The World of Carbon

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Unit 2

• The World of Carbon

2
Menu

• Fuels
• Nomenclature
• Reactions of Carbon Compounds
• Polymers
• Natural Products

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Fuels
4
Crude oil

• Crude oil is a source of many fuels.
• It is also the principal feedstock for the
  manufacture of petroleum-based consumer products
  because these are compounds of carbon.

5
Petrol

• Petrol can be produced by the reforming of
  naphtha.
• Reforming alters the arrangement of atoms in
  molecules without necessarily changing the number
  of carbon atoms per molecule.

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• As a result of the reforming process, petrol
  contains branched-chain alkanes, cycloalkanes and
  aromatic hydrocarbons as well as straight-chain
  alkanes.

7

• Any petrol is a blend of hydrocarbons which boil
  at different temperatures.
• A winter blend of petrol is different from a
  summer blend. In winter butane is added to
  petrol so that it will catch fire more easily.

8
Engines

• In a petrol engine, the petrol-air mixture is
  ignited by a spark.
• Knocking is caused by auto-ignition.
• Auto-ignition is when the petrol-air mix ignites
  too soon due to the heat from the engine. This
  makes the engine perform badly.
• Knocking is when the engine shakes and shudders.

9

• The tendency of alkanes to auto-ignite used to be
  reduced by the addition of lead compounds.
• Unfortunately the lead compounds cause serious
  environmental problems.

10

• Unleaded petrol uses components which have a high
  degree of molecular branching and/or aromatics
  and/or cycloalkanes to improve the efficiency of
  burning.

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Alternative fuels

• Fossil fuels are going to run out in the future.
• Fuels used produce carbon dioxide, which
  increases the greenhouse effect.
• We need other fuels which are renewable and
  non-polluting.

12

• Sugar cane is a renewable source of ethanol for
  mixing with petrol.
• Some biological materials,(i.e. manure and straw)
  under anaerobic conditions, ferment to produce
  methane (biogas).
• Methanol is an alternative fuel to petrol, but it
  has certain disadvantages, as well as advantages.

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Methanol

• Almost complete combustion
• No carcinogens
• Cheaper than petrol
• Less explosive than petrol
• Little modification to car engine

• Difficult to mix with petrol
• Very corrosive
• Toxic
• Larger fuel tanks needed.

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• Hydrogen could well be the fuel of the future.
• If water can be electrolysed, using a renewable
  energy source, such as solar power, hydrogen will
  be obtained.
• The hydrogen will burn, producing water, and so
  will be pollution-free.
• The problem with hydrogen is storing the gas in
  large enough quantities.

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Fuels

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Nomenclature Structural formula
17
Nomenclature

• Nomenclature means the way chemical compounds are
  given names.
• These names are produced by a special system.

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Naming organic compounds

• All organic compounds belong to families called
  homologous series.
• A homologous series is a set of compounds with
  the same general formula, similar chemical
  properties and graded physical properties.

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• Most homologous series have a special functional
  group.
• A functional group is a reactive group of atoms
  which are attached to the carbon chain.
• The functional group is the part of the molecule
  where most reactions take place.

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Functional Groups
Functional Group Name of Group Homologous series
none Alkanes
Double bond Alkenes
Triple bond Alkynes
Hydroxyl Alkanols (Alcohols)
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Functional Groups
Functional Group Name of Group Homologous series
Carbonyl Alkanals (Aldehydes)
Carbonyl Alkanones (Ketones)
Carboxylic Alkanoic acids
Amine Amines
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• The first part of the compounds name is decided
  by the number of carbon atoms in the molecule.
• The second part of the name is decided by the
  homologous series to which the compound belongs.

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Number of C atoms First part of name Number of C atoms First part of name
1 meth- 5 pent-
2 eth- 6 hex-
3 prop- 7 hept-
4 but- 8 oct-
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2nd Part of Name
Homologous series General Formula Name ending
Alkanes CnH 2n2 ane
Alkenes CnH 2n ene
Alkynes CnH 2n-2 yne
Alkanols CnH 2n1OH anol
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2nd Part of Name
Homologous series General Formula Name ending
Alkanals CnH 2n2 anal
Alkanones CnH 2n anone
Alkanoic acids CnH 2n-2 anoic acid
Amines CnH 2n1OH ylamine
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• This method works well for straight-chain
  hydrocarbons.
• Here is an example hexane

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• We have to add rules to help deal with branched
  chains.

