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Organic Chemistry

St Stithians College
Set by: Mr F Gray
2010-11-24
Organic molecules
Organic chemistry is defined as the chemistry of
compounds that consist primarily of carbon and
hydrogen.

Atoms of nitrogen, oxygen, halogens, sulphur and


phosphorus are also sometimes part of organic
molecules.

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St Stithians College
The chemistry of carbon
Carbon atoms have the ability to form strong
covalent bonds with other carbon atoms and also
with atoms of other non-metals.

Carbon atoms bond with other carbon atoms to


form chains or ring structures. These chains can
be thousands of atoms long.

Catenation – the ability of carbon atoms to bond


with themselves to form chain or ring structures.
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St Stithians College
Important features of carbon
Allotropes of carbon exist. Graphite and diamond are
two examples.
Diamond Graphite

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Carbon has a valency of 44. This means it can form 4
bonds and has 4 valence electrons (4 electrons in the
outermost energy level).

Carbon will form a maximum of FOUR bonds with


other elements.

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A carbon atom in the ground
state
2p

2s

1s

Electron configuration: 1s²² 2s


2s²²2p
2p²²

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A carbon atom in the “excited”
state
2p

2s
Couper
1s
C Structure

Electron configuration: 1s²² 2s


2s¹¹2p
2p³³

In the excited state, valence electrons are unpaired


i.e. the 2s electron moves to higher 2p orbital.
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The hydrocarbons
Hydrocarbons – organic molecules that are made up of
carbon and hydrogen atoms only.
H H H
Alkanes H C H H C C H
H H H

Saturated hydrocarbons – hydrocarbon which has all


four bonds to the carbon atoms in its structure
singularly occupied.
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The Hydrocarbons
Unsaturated hydrocarbons – organic molecules which
have multiple bonds (double or triple) to the carbon
atoms within its structure.
H H
Alkenes
H C C H

Alkynes H C C H

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Homologous series
Homologous series – a family of organic molecules
which are identified by the same functional group and
obey the same general formula.

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Functional group
Functional group – a bond, atom or group of atoms in
the organic molecule which identifies to which
homologous series that molecule belongs and is
responsible for the chemical properties of that molecule.

Functional group s of hydrocarbons:

Alkanes Alkenes Alkynes

C C C C C C
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Naming the hydrocarbons No of C Prefix
Number the longest continuous chain atoms
of carbon atoms from the end nearest
1 Meth
the functional group. This determines
the prefix of the name. 2 eth -
3 prop -
The functional group determines
4 but -
the suffix:
5 pent -
Alkanes (single bonds) end in -ane.
6 hex -
Alkenes (double bond) end in -ene.
yne
Alkynes (triple bond) end in –yne
yne. 7 hept -
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8 oct -
Types of formulae
Structural formula – the structure of an organic
molecule showing all the bonds to all the atoms in the
molecule.
H H H H H H H H
1 2 3 4 1 2 3 4
H C C C C H H C C C C H
H H H H H H

Butane But-2-ene

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Types of formulae
Semi (condensed) structural formula – the structure of
an organic molecule that only shows the most important
bonds in the molecule.

CH CH CH CH 3 CH CH CH CH
3 2 2 3 3
Butane But-2-ene

CH C C CH 3
3
But-2-yne
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Types of formulae
Molecular formula – only indicates the number and
types of atoms present in the organic compound.

C3H8 C5H10 C3H4


Draw the structural formulae for these molecules and name them.
General formula:
Alkanes Alkenes Alkynes

CnH2n+2 CnH2n CnH2n - 2


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Alkanes
Alkanes are non-polar molecules containing only carbon
and hydrogen atoms. They are hydrocarbons with single
bonds between the carbon atoms.
They are saturated
saturated. This makes the alkanes quite
unreactive
unreactive.

As the size of the molecule increases


increases, the strength
of the van der Waal
Waal’’s forces increases hence
boiling points increase
increase. Methane to butane are
gases followed by liquids. The larger molecules (more
than 12 carbon atoms) are solids at room temperature.
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Name these alkanes and write down the molecular formula
for each molecule.

methane ethane propane

CH4 C2H6 C3H8

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Alkenes
The alkenes contain at least one double bond
between two carbon atoms. This makes them
unsaturated hydrocarbons.

