Organic Chemistry
Organic Chemistry
Organic Chemistry
Displayed Formulae
Organic Chemistry is the scientific study of the structure, properties, and reactions of
organic compounds.
Organic compounds are those which contain carbon
For conventional reasons metal carbonates, carbon dioxide and carbon monoxide
are not included in organic compounds
Many of the structures you will be drawing are hydrocarbons
A hydrocarbon is a compound that contains only hydrogen and carbon atoms
Organic compounds can be represented in a number of ways:
o Displayed Formulae
o General Formulae
o Structural Formulae
The displayed formula shows the spatial arrangement of all the atoms and bonds in a
molecule
For example:
Structural Formulae
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In structural formulae, enough information is shown to make the structure clear, but
most of the actual covalent bonds are omitted
Only important bonds are always shown, such as double and triple bonds
Identical groups can be bracketed together
Side groups are also shown using brackets
Straight chain alkanes are shown as follows:
Structural Isomers
Structural isomers are compounds that have the same molecular formula but different
structural formulae
The molecular formula is the actual number of atoms of each element in a compound
Compounds with the same molecular formula can have different structural formulae due
to the different arrangement of their atoms in space
Two examples of structural isomers are shown below
Exam Tip
Remember: Only double and triple bonds are shown in structural formulae.
Homologous Series
This is a series or family of organic compounds that have similar features and chemical
properties due to them having the same functional group
The functional group is a group of atoms which are bonded in a specific arrangement
that is responsible for the characteristic reactions of each member of a homologous
series
Exam Tip
Make sure you can identify the functional group for each homologous series.
General Formulae
General Formulae
This type of formula tells you the composition of any member of a whole homologous
series of organic compound
For example, all of the alkanes have the general formula C nH2n+2, where n represents the
number of carbon atoms
This tells you that however many carbon atoms there are in the alkane, doubling this
number and adding two will give you the number of hydrogen atoms present in the
alkane
General formulae can be used to work out the formula of a compound from different
homologous series if the number of carbon atoms present is known
Alkanes CnH2n+2
Alkenes CnH2n
Alcohols CnH2n+1OH
Worked Example
What is the formula of an alcohol that contains 5 carbon atoms?
Answer
Number of carbons = 5
Formula = C5H11OH
Worked Example
A compound has the formula C12H24. To which homologous series does this compound
belong to?
Answer
There are 12 carbon atoms, so n = 12
There are twice the number of hydrogen atoms than carbon atoms = 2n
Therefore the general formula of the compound is C nH2n which means this compound is
an alkene
Exam Tip
Make sure you learn the general formula for each homologous series.
Saturated & Unsaturated Compounds
Saturated compounds have molecules in which all carbon-carbon bonds are single
bonds
Examples of compounds that are saturated are alkanes
Alkanes are saturated hydrocarbons with the general formula CnH2n+2
The names of organic compounds have two parts: the prefix (or stem) and the end part
(or suffix)
The prefix tells you how many carbon atoms are present in the longest continuous chain
in the compound
The suffix tells you what functional group is on the compound
Structures of organic compounds
Exam Tip
Make sure you can draw and name the structures given above.
When there is more than one carbon atom where a functional group can be located it is
important to distinguish exactly which carbon the functional group is on
Each carbon is numbered and these numbers are used to describe where the functional
group is
For example:
o Propan-1-ol is alcohol with an -OH functional group
o The 2 in the name indicates that the -OH group is located on the second carbon
atom
In propan-1-ol the -OH group is located on the first carbon atom
Alkanes
Alkenes
Alcohols
Carboxylic acids
Esters
1 Fossil Fuels
Common Fossil Fuels
Petroleum is also called crude oil and is a complex mixture of hydrocarbons which also
contains natural gas
It is a thick, sticky, black liquid that is found under porous rock (under the ground and
under the sea)
Diagram showing crude oil under the sea
Petroleum itself as a mixture isn't very useful but each component part of the mixture,
called a fraction, is useful and each fraction has different applications
The fractions in petroleum are separated from each other in a process
called fractional distillation
The molecules in each fraction have similar properties and boiling points, which
depend on the number of carbon atoms in the chain
The boiling point and viscosity of each fraction increase as the carbon chain gets
longer
Fractional Distillation
Viscosity
o This refers to the ease of flow of a liquid.