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• First draw out the full structure.

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• Number the atoms in the longest continuous carbon
  chain.
• Start at the end nearer most groups.

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• This now gives us the basic name in this case
  hexane.

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• You must now identify any side chains.
• -CH3 is methyl
• -CH2CH3 is ethyl

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• Now identify and count the number and type of
  side chain.
• di - shows 2
• tri shows 3
• tetra shows 4
• Label the carbon atom(s) they join

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• This now gives us the full name
• 2,2,4 trimethylhexane.

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• Naming other homologous series works in the same
  way.
• With those we start numbering at the end nearer
  the functional group e.g. this alkene

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• Number the atoms in the longest carbon chain.

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• This now gives us the basic name in this case
  hex-2-ene.

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• Identifying the side chains gives us the full
  name
• 5,5 dimethy 4 ethyl hex-2-ene.

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• We can use the same principles with cyclic
  hydrocarbons.

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• 1 methyl cyclopentane

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Isomers

•  Isomers are compounds with the same molecular
  formula but different structural formulae
• For example C4H10

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Alcohols

• The alcohols form another homologous series
  called the alkanols.
• We can recognise the alkanols because they
  contain an OH group.
• They are given names as if they are substituted
  alkanes.

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• 3 methyl pentan-2-ol

43
Aldehydes

• The aldehydes form another homologous series
  called the alkanals.
• We can recognise the alkanals because they
  contain a carbonyl group at the end of the carbon
  chain.
• They are named as if they are substituted alkanes.

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• 3,4 dimethyl pentanal
• We dont need to number the carbonyl group
  because it must be on the first carbon.

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Ketones

• The ketones form another homologous series
  called the alkanones.
• We can recognise the alkanones because they
  contain a carbonyl group in the middle of the
  carbon chain.
• They are named as if they are substituted alkanes.

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• 3,3 dimethyl pentan-2-one

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Alkanoic acids

• The alkanoic acids form another homologous
  series.
•  
• Carboxylic acids are used in a variety of ways.

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Alkanoic acids

• We can recognise the alkanoic acids because they
  contain a COOH group.

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• We can name the alkanoic acids using the
  principles we have used before.

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• 4 methyl hexanoic acid
• We dont need to number the acid group because it
  must be on the first carbon.

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Esters

• An ester can be identified the -oate
  ending to its name.
• The ester group is

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Esters

• An ester can be named given the names of the
  parent alkanol and alkanoic acid.
• The name also tells us the alkanoic acid and
  alkanol that are made when the ester is broken
  down.

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The acid and alkanol combine
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The acid and alkanol combine
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The acid and alkanol combine
Water is formed.
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H2O
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Naming esters
Acid name Alkanol name Ester name
ethanoic acid methanol methyl ethanoate
propanoic acid ethanol ethyl propanoate
butanoic acid propanol propyl butanoate
methanoic acid butanol butyl methanoate
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• A typical ester is shown below.

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• We can identify the part that came from the
  alkanoic acid propanoic acid.

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• We can identify the part that came from the
  alkanol - ethanol

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• This gives us the name
• ethyl propanoate

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Aromatic Hydrocarbons

• Benzene is the simplest aromatic hydrocarbon.
• It has the formula C6H6.
• The benzene molecule has a ring structure.

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• Even though benzene would seem to be unsaturated
  it does not decolourise bromine water.
• All the bonds in benzene are equivalent to each
  other it does not have the usual kind of single
  and double bonds.

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• The bonds in benzene are intermediate between
  single and double bonds.
• Their lengths and bond energies are in between
  those of single and double bonds.

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• The stability of the benzene ring is due to the
  delocalisation of electrons.
• A benzene ring in which one hydrogen atom has
  been substituted by another group is known as the
  phenyl group.
• The phenyl group has the formula -C6H5.

