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ORGANIC

CHEMISTRY

Organic chemistry is the chemistry of carbon


compounds

Carbon is in the group 4 or 14 of the periodic table.

Carbon always forms covalent bonds.

As carbon has 4 electrons in its valence level (2,4)


it forms 4 covalent bonds.

When all of them are single bonds they have a


tetrahedral arrangement.

In organic molecules:

Carbon always forms 4 bonds.

Oxygen forms 2 bonds

Halogen and Hydrogen form 1 bond

Functional group

A homologous series is a series of compounds with the same


functional group, in which each member differs from the next by -CH2- .

Features of homologous series:!

Successive compounds differ from each other by a -CH2- group(methylene


group)

The compounds can all be represented by a general formula. eg. Alkanes =

CnH2n+2

The compounds have similar chemical properties.

Successive compounds have physical properties that vary in a regular manner as the
number of carbon atoms present increases.

Cambridge Chemistry 422

As the number of carbon atoms in a molecule in a particular homologous series


increases the boiling point increases. !

The boiling point of straight chain alkanes increases when a metalyne group is
added.

Reason:

As the relative molecular mass of the alkane increases the strength of the Van der
Waals forces between molecule increases.

The boiling point of the alcohols(-OH) tend to be higher due to the presence of
hydrogen bonding.

Other functional groups such as carboxylic acid (-COOH), amine(-NH2) and amide(CONH2) also gives rise to hydrogen bonding.

Therefore, they have higher melting and boiling point than non-polar or polar organic
compounds of similar molar masses.

The physical properties, especially the melting


and boiling point, depend on intermolecular
forces.

Some function groups such as Aldehyde and


Ketones give rise to polarity within molecules and
this results in Dipole-Dipole force hence slightly
higher melting and boiling point.

Hydrocarbons: Compound containing only C-H


bonds.

Empirical formula: The simplest whole number


ratio of the elements present in a compound.

Molecular formula: The total number of atoms of


each element present in the molecule of the
compound.

The full structural formula shows all the atoms


and bonds. eg. Butanoic acid.

A structural formula indicates in a fixed manner


how the atoms are arranged in the molecule.

An alkyl group CnH2n+1 because of the removal of 1


electron.

Alcohols can be expressed by the addition of the hydroxyl


group -OH.

Benzene ring:

Phenol-Benzene ring with -OH attached.

pg. 425 Cambridge

pg. 426 Cambridge

Isomers are different compounds which have the


same molecular formula.

Different isomers have different chemical and


physical properties

Structural isomers: Two or more compounds in


which the atoms are joint in a different order so that
they have the same molecular formula but
different structural formula.

pg. 426 Cambridge

Position isomers: Have the same hydrocarbon


skeleton and the same functional group:

The functional group is joined to a different part of


the skeleton.

eg. Propan-1-ol and propan-2-ol

Hydrocarbon chain isomers: Have different


hydrocarbon skeletons that the functional group
is attached to.

Example: Butane and methylpropane

Functional group isomers: Some functional


groups will usually have isomers containing
another functional group.

Example: Alcohols usually have an alcoxyalkane


that is isomeric to them hence ethanol has an
isomer methoxymethane.

Stereoisomers: The order that the atoms are


joined together is the same, but the molecules a
different arrangement of atoms in space and hence
3-d shapes.

In general, branched chain isomers have lower


boiling point then straight chain isomers. !

Reason: Branches prevent the main chains from


getting as close together and so Van der Waals
forces are weaker between the molecules.

Rules for IUPAC:

Find the longest continuous carbon chain.!

Use the prefix from the table to the number of carbon atoms in the longest
continuous carbon chain.

Look for the substituent groups(alkyle groups)!

Number the position of these substituent groups using the combination that
includes the lowest individual numbers.

Use the prefix to indicate the number of each substituent group!

Arrange the number of substituent groups in alphabetical order. eg. di, tri, tetra

Saturated-Carbon has a single bond can be eight


In an open or closed system

Unsaturated: Carbon has a double bond/triple


bond. In an open or closed system.

Benzene with ring = aromatic

Benzine without ring=aliphatic.

The alkanes are non-polar molecules with only


Van der Waals forces between molecules.

This means that they are volatile(evaporate easily)


with these first four members being gases at
room temperature.

Due to their non-polar nature, they are insoluble


in water.!