o High viscosity liquids are thick and flow less easily.
o If the number of carbon atoms increases, the attraction between the hydrocarbon
molecules also increases which results in the liquid becoming more viscous with
the increasing length of the hydrocarbon chain.
o The liquid flows less easily with increasing molecular mass
Colour
o As carbon chain length increases the colour of the liquid gets darker as it gets
thicker and more viscous
Melting point/boiling point
o As the molecules get larger, the intermolecular attraction becomes greater.
o More heat is needed to separate the molecules.
o With increasing molecular size there is an increase in boiling point
Volatility
o Volatility refers to the tendency of a substance to vaporise.
o With increasing molecular size hydrocarbon liquids become less volatile.
o This is because the attraction between the molecules increases with increasing
molecular size
Uses of Fractions
Exam Tip
When defining a hydrocarbon, ensure you say that it has hydrogen and carbon
atoms only.
Alkanes: Properties & Bonding
This Table shows the Displayed Formula of the First Four Members of the Alkane
Homologous Series
Substitution Reaction of Alkanes with Halogens
Extended
In a substitution reaction, one atom (or group of atoms) is swapped with another atom
(or group of atoms)
Alkanes undergo a substitution reaction with halogens in the presence of ultraviolet
radiation (sunlight is a source of UV radiation)
This is called a photochemical reaction
The UV light provides the activation energy, Ea, for the reaction
A hydrogen atom is replaced with the halogen atom
More than one hydrogen atom can be substituted depending on the amount of
ultraviolet radiation there is
In the presence of ultraviolet (UV) radiation, methane reacts with chlorine to form
chloromethane and hydrogen chloride
Exam Tip
You need to be able to draw the displayed and structural formulae of the products
formed when one halogen atom replaces a hydrogen (also known as monosubstitution)
Catalytic Cracking
Although there is use for each fraction obtained from the fractional distillation of crude
oil, the amount of longer chain hydrocarbons produced is far greater than needed
These long chain hydrocarbon molecules are further processed to produce other
products
A process called catalytic cracking is used to convert longer-chain molecules
into short-chain and more useful hydrocarbons
Shorter chain alkanes, alkenes and hydrogen are produced from the cracking of longer
chain alkanes
Alkenes can be used to make polymers and the hydrogen used to make ammonia
Kerosene and diesel oil are often cracked to produce petrol, other alkenes and hydrogen
Cracking involves heating the hydrocarbon molecules to around 600 – 700°C
to vaporise them
The vapours then pass over a hot powdered catalyst of alumina or silica
This process breaks covalent bonds in the molecules as they come into contact with the
surface of the catalyst, causing thermal decomposition reactions
The molecules are broken up in a random way which produces a mixture of smaller
alkanes and alkenes
Hydrogen and a higher proportion of alkenes are formed at higher temperatures and
higher pressure
The 10 carbon molecule decane is catalytically cracked to produce octane for
petrol and ethene for ethanol
Exam Tip
When describing what happens to bromine water in an alkene ensure you say
colourless, and not clear.
Distinguishing from Alkanes
Distinguishing Between Alkanes & Alkenes
Exam Tip
When describing what happens to bromine water in an alkene ensure you say
colourless, and not clear.
Addition Reactions
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Alkenes undergo addition reactions in which atoms of a simple molecule add across the
C=C double bond
The reaction between bromine and ethene is an example of an addition reaction
Bromine atoms add across the C=C in the addition reaction of ethene and bromine
Alkenes also undergo addition reactions with hydrogen in which an alkane is formed
These are hydrogenation reactions and occur at 150ºC using a nickel catalyst
Hydrogenation reactions are used to manufacture margarine from vegetable oils
o Vegetable oils are polyunsaturated molecules which are partially hydrogenated to
increase the Mr and turn the oils into solid fats
Hydrogen atoms add across the C=C in the hydrogenation of ethene to produce an
alkane
Alkenes also undergo addition reactions with steam in which an alcohol is formed.