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Benzene and its related compounds are important
as feedstocks. One or more hydrogen atoms of a
benzene molecule can be substituted to form a
range of consumer products.
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Nomenclature and Structural Formula

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  Formula
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Reactions of Carbon Compounds
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Saturated Hydrocarbons

• Alkanes and cycloalkanes are saturated
  hydrocarbons.
• Saturated hydrocarbons contain only carbon to
  carbon single covalent bonds.

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Unsaturated Hydrocarbons

• The alkenes are unsaturated hydrocarbons.
• Unsaturated hydrocarbons contain at least one
  carbon to carbon double covalent bond.

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Addition Reactions

• Addition reactions take place when atoms, or
  groups of atoms, add across a carbon to carbon
  double bond or carbon to carbon triple bond.

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• For alkenes the basic reaction is

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• When bromine adds to an alkene we have an
  addition reaction.
• C4H8 Br2 ? C4H8 Br2

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• The addition reaction between hydrogen chlkoride
  and an alkene gives the equivalent alkyl
  chloride.
• C3H6 HCl ? C3H7Cl

propene hydrogen chloride ? propyl chloride
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Halogenoalkanes

• Halogenoalkanes have properties which make them
  useful in a variety of consumer products.
• In the atmosphere, ozone, O3, forms a protective
  layer which absorbs ultraviolet radiation from
  the sun.
• The depletion of the ozone layer is believed to
  have been caused by the extensive use of certain
  CFCs (chlorofluorocarbons).

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• The addition reaction between water and an alkene
  gives the equivalent alkanol.
• propene water ? propanol
• C3H6 H2O ? C3H7OH

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Sometimes addition reactions can give two
different isomeric products.
CH2CH-CH3
CH2Cl-CH2-CH3
CH3-CHCl-CH3
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Ethanol

• To meet market demand ethanol is made by means
  other than fermentation.
• Industrial ethanol is manufactured by the
  catalytic hydration of ethene.

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• Ethanol can be converted to ethene by
  dehydration.
• This reaction uses aluminium oxide or
  concentrated sulphuric acid as a catalyst.

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• For alkynes the reaction takes place in two
  stages

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With hydrogen
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With a halogen
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With a halogen halide
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The benzene ring resists any addition reactions.
Its delocalised electrons mean that its bonds do
not behave like the bonds in an unsaturated
compound
86
Alcohols

• There are three types of alcohols
• Primary
• Secondary
• Tertiary

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Primary Alcohols

• Primary alcohols have at least two hydrogen atoms
  on the carbon atom carrying the OH group.

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Secondary Alcohols

• Secondary alcohols have one hydrogen atom on the
  carbon atom carrying the OH group.

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Tertiary Alcohols

• Tertiary alcohols have at no hydrogen atoms on
  the carbon atom carrying the OH group.

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Oxidation and Reduction

• Oxidation and reduction can be described in terms
  of loss or gain of electrons.
• In organic chemistry it is more useful to
  describe them differently.

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• Oxidation is an increase in the oxygen to
  hydrogen ratio e.g.
• CH3CH2OH ? CH3CHO
• 16 14
  
• Reduction is a decrease in the oxygen to
  hydrogen ratio.
• CH3CO2H ? CH3CH2OH
• 24 16

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Oxidation Reactions

• The simplest oxidation reaction of alcohols is
  when they are burned in oxygen, giving carbon
  dioxide and water.
• Some alcohols can be oxidised to give aldehydes
  and ketones.

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• Primary alcohols can be oxidised in two stages
  first to an aldehyde

Primary alcohol ? Aldehyde
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• Primary alcohols can be oxidised in two stages
  first to an aldehyde and then to an alkanoic acid.

Primary alcohol ? Aldehyde
Aldehyde ? Alkanoic
Acid
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• Secondary alcohols can be oxidised only once to
  a ketone

Secondary alcohol ? Ketone
No further oxidation is possible
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• Tertiary alcohols cannot be oxidised at all.

No oxidation is possible
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• Aldehydes can be oxidised to give carboxylic
  (alkanoic) acids while ketones cannot.
• This can be used as a means of differentiating
  between aldehydes and ketones.
• The oxidising agents that are used most often
  give visible signs of reaction.