The simplest alkene is ethene (ethylene).

Ethene is an important commercial organic chemical


and is used to make the plastic polythene
(polyethylene).
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1 2 3 4

H2C = CH – CH2 – CH3

But - 1 - ene

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Alkynes
The alkynes contain at least one triple bond between
two carbon atoms.
This makes them unsaturated hydrocarbons.
The simplest alkyne is ethyne (acetylene).
The combustion of ethyne and oxygen releases a
massive amount of heat. (3 000 0 C). It is used in the
oxyacetylene torch to cut metals.

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1 2 3 4
HC � C – CH2 – CH3

But-1-yne

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Branched organic molecules
Alkyl substituent – a carbon based “side chain” which is
attached to the longest continuous carbon chain in an
organic molecule.

Alkyl group structure Alkyl name


CH3 - methyl
CH3-CH2- ethyl
CH3-CH2-CH2- propyl
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Rules for naming organic
compounds (IUPAC rules)
1.Identify the functional group of the molecule – this
determines the ending of the name.

Br Cl H CH
3
H C C C C CH
3
H H CH
2
CH
3

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ene
Alkene
2. Find the longest continuous carbon chain that
contains the functional group, and allocate its prefix
according to the number of carbon atoms in the
chain (see table for prefixes).

Br Cl H CH
3
H C C C C CH
3
H H CH
2
CH
3

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6 carbon atoms = hex
hexene.
Number the carbon atoms in the chain. Number
3.Number
them so that the functional group is on the carbon of
lowest possible number
number. Double and triple bonds
take preference over side chains.

Br Cl H CH
3
1 2 3 4
H C C C C CH
3
5
H H CH
2
6CH
3

2-ene.
hex -2
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4.Name the alkyl group according to the number of
carbon atoms it has and give it a number according to
the carbon atom it is attached to. Alkyl groups must be
named in alphabetical order
order.

Br Cl H CH
3
1 2 3 4
H C C C C CH
3
5
H H CH
2
6CH
3

4,4-di-methyl
4,4-di-methyl-hex-2-ene
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5.If a halogen atom is attached to the carbon chain, it is
treated as an alkyl group. The prefixes: fluoro
fluoro-, chloro
chloro-,
bromo -, and iodo – are used. They must be named in
alphabetical order
order.

Br Cl H CH
3
1 2 3 4
H C C C C CH
3
5
H H CH
2
6CH
3

1-bromo-2-chloro-4,4-di-methyl-hex-2-ene
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6.If there is more than one alkyl group of the same
kind
kind, use the Greek prefixes di
di, tri and tetra to
indicate this.

Br Cl H
1 2 3 4 5
Cl C C C C CH
3
Cl Br H

1,2-di--bromo-
1,2-di 1,1,2-tri
bromo-1,1,2-tri -chloro-pent-2-
1,1,2-tri-chloro-pent-2-
yne
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Branched organic molecules
1 2 3 4

CH3 – CH – CH2 – CH3


CH3

2–methyl-butane
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Branched organic molecules

1 2 3 4

CH3 – CH – CH – CH3
CH3 CH3

2,3
2,3––di-methyl-butane
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Branched organic molecules

CH3
1 2 3 4 5
CH3 CH2 C CH2 CH3
CH2
CH3

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3-ethyl-3-methyl-pentane
Branched organic molecules

1 2 3 4
H2C = CH – CH – CH3
CH3

3–methyl-but-1 -ene

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Branched organic molecules
CH3
1 2 3 4
H2C = CH – C – CH3
CH3

3,3––di-methyl-but-1-ene
3,3
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Branched organic molecules

1 2 3 4

HC � C – CH – CH3
CH3

3-methyl-but-1-yne
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Dienes
These alkene molecules contain two double bonds
situated throughout the longest continuous carbon
chain.

Examples
1 2 3 4 5

H2C = C – CH = CH – CH3
(a)
CH3
2–methyl–penta–1,3-diene
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1 2 3 4 5

(b) H2C = C – CH2 CH = CH


6
CH3 CH3

2–methyl–hexa–1,4-diene

1 2 3 4
(c) H2C = C = C – CH3
CH3

3–methyl–buta–1,2-diene

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Diynes
These alkyne molecules contain two triple bonds
situated throughout the longest continuous carbon
chain.