The most familiar reaction of alkanes is


combustion!

Complete combustion of hydrocarbons:


Requires the presence of excess oxygen and
produces carbon dioxide and water.

Complete combustion of ethane:!

pg. 432

INCOMPLETE
COMBUSTION

When there is a limited supply of oxygen,


incomplete combustion occurs, which produces
carbon monoxide, soot ( C ) and Water.

Example:

Alkanes react with chlorine or bromine in a


substitution reaction, to give an initial product in
which 1 hydrogen atom is replaced by the halogen.

Usually, these reactions take place by exposure to


UV light or sunlight, though they will also occur
without light at very high temperature.

eg.
Ethane

Chloroethane

The reaction of an alkane (methane), with a


halogen is a free radical chain reaction.!

The process can be split into 3 distinct changes:!

Initiation: Produces the radicals (reactive species


with unpaired electrons.

Propagation which forms most of the product in


which the radicals are reformed (that is one radical
is used up but another formed).

Termination: Which consumes radicals.

As a result, the initiation stage occurring once can


cause the propagation steps to occur many
times before the radicals are consumed in a
termination step.

The alkanes are said to be saturated


hydrocarbons because they contain only single
C-C bonds.

The compounds with multiple bonds are called


unsaturated hydrocarbons.!

The simplest unsaturated hydrocarbons are


alkenes, which contain a carbon-carbon double
bond.

The general formula for alkene homologous series


is CnH2n

Though double bond are stronger than single bond, they are not
twice as strong:
!
!

This means that it is energetically favorable for a double bond to


be converted into two single bonds.

The activation energy for these reactions is also relatively low,


owing to the high electron density in the double bond.

This means that alkenes are considerably more reactive than


alkanes.

Alkenes and hydrogen!

Alkenes react with hydrogen when heated in the


presence of a catalyst such as finely divided
nickel to form alkanes.

This reaction is called hydrogenation.

Reaction of alkenes and halogen!

Alkenes react with halogen at room temperature.

The reaction with iodine is very slow at room


temperature.

Alkenes and hydrogen halides!

Alkenes react with hydrogen halides (HBr) by


bubbling the alkene through a concentrated
solution of hydrogen halide at 100 degrees celcius.

The reaction with HI is rapid but that with HCl is


very slow.

So a catalyst such as AlCl-3 is used.

Alkenes and water!

Alkenes react with water to form alcohol.

Alkenes may be distinguished from alkanes by


shaking them with bromine water.

The bromine water, which is orange, is decolorized to


colorless when shaken with alkene.

There is no change in color when shaken with alkane.

Alkene: bromine water ->orange to colorless

Alkane: bromine water >no color change

Polymers are long chain molecules that are formed by


the joining together of a large number of repeating units,
called monomers by a process of polymerization.

Alkenes undergo addition polymerization in which a


large number of monomers are joined together into a
polymer chain.

It is important to realize that it is only the C C group


that reacts when the polymerization reaction occurs-all
the other groups attached to the C C are unaffected

Reaction page 443 Addition polymerization.


Cambridge

Poly(ethene)

In the production of low density poly(ethene) the


reaction takes place under high temperature and high
pressure in the presence of small amount of oxygen
or an organic peroxide.

In the production of high density poly(ethene) the


reaction takes place under much lower temperature
and lower pressure in the presence of a catalyst.

POLY(VINYL) CHLORIDE
(PVC)

It is made by polymerization of chloroethane


monomers at moderate temperature in the
presence of an organic peroxide.

POLY(PROPENE)

Poly(propene) is formed by the polymerization of


propene.

The polymers more commonly known as plastics are


extensively used in every day life.

Among other things polyethene is used for plastic bags


washing up bowls and bottles.

Polychloroethane is used for electrical insulation and


window frames.

Polypropene is used for car bumpers and carpet fibers.

ALCOHOLS

The functional group of alcohol is -OH.

The general molecular formula is CnH2n+1OH.

Alcohols have a much higher boiling point than


alkanes as a result of hydrogen bonding.

The lower members are soluble in water because


of hydrogen bonding.

Alcohols burn readily in air to form carbon dioxide


and water, hence they are used for fuels in the
presence of excess oxygen.

Primary alcohols !

Primary alcohols are oxidized first of all to an


aldehyde (partial oxidation)

Then the aldehyde is oxidized further to a


carboxylic acid (complete oxidation)