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Reagent Visible effect
Acidified permanganate Purple ? colourless
Acidified dichromate Orange ? green
Copper oxide Black ? brown
Tollens Reagent Silver mirror produced
Fehlings solution Blue ? red
Benedicts solution Blue ? red
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Condensation Reactions

• In a condensation reaction, the molecules join
  together by the reaction of the functional groups
  to make water.

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Esters

• Esters are formed by the condensation reaction
  between a carboxylic acid and an alcohol.
• Uses of esters include flavourings, perfumes and
  solvents.

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Esters

• Esters can be recognised by the ester link shown
  below

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• The ester link is formed by the reaction of a
  hydroxyl group of an alkanol with a carboxyl
  group of a carboxylic acid.

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• The ester link is formed by the reaction of a
  hydroxyl group of an alkanol with a carboxyl
  group of a carboxylic acid.

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• The ester link is formed by the reaction of a
  hydroxyl group of an alkanol with a carboxyl
  group of a carboxylic acid.

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• The ester link is formed by the reaction of a
  hydroxyl group of an alkanol with a carboxyl
  group of a carboxylic acid.

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Water is formed from hydrogen of one molecule
and hydroxide from the other.
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H2O
Water is formed from hydrogen of one molecule
and hydroxide from the other.
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H2O
Water is formed from hydrogen of one molecule
and hydroxide from the other.
The remains of the molecules join together
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H2O
Water is formed from hydrogen of one molecule
and hydroxide from the other.
The remains of the molecules join together
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Hydrolysis Reactions

• In a hydrolysis reaction, a molecule is split up
  by adding the elements of water.

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• The carboxylic acid and the alcohol from which
  the ester are made can be obtained by hydrolysis.

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• The formation and hydrolysis of an ester is a
  reversible reaction.

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Yields

• If we write the equation for a reaction we can
  calculate what mass of product should be produced
  the theoretical yield.
• When we carry out the experiment we can measure
  the mass of product produced the actual yield.

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Percentage Yield

• Percentage yield is the actual yield, expressed
  as a percentage of the theoretical yield.

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Titanium dioxide, TiO2, is used in the
manufacture of white paint. It is made from
ilmenite, FeTiO3. If 45.1kg of TiO2 is obtained
from 100kg of ilmenite, what is the percentage
yield of the conversion?
FeTiO3 ? TiO2
1 mole ? 1 mole
152g ? 80g
1g ? 80/152g 0.5263g
100kg ? 52.63kg
Percentage yield 45.1 x 100 85.7
52.63 1

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Reactions of Carbon Compounds

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Polymers
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Addition Polymerisation

• Many polymers are made from the small unsaturated
  molecules, produced by the cracking of oil.
• They add to each other by opening up their carbon
  to carbon double bonds.
• This process is called addition polymerisation.

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• Ethene is a starting material of major importance
  in the petrochemical industry especially for the
  manufacture of plastics.
• It is formed by cracking the ethane from the gas
  fraction or the naphtha fraction from oil.
• Propene can be formed by cracking the propane
  from the gas fraction or the naphtha fraction
  from oil.

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I
The ethene is attacked by an initiator (I) which
opens up the double bond
124
The ethene is attacked by an initiator (I) which
opens up the double bond
Another ethene adds on.
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The ethene is attacked by an initiator (I) which
opens up the double bond
Then another
Another ethene adds on.
126
The ethene is attacked by an initiator (I) which
opens up the double bond
.
Then another
Another ethene adds on.
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Naming polymers

• The name of the polymer is derived from its
  monomer.
• MONOMER POLYMER
•  ene poly(ene)
• ethene poly(ethene)
• propene poly(propene)
• styrene poly(styrene)
• chloroethene poly(chloroethene)
• tetrafluoroethene poly(tetrafluoroethene)

128
Repeat Units

• You can look at the structure of an addition
  polymer and work out its repeat unit and the
  monomer from which it was formed.
• The repeat unit of an addition polymer is always
  only two carbon atoms long.