Example
1 2 3 4 5
HC C – CH – C CH
CH3
3–methyl–penta–1,4-diyne
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Isomerism
Examine the two structural formulae shown below. Both are
structural formulae with molecular formulae C6H14
CH
3
CH 3 C CH CH CH CH CH CH CH
3 2 2 3
2 3
CH CH
3 3
2,2-di-methyl-butane 2-methyl-pentane
These two molecules are said to be ISOMERS.

Isomer s– organic molecules which has the same molecular


formula but different structural formulae.
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Alkyl halides (Haloalkanes)
Functional group: C X

where X = F, Cl, Br, I

Draw the structural formula for:


(a) chloromethane
(b) 1,1,1-tri-chloro-ethane
(c) 2-bromo-2-chloro-1,1,1-trifluoro-ethane
(d) 3-bromo-2-chloro-2- methyl-butane

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Alcohols
Ethanol is used widely as a solvent in paints, glues,
perfumes, aftershaves and any other household
products.

The strong hydrogen bonds in alcohols result in alcohols


having higher melting and boiling points than
hydrocarbons of similar size.

Functional group: C OH Hydroxyl group

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Alcohols
Alcohol molecules have a non-polar hydrocarbon end
and a polar –OH section.
Polar end
Non -
polar
end

Alcohols are solvents for polar and non-polar solutes.

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Alcohols
Alcohols are named using the ending –ol. Number
the longest chain beginning at the end nearest the
hydroxyl group. (OH)

ethanol propan-1-ol 2-methyl-propan-1-ol

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Alcohols

Propan-2-ol Butan-2-ol Pentan-3-ol

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Alcohols

2-methyl-propan-2-ol 2-methyl-butan-2-ol

CH2 – CH – CH2 Propan – 1,2,3, - triol

OH OH OH Glycerine/Glycerol
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Alcohols
Alcohols are oxidized to carboxylic acids when treated
with strong oxidizing agents.

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Carboxylic acids
The first member of the acid series is methanoic acid
(CHOOH). This acid can be found in stinging nettles and
ants.
O

H C OH
O
Functional group: Carboxyl group C OH

The names end in –oic acid. They are relatively weak


acids.
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Carboxylic acids
Ethanoic acid is the sour component of vinegar.

CH3 C OH

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Carboxylic acids
Butanoic acid gives the unpleasant smell to rancid
butter.

O
CH3 CH2 CH2 C OH

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Carboxylic acids
Nomenclature
CH3 Number the longest
carbon chain beginning
4 3 2 1 at the carboxyl group.
CH3 – C – CH2 – C - OH (COOH)

CH3 O

3,3-di-methyl-butanoic acid

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Esters
Esters are the compounds which are largely responsible
for the flavours and scents of fruits and flowers. Esters
are used as food flavourings and in perfumes and used
as solvents and adhesives.
O
Functional group: C O C

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Esters
An ester is the product of an acid catalysed
condensation reaction between an alcohol and a
carboxylic acid.
Nomenclature
O The prefix in the name of
the ester is derived from
CH3 - C - O - CH3 the ALCOHOL and the
suffix from the name of the
Acid Alcohol ACID. The name ends in -
OATE
methyl ethanoate
Methanol Ethanoic acid
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Ester formation (esterification)
Acts as a catalyst and
dehydrating agent
O H2 SO4
(Concentrated)

CH3 – CH2 – CH2 – C - OH + H O CH2 CH2 CH3


butanoic acid propan-1-ol

Oxygen link
O (‘bridge’)

CH3 – CH2 – CH2 – C - O CH2 CH2 CH3 + H2O

H2SO4
(Concentrated)
butanoic acid + propan-1-ol propyl butanoate + water

carboxylic acid + alcohol ester + water


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ethanoic acid + ethanol ethyl ethanoate + water

NB. Use the oxygen atom as a divider when naming the


molecule.

