carboxylic acids
• Carboxylic acids: organic compounds with
the functional group -COOH
• General formula: CnH2n+1COOH
10.9.2 Ethanoic acid as a weak acid
• Ethanoic acid partially dissociates in water; dynamic equilibrium
made
ethanoic acid ⇄ ethanoate ions + hydrogen ions
CH3COOH(aq) ⇄ CH3COO-(aq) + H+(aq)
• Vinegar can be used as a descaler in hard water areas
calcium carbonate + ethanoic acid ⟶
calcium ethanoate + water + carbon dioxide
CaCO3(s) + 2CH3COOH(aq) ⟶ (CH3COO)2Ca(aq) + H2O(l) + CO2(g)
10.9.3 Esterification
• Ethanoic acid reacts with ethanol
in the presence of few drops of
concentrated sulfuric acid to
produce ethyl ethanoate
ethanoic acid + ethanol ⟶ ethyl
ethanoate + water
CH3COOH(l) + C2H5OH(l) ⟶
CH3COOC2H5(l) + H2O(l)
10.9.4 Textbook questions
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10.9.4 Textbook questions
10.9.5 Past paper questions
• Jun 2015 qp11
10.9.5 Past paper questions
• Jun 2015 qp12