Since water is being added to the molecule it is also called a hydration reaction
The reaction is very important industrially for the production of alcohols and it occurs
using the following conditions:
o Temperature of around 300ºC
o Pressure of 60 - 70 atm
o Concentrated phosphoric acid catalyst
A water molecule adds across the C=C in the hydration of ethene to produce
ethanol
Exam Tip
You need to be able to draw the displayed formulae of the products of alkenes with
water, hydrogen and bromine.
Alcohols
All alcohols contain the hydroxyl (-OH) functional group which is the part of alcohol
molecules that is responsible for their characteristic reactions
Alcohols are a homologous series of compounds that have the general
formula CnH2n+1OH
They differ by one -CH2 in the molecular formulae from one member to the next
Diagram showing the first three alcohols
Hydration of ethene
o A mixture of ethene and steam is passed over a hot catalyst of phosphoric
acid at a temperature of approximately 300 °C
o The pressure used is 60 atmospheres (6000kPa)
o The gaseous ethanol is then condensed into a liquid for use
A water molecule adds across the C=C in the hydration of ethene to produce
ethanol
Fermentation of glucose
o Sugar or starch is dissolved in water and yeast is added
o The mixture is then fermented between 25 and 35 °C with the absence of oxygen
for a few days
o Yeast contains enzymes that catalyse the break down of starch or sugar to
glucose
o If the temperature is too low the reaction rate will be too slow and if it is
too high the enzymes will become denatured
o The yeast respire anaerobically using the glucose to form ethanol and carbon
dioxide:
The yeast are 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
Exam Tip
Make sure you learn the conditions for both hydration and fermentation.
Comparing Methods of Ethanol Production
Extended
Carboxylic Acids
2CH3COOH + Mg → (CH3COO)2Mg + H2
In the reaction with hydroxides, salt and water are formed in a neutralisation reaction
For example, the reaction between potassium hydroxide and propanoic acid forms the
salt potassium propanoate and water:
In the reaction with carbonates a metal salt, water and carbon dioxide gas are produced
For example, in the reaction between potassium carbonate and butanoic acid, the salt
potassium butanoate is formed with water and carbon dioxide
Exam Tip
You need to be able to name and give the formulae of the salts produced in these
reactions.
Formation of Ethanoic Acid
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Making Carboxylic Acids
The acidic, vinegary taste of wine which has been left open for several days is due to the
presence of ethanoic acid
Alternatively, oxidising agent potassium manganate(VII) can be used
This involves heating ethanol with acidified potassium manganate(VII) in the presence
of an acid
The heating is performed under reflux which involves heating the reaction mixture in a
vessel with a condenser attached to the top
The condenser prevents the volatile alcohol from escaping the reaction vessel as alcohols
have low boiling points
The equation for the reaction is:
Naming Esters
Diagram showing the origin of each carbon chain in ester; this ester is ethyl
butanoate
Polymers are large molecules built by linking 50 or more smaller molecules called
monomers
Each repeat unit is connected to the adjacent units via covalent bonds
Some polymers contain just one type of unit
o Examples include poly(ethene) and poly(chloroethene), commonly known as PVC
Others contain two or more different types of monomer units and which are
called copolymers
o Examples include nylon and biological proteins
Different linkages also exist, depending on the monomers and the type of
polymerisation
o Examples of linkages are covalent bonds, amide links and ester links
Diagram showing how lots of monomers bond together to form a polymer
Addition Polymers
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Addition polymers are formed by the joining up of many monomers and only occur in
monomers that contain C=C bonds
One of the bonds in each C=C bond breaks and forms a bond with the adjacent
monomer with the polymer being formed containing single bonds only
Many polymers can be made by the addition of alkene monomers
Others are made from alkene monomers with different atoms attached to the monomer
such as chlorine or a hydroxyl group
The name of the polymer is deduced by putting the name of the monomer in brackets
and adding poly- as the prefix
For example if propene is the alkene monomer used, then the name is poly(propene)
Poly(ethene) is formed by the addition polymerisation of ethene monomers
o Polymer molecules are very large compared with most other molecule
o Repeat units are used when displaying the formula
o To draw a repeat unit, change the double bond in the monomer to a single
bond in the repeat unit
o Add a bond to each end of the repeat unit
o The bonds on either side of the polymer must extend outside the brackets (these
are called extension or continuation bonds)
o A small subscript n is written on the bottom right hand side to indicate a large
number of repeat units
o Add on the rest of the groups in the same order that they surrounded the
double bond in the monomer
Exam Tip
You should be able to draw the box diagrams representing polymers where each box
represents a part of the repeating hydrocarbon chain. The functional groups on the
monomers and the link formed in the polymers are the important parts and must be
clearly drawn.