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Name the following REACTANTS
O butan-1-ol
+
CH3 – CH2 – C - O CH2 CH2 CH3 CH3
propanoic acid

butyl propanoate
O
methanol
CH3 – O - C CH2 CH2 CH3 CH3
+
pentanoic acid

methyl pentanoate
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Draw the products
H H O

H C OH + H C C OH

H H
methanol ethanoic acid
H2 SO4 H
(Concentrated) O H
H C O C C H + H2O

H H
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Aldehydes
O
Functional group: C H carbonyl group

The simplest aldehyde is methanal (Formaldehyde). In aldehydes,


the C=O on an outer carbon is polar
polar.
O
H C H
Nomenclature
Aldehydes are named by attaching the suffix ‘-al
al
al’’.
The longest chain is numbered beginning at the end nearest to the carbonyl
group.
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Aldehydes
1. H
4. CH3
H- C = O
CH2 - CH - CH3
Methanal
H- C = O
2. CH3
3–methyl butanal
H-C=O
Ethanal 5. CH3

CH - CH2 - CH - CH2 - CH3


3. CH2 - CH3
H-C=O CH3
H-C=O
Propanal 2,4-di-methyl hexanal

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Ketones O
Functional group: C carbonyl group

In a ketone, the carbon atom in the carbonyl group is bonded to a


carbon on both sides. The simplest ketone is propanone (acetone).

O
CH3 C CH3

In ketones, the C=O (carbonyl group) on an inner carbon is polar


polar.

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Ketones

Nomenclature

Ketones ( R – CO – R� ) are named by attaching the suffix ‘ –


one’.

The longest chain is numbered beginning at the end nearest to the


carbonyl group. The C in the carbonyl group has the lowest
number.

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Ketones
1. 3. O
O
CH3 CH C - CH2 CH2 CH3
CH3 - C - CH3
CH3
propanone

2–methyl hexan-3-one

2. O 4. O CH3
CH3 CH2 - C - CH2 CH2 CH3 CH3 CH - C - CH2 CH CH3
CH3
hexan-3-one

2,5-di-methyl-hexan-3-one
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Intermolecular forces
Intermolecular forces exist between molecules in the solid,
liquid or gas phase.

The strength of these forces decreases from solids to


liquids to gases.

Higher melting and boiling points indicate stronger


intermolecular forces within the substance.

The strength of the intermolecular forces increases with


increasing size of the molecule.
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Van der Waals forces
These are weak forces between particles carrying small
positive and negative charges.

They are non-directional and act over distances which


are large in comparison to the size of the molecule.

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Van der Waals forces
1. Dipole-dipole:

Attraction between the end of one polar molecule


and the end of another.

Aldehydes and ketones form polar molecules


δ +
Van der Waals force

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Van der Waals force
2. Temporary dipoles:
Non-polar molecules can form induced (temporary) dipoles
when the nucleus of one molecule attracts the electron
cloud of another.

Hydrocarbons and some alkyl halides form non-polar


δ
molecules. Van der Waals force

These are very weak forces but they increase in strength as
the length of the chain increases because they act over a
larger surface area.
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Hydrogen bonds
These intermolecular forces occur between molecules that
contain hydrogen bonded to a small highly electronegative
atom such as N; O; or F.
Hydrogen bond force

δ +

The H end of one molecule attracts the end of


another molecule.
Hydrogen bonds are stronger than v.d. Waals forces
and act over shorter distances
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Hydrogen bonds
Alcohols and carboxylic acids can form hydrogen bonds
between the molecules.

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Physical properties
Molecules in solids and liquids are held together by
intermolecular forces.

To move the molecules apart requires energy; the stronger


the I.M. forces the greater the energy required.

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Trends in physical properties
Boiling and melting points increase as the strength of the I.M.
forces increase.

Molecules which form hydrogen bonds will have higher m.p


and b.p than those with v.d Waals forces.

Molecules with longer chains will have higher m.p and b.p
than those with shorter chains.

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Trends in physical properties
Vapour pressure is the pressure which the vapour
above a liquid exerts on the surface of the liquid.

Substances with weak I.M. forces will vapourize easily.

A high vapour pressure indicates weak I.M. forces.

Alkyl halides vapourize readily so they are used as


propellants in aerosol sprays.

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Trends in physical properties
Viscosity. This is an indication of how “runny” a liquid is.
A liquid with low viscosity flows easily.

As the length of the carbon chain increases, the I.M.


forces become stronger and liquids become more
viscous.