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-CH2 -CH2 -CH2 -CH2 -CH2 -CH2 -CH2 -CH2 -
-CH2 -CH2 -CH2 -CH2 -CH2 -CH2 -CH2 -CH2 -
Repeat Unit CH2 -CH2
Monomer CH2 CH2
-CH2 -CHCl -CH2 -CHCl -CH2 -CHCl -CH2 -CHCl -
-CH2 -CHCl -CH2 -CHCl -CH2 -CHCl -CH2 -CHCl -
Monomer CH2 CHCl
Repeat Unit CH2 -CHCl
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Condensation Polymers

• Condensation reactions involve eliminating water
  when two molecules join.
• Condensation polymers are made from monomers with
  two functional groups per molecule.

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• Normally there are two different monomers which
  alternate in the structure e.g.

and
132

• The molecules join together, eliminating water as
  they do so.
• Hydrogen comes from one molecule.
• Hydroxide comes from the other molecule.
• The molecules join where these groups have come
  off.

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H2O
H2O
H2O
H2O
H2O
139
Repeat Units

• You can look at the structure of a condensation
  polymer and work out its repeat unit and the
  monomers from which it was formed.

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Polymer
Repeat Unit
Monomers
and
141
Polymer
Repeat Unit
Monomers
HO-CH2-CH2 -OH
and
142
Condensation Polymers

• Typical condensation polymers are polyesters and
  polyamides.
• Terylene is the brand name for a typical
  polyester.

143
Polyesters

• As the name suggests polyesters are polymers
  which use the ester link.
• The two monomers which are used are a diacid and
  a diol.

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The diacid will have a typical structure
The diol will have a typical structure
They combine like this
145
The diacid will have a typical structure
The diol will have a typical structure
They combine like this
146
The diacid will have a typical structure
The diol will have a typical structure
They combine like this
147
The diacid will have a typical structure
The diol will have a typical structure
They combine like this
148
The diacid will have a typical structure
The diol will have a typical structure
They combine like this
149

• Polyesters are manufactured for use as textile
  fibres and resins.
• Polyesters used for textile fibres have a linear
  structure.
• Cured polyester resins have a three-dimensional
  structure. Cross linking between the polyester
  chains makes the structure much more rigid.

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Amines

• Amines are a homologous series containing the
  amine group

151
The amide link

• The amide link is formed when an acid and amine
  join together.

152
The amide link

• The amide link is formed when an acid and amine
  join together.

153
The amide link

• The amide link is formed when an acid and amine
  join together.

H2O
154
The amide link

• The amide link is formed when an acid and amine
  join together.

The amide link
155
Polyamides

• A polyamide is made from a diamine and a diacid

They combine like this
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• Nylon is a typical polyamide.
• Nylon is a very important engineering plastic.
• The strength of nylon is caused by hydrogen
  bonding between the polymer chains.

161
Synthesis gas

• Synthesis gas can be obtained by steam reforming
  of methane from natural gas.
• CH4 H2O ? CO 3H2
• It can also be made by the steam reforming of
  coal.

162

• Methanol, used in the production of methanal, is
  made industrially from synthesis gas.
• Methanal is an important feedstock in the
  manufacture of thermosetting plastics.
• It is used to assist cross-linking so as to make
  thermosetting plastics and resins.

163
New polymers

• Kevlar is an aromatic polyamide which is
  extremely strong because of the way in which the
  rigid, linear molecules are packed together.
• These molecules are held together by hydrogen
  bonds.
• Kevlar has many important uses.

164

• Poly(ethenol) is a plastic which readily
  dissolves in water. It has many important uses
• It is made from another plastic by a process
  known as ester exchange.
• The percentage of acid groups which have been
  removed in the production process affects the
  strengths of the intermolecular forces upon which
  the solubility depends.

165

• Poly(ethyne) can be treated to make a polymer
  which conducts electricity.
• The conductivity depends on delocalised electrons
  along the polymer chain.
• Poly(vinyl carbazole) is a polymer which exhibits
  photoconductivity and is used in photocopiers.

166

• Biopol is an example of a biodegradable polymer.
• The structure of low density polythene can be
  modified during manufacture to produce a
  photodegradable polymer.