Condensation Polymers
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Condensation polymers are formed when two different monomers are linked together
with the removal of a small molecule, usually water
This is a key difference between condensation polymers and addition polymers:
o Addition polymerisation forms the polymer molecule only
o Condensation polymerisation forms the polymer molecule and
one water molecule per linkage
The monomers have two functional groups present, one on each end
The functional groups at the ends of one monomer react with the functional group on
the end of the other monomer, in so doing creating long chains of alternating
monomers, forming the polymer
Hydrolysing (adding water) to the compound in acidic conditions usually reverses the
reaction and produces the monomers by rupturing the peptide link
Forming Nylon
The structure of nylon can be represented by drawing out the polymer using boxes to
represent the carbon chains
Diagram showing a section of nylon
Forming Polyesters
The structure of PET can be represented by drawing out the polymer using boxes to
represent the carbon chains
This can be done for all polyesters
Diagram showing a section of PET
Exam Tip
You don't need to know the detailed chemical structure of PET, just the symbolic
drawing showing the alternating blocks and the linking ester group. Be careful not to
exactly repeat the linking group in nylon or PET; the link alternates by reversing the
order of the atoms, rather like a mirror image.
Synthetic polymers are ones made in a factory, for example nylon, terylene and lycra
Nylon is a polyamide used to produce clothing, fabrics, nets and ropes
PET, also known as Terylene, is a polyester made from monomers which are joined
together by ester links
PET is used extensively in the textile industry and is often mixed with cotton to
produce clothing
These are plastics which do not degrade over time or take a very long time to degrade,
and cause significant pollution problems
In particular plastic waste has been spilling over into the seas and oceans and is causing
huge disruptions to marine life
In landfills waste polymers take up valuable space as they are non-biodegradable so
microorganisms cannot break them down. This causes the landfill sites to quickly fill up
Polymers release a lot of heat energy when incinerated and
produce carbon dioxide which is a greenhouse gas that contributes to climate change
If incinerated by incomplete combustion, carbon monoxide will be produced which is a
toxic gas that reduces the capacity of the blood to carry oxygen
Polymers can be recycled but different polymers must be separated from each other
which is a difficult and expensive process
PET Re-polymerisation
PET stands for polyethylene terephthalate, a common polymer used to make things like
plastic bottles
It is a condensation polymer consisting of repeating ester units, so it is type of polyester,
like terylene
One of the problems with recycling polymers is that the condition needed to break them
down, which are usually high temperatures and pressures, can degrade the monomers
making them unusable for re-polymerisation
PET is relatively easy to convert back into the monomers
It can be depolymerised either using enzymes or by chemical methods
Enzymes present in microbes breakdown the PET into the original monomers
The same can be achieved using solvents a catalyst and mild heating
The breakdown of PET into its two monomers takes place using enzymes or
chemical catalysts and mild conditions
Proteins are condensation polymers which are formed from amino acid monomers
joined together by amide links (in proteins also known as a peptide link) similar to the
structure in nylon
The units in proteins are different however, consisting of amino acids
Amino acids are small molecules containing NH2 and COOH functional groups
There are twenty common amino acids, each differing by their side chain, represented
by R
Proteins can contain between 60 and 600 of these amino acids in different orders
These are the monomers which polymerise to form the protein
Diagram showing condensation polymerisation to produce a protein
The structure of proteins can be represented using the following diagram whereby the
boxes represent the carbon chains