Liquids in which the molecules can form hydrogen bonds


will have a higher viscosity.

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Solvent properties
For the molecules of one substance to mix with
molecules of another, the I.M. forces between the
molecules must be of the same kind and strength.

We say a solid dissolves in a liquid or that two liquids


are miscible.

Alkyl halides form non-polar molecules and this makes


them important solvents for fats and oils which also
have non-polar molecules.
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Solvent properties
The hydrocarbons form non-polar molecules and
therefore they do not dissolve in water which is held
together by hydrogen bonds.

Simple alcohols mix readily with water because of their


ability to form hydrogen bonds.

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Combustion reactions
Alkanes
Alkanes, alkenes and alkynes burn in oxygen and form carbon
dioxide and water
water.

The reaction is exothermic and a great deal of energy is


released.

Alkanes
Propane is the gas used in bunsen burners in the laboratory.
Propane burns as follows:

C3H8 + 5O2 → 3CO2 + 4H2O + energy


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Combustion reactions
If propane burns in limited oxygen then carbon
(black) is produced:

C3H8 + 2O2 → 3C + 4H2O

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Combustion reactions
Alkenes
Ethene burns with a blue flame.

C2H4 + 3O2 → 2CO2 + 2H2O + energy

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Combustion reactions
Alkynes
Ethyne is used, along with oxygen, in an oxy-acetylene
torch, which is used to cut metals.

2C2H2 + 5O2 → 4CO2 + 2H2O + energy

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Combustion reactions
Alcohols burn in oxygen to form carbon dioxide and
water.
Ethanol

C2H5 OH + 3O2 → 2CO2 + 3H2O + energy

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Addition reactions
Addition reactions take place when a double or triple
bond is broken and new molecular fragments are added
to both ends of the bond with nothing being taken away.

If we break the double bond in ethene, each carbon will


have one electron to bond to a new atom.

H H H H
H C C H H C C H
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Addition reactions
H H

H C C H

We can then add the following:


Hydrogen H2 A halogen Cl2
H H H H
H C C H H C C H
H H Cl Cl
ethane
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Addition reactions
H H

H C C H

We can then add the following:


A hydrogen halide HCl Water H2O
H H H H
H C C H H C C H
H Cl H OH
1-chloro-ethane
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ethanol
Addition reactions
Hydrogenation
CH2 = CH2 + H2 → CH3 – CH3
ethene ethane

Halogenation (chlorination)
CH2 = CH2 + Cl2 → CH2Cl
CH2Cl–– CH2Cl
alkene alkyl halide

Hydrohalogenation
CH2 = CH2 + HCl → CH3
CH3–– CH2Cl
alkene
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alkyl halide
Addition reaction
Hydration (addition of water)
CH2 = CH2 + H2O → CH3 – CH2- OH
alkene alcohol

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Test for a double bond
To test for a double bond, react the compound with
bromine.

The red-brown colour of the bromine rapidly disappears


if a double bond is present, due to the addition reaction
that takes place.

CH2 = CH2 + Br2 → CH2Br


CH2Br–– CH2Br
red-brown colourless

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Elimination reactions
Elimination reactions take place when atoms or
molecular fragments are removed from adjacent atoms
in a molecule leaving a double bond with nothing being
added. This is the exact opposite of addition.

Eliminating hydrogen
CH3 - CH3 → CH2 = CH2 + H2

Eliminating a halogen
CH3Cl - CH3Cl → CH2 = CH2 + Cl2
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Elimination reactions
Eliminating hydrogen halide
CH3 - CH3Cl → CH2 = CH2 + HCl

Eliminating water
CH3Cl – CH2OH → CH2 = CH2 + H2O

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Substitution reactions
Substitution reactions take place when one atom is replaced
by another.
Example 1: (Alkane becomes alkyl halide)
Halogens such as chlorine will substitute into an alkane
molecule in the presence of sunlight. The chlorine uses the
sunlight to separate into chlorine atoms.
H H
Cl – Cl + energy → 2Cl + H C H H–Cl + Cl C H
H H

One chlorine atom bonds with a hydrogen atom and the


other chlorine atom takes its place.
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Substitution reactions
Example 2: (Alcohol becomes alkyl halide)
Cl replaces OH in a molecule of ethanol.