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Polymers

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Natural Products
169
Fats and Oils

• Natural fats and oils can be classified according
  to where they come from
• Animal
• Vegetable
• Marine

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• Fats and oils in the diet supply the body with
  energy.
• They are a more concentrated source of energy
  than carbohydrates.
• Oils are liquids and fats are solids.
• Oils have lower melting points than fats.
• This is because oil molecules have a greater
  degree of unsaturation.

171
Saturated fats
have more regular shapes than unsaturated oils
172
Fat molecules close pack together easily and
have a low melting point
173
Oil molecules do not close pack together so
easily and have a high melting point
174
Oils can be converted into hardened fats by
adding of hydrogen.
H2
H2
H2
175
Oils can be converted into hardened fats by
adding of hydrogen.
This is how margarine is made
176
Fatty acids

• Fatty acids are straight chain carboxylic acids,
  containing even numbers of carbon atoms from C4
  to C24, primarily C16 and C18.
• Fatty acids may be saturated or unsaturated.

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• Fats and oils are esters.
• They are made from the triol glycerol
  (propan-1,2,3-triol)

and fatty acids.
178

• Fats and oils are esters.
• They are made from the triol glycerol
  (propan-1,2,3-triol)

and fatty acids.
179
Three fatty acids form esters with the three
OH groups of glycerol.
180
Three fatty acids form esters with the three
OH groups of glycerol.
181

• The hydrolysis of fats and oils produces fatty
  acids and glycerol in the ratio of three moles of
  fatty acid to one mole of glycerol.

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Fats and oils

• Fats and oils consist largely of mixtures of
  triglycerides.
• The three fatty acid molecules combined with each
  molecule of glycerol need not be the same.
• Soaps are produced by the hydrolysis of fats and
  oils.

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Proteins

• Nitrogen is needed to make protein in plants and
  animals.
• Proteins are condensation polymers made up of
  many amino acid molecules linked together.
• The structure of the protein is based on the
  constituent amino acids.

184
Amino acids

• These are compounds which contain an amine group
  and an acid group.

185

• There are about 25 essential amino acids.
• They are different because they have different
  side groups shown by R.
• Condensation of amino acids produces the peptide
  (amide) link.

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The peptide link

• The peptide link is formed when an acid and amine
  join together. (We have previously called this
  the amide link.)

187
The peptide link

• The peptide link is formed when an acid and amine
  join together. (We have previously called this
  the amide link.)

188
Amino acids polymerising
189
Amino acids polymerising
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Amino acids polymerising
191
Amino acids polymerising
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Building proteins

• Proteins specific to the bodys needs are built
  up within the body.
• The body cannot make all the amino acids required
  for body.
• We need protein in our diet to supply certain
  amino acids known as essential amino acids.

193
Digestion

• During digestion enzymes hydrolyse the proteins
  in our diet to produce amino acids.
• The body then builds up the amino acids it needs
  from those amino acids.

194
H2O
195
H2O
196
H2O
197
HO
198
Hydrolysis

• The structural formulae of amino acids obtained
  from the hydrolysis of proteins can be identified
  from the structure of a section of the protein as
  shown in the last few slides.

199
Types of proteins

• Proteins can be classified as fibrous or
  globular.
• Fibrous proteins are long and thin and are the
  major structural materials of animal tissue
  muscles, tissues etc.

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• Globular proteins have the spiral chains folded
  into compact units.
• Globular proteins are involved in the maintenance
  and regulation of life processes and include
  enzymes and many hormones, eg insulin and
  haemoglobin.

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Enzymes

• Enzymes, such as amylase, are biological
  catalysts
• An enzyme will work most efficiently within very
  specific conditions of temperature and pH.
• The further conditions are removed from the ideal
  the less efficiently the enzyme will perform.

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• What an enzyme can do is related to its molecular
  shape.
• Denaturing of a protein involves physical
  alteration of the molecules as a result of
  temperature change or pH change.
• The ease with which a protein is denatured is
  related to the fact that enzymes are very
  sensitive to changes in temperature and pH.

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Natural Products

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The End
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