H H H H
H – Cl + H C C OH H C C Cl + H2O
H H H H

HCl + C2H5OH → C2H5Cl + H2O


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Substitution reactions
Example 3: (Hydrolysis)
Bases (or water) with haloalkanes produce alcohols.

H H H H
KOH + H C C Br H C C OH + KBr
H H H H

KOH + C2H5Br → C2H5OH + KBr


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Plastics and Polymers
Plastics are made by joining small molecules which have
C = C bonds into very long chains which have C–C
bonds.

The small molecules are known as monomers.

The long chains are called polymers.

The process is known as addition polymerisation.


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Definitions
Macromolecules – very large molecules having
molecular weights that may be several millions of atomic
mass units.

Monomers – small similar molecules which can join to


make a chain.

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Polymers – long chains of
monomers which are
covalently bonded
together.

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Polymerization – the process by which monomers join
to make a chain.

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1. Addition polymerization
There are three steps in the production of the chain:
1. Initiation: The reaction is initiated by a free radical,
which is a molecular fragment with an unpaired electron.
R
The free radical adds to the double bond of the
monomer and creates another free radical
radical.

H H H H
R + C C R C C
H H H H
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The pi bond of the carbon – carbon double bond is broken.
2. Propagation: The new free radical adds to the double
bond of another monomer molecule and creates another
free radical with a longer chain.

H H H H H H H H
R C C + C C R C C C C
H H H H H H H H

Successive additions of this kind happen very fast and a


chain may grow to 1000 units or more within a second.

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3. Termination: This is the step which terminates the
chain.
The formation of the chain will end if:
(a) two radicals join together

H H H H H H H H
R C C C C + C C C C R
H H H H H H H H

H H H H H H H H
R C C C C C C C C R
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H H H H H H H H
The formation of the chain will end if:
(b) one radical removes a hydrogen atom from another
radical forming an alkane and an alkene.

H H H H H H H H
R C C C C + C C C C R
H H H H H H H H

H H H H H H H
R C C C C H + C C C C R
H H H H H H H H
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2. Condensation
polymerization
These polymers are made from two different monomers
which have reactive groups at both ends of their
molecules.
Long chain of
HO CH2 CH2 OH carbon atoms.

a dialcohol A molecule with two OH groups.

O O
HO C C OH

a dicarboxylic acid A molecule with two COOH groups.


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The monomers join to each other in an alternating
structure and eliminate a small molecule, such as H2O.

O O

HO OH + HO C C OH

O O
HO O C C OH + H2O

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ester
O O

O O C C

a polyester

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Making a polyester
Example:
O O

HO CH2 CH2 OH + HO C CH2 C OH


ethan-1,2-diol propan-1,3-dicarboxylic acid

O O O O

- O - CH2 - CH2 - O - - C - CH2 - C - - O - CH2 - CH2 - O - - C - CH2 - C -

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a polyester
Draw two repeating units of the polyester when the
following monomers are used:
O O
HO - CH2 - OH + HO - C - (CH2)2 - C - OH

=
O O O O
- O - CH2 – O - C - (CH2)2 - C - O - CH2 – O - C - (CH2)2 - C -
=

=
H2O molecules are eliminated
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Plastics
Plastics are man made macromolecules.

Properties of plastics

They are polymers of carbon.


They are light because the atoms from which they are
made are small.
They are strong because the molecules are long. The
longer the molecules the stronger the intermolecular
forces.
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They are unreactive, this means that they are difficult
to dispose of because they will not rot away – they are
not biodegradeable.

They are electrical and thermal insulators.

Some plastics catch fire easily and they may give out
poisonous gases.

They are divided into two groups called thermoplastics


and thermosets.
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Thermoplastics
These plastics contain long thin molecules with tangled
chains. The forces between the chains are weak Van
der Waals forces.

This means that the chains can move easily over each
other on heating, flexing and stretching.

Thermoplastics melt on heating and when cool they set


into a new shape.

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Thermosets
They contain a network of large molecules with strong
cross-links which form when the plastic is made.

This means that on stretching the molecules cannot


slide over each other.

They will char or break down at high temperatures,


rather than melt.

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They are rigid and will break rather than bend.

They are moulded into shape when they are being made,
because the shape cannot be changed later.

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