Organic Chemistry 2013

ORGANIC CHEMISTRY
UNIT 10
UNIT 20 HL
UNIT 20 HL ONLY
A series of compounds that have the same functional group (and hence similar
chemical properties) is said to form an homologous series.
In these homologous series:

10.1.2 Predict and explain the trends in boiling points of members of a homologous series.
BOILING AND MELTING POINTS DEPEND MAINLY ON

THE INTERMOLECULAR FORCES PRESENT
10.1.3 Distinguish between empirical, molecular and structural formulas.
10.1.4 Describe structural isomers as compounds with the same molecular formula
but with different arrangement of atoms
 Isomers are different compounds with the same molecular formula
 Isomers are going to have different physical compounds (melting and boiling points)
and also different chemical properties depending on the type of isomerism
Hydrocarbons Chain Isomers
Isomers of Butane
Isomers of Pentane
Positional isomers
Functional Group
Isomers
NAMING HYDROCARBONS
ONLY HL
NAMING HYDROCARBONS
Use these rules to model and draw the five structural isomers of hexane
Name the following compounds
VOLATILITY
10-2 ALKANES
General formula for the homologous series of alkanes

CnH2n + 2
10.2.1
Explain the low reactivity of alkanes in terms of bond enthalpies and bond polarity.
 Due to their strong intermolecular forces between their C and H elements which need
a strong source of energy to react alkanes are stable molecules under most of the
circumstances.
 Alkanes are non polar hydrocarbons so they are not soluble in polar compounds like
water
 These two properties influenced the low reactivity of alkanes
10.2.2
Describe, using equations, the complete and incomplete combustion of alkanes.
Complete combustion of octane (C8H18), a major component of gasoline:

Incomplete combustion
Substitution reactions of alkanes
 A substitution reaction involves the replacement of one atom with another atom.
 The alkanes can undergo substitution reactions, primarily reactions in which halogen
atoms replace hydrogen atoms.
 In order for this to occur, the covalent bond between the carbon atom and the
hydrogen atom that is going to be replaced must be broken, and the bond between
the reacting atoms (in this case halogen atoms) must also be broken.
Methane can react with bromine in a series of substitution reactions that occur
very rapidly by a free-radical mechanism.
The Br–Br bond is weaker than the C–H bond and will be easier to split:
Br2 → Br· + Br· ΔH = +193 kJ mol −1
CH4 → CH3· + H· ΔH = + 435 kJ mol− 1

Alkenes
Alkene series has the general formula CnH2n
 Alkenes are an example of an unsaturated hydrocarbon.
 Unsaturated hydrocarbons contain at least one carbon–carbon double bond, and so

contain less than the maximum number of hydrogen atoms.
 Alkenes exhibit the same trends in properties as the alkanes: as the molecular
length increases, the boiling point and melting point increase, because the strength
of the van der Waals’ forces increases.
Alkenes can also exhibit structural isomerism. The double bond may occur in
different places along the chain, or branching may occur.
Exercise
 Deduce , draw and name the structural formulas for the different isomers of the straight chains
alkenes up to C6
10.3.1
Describe, using equations, the reactions of alkenes with hydrogen and halogens.
 Alkanes undergo substitution reactions, but alkenes undergo addition reactions.

 In an addition reaction, two substances react together to form a single product.
For example, ethene reacts readily with chlorine to produce 1,2-dichloroethane.

 Alkenes also undergo an addition reaction with hydrogen. This reaction, sometimes
called hydrogenation, results in the formation of a saturated hydrocarbon, an alkane.
The reaction of ethene with hydrogen using a catalyst is shown below:
Nickel is the used catalyst in this reaction but platinum or palladium can be also
used as catalyst in hydrogenation reaction.
This reaction is widely used in the food industry like in margarine production
10.3.2
Describe, using equations, the reactions of symmetrical alkenes with hydrogen halides
and water.
 Alkenes can also react with hydrogen halides and with water.
 An important industrial addition reaction is the reaction between ethene and water.
This process, called hydration, is very important in the manufacture of ethanol.
 Ethene and steam are passed over a catalyst (phosphoric acid on silica) at 300°C and 70
atm pressure. The purpose of the phosphoric acid is to provide a lower activation energy
pathway for the reaction. Hydrogen ions, H+, are supplied by the phosphoric acid. These
ions take part in the reaction but are regenerated at the end.
The reaction to make ethanol is an exothermic reaction and would be favoured by low
temperatures, at which the rate of reaction would be unacceptably low, so a catalyst is used
in conjunction with moderately high temperatures and moderately high pressures
10.3.3
Distinguish between alkanes and alkenes using bromine water
 The reaction between alkenes and bromine is used to distinguish between an alkene
and an alkane.
 Both hydrocarbons are colourless and so cannot be distinguished by sight. Pure
bromine is a red liquid that becomes yellow/orange in solution.
 When bromine water is added to an alkene, the colour of the bromine disappears
immediately (that is, decolourization occurs) as the addition reaction occurs.
 The reaction between an alkane and bromine will not proceed unless a strong source of
UV light is available.
10.3.4
Outline the polymerization of alkenes.
 A polymer (poly means ‘many’) is made up of very large chain-like molecules. These
have been generated by the reaction of thousands of monomers (mono means ‘one’)
that have joined together as repeating units in the chain.
 The production of poly(ethene) is an example of an addition polymerization reaction.
This refers to reactions in which the monomer contains a double bond. When the
monomers join to each other, the double bond converts to a single bond and the
second pair of electrons previously in the double bonds are used to form covalent
bonds between the monomers.
Ethene is a hydrocarbon, and so is non-polar.
This leads to weak intermolecular forces between the poly(ethene) chains
 Two other common addition polymers are poly(chloroethene), better known as PVC
(short for its old name of PolyVinyl Chloride), formed by the polymerisation of
chloroethene and polypropene, formed by the polymerisation of propene
The effect of the chlorine in the poly chloroethene is to introduce a significant
dipole into the molecule, increasing the attraction forces and as a result
increasing the melting point and lowering the flammability of the polymer
when it is compared with a polyethene .
The propene monomer has one double bond and can be regarded as an ethene
molecule in which a hydrogen atom has been replaced by a methyl group.
10.3.5
Outline the economic importance of the reactions of alkenes.
 Alkenes are of great economic importance to society. Although alkenes occur

naturally in only small quantities, when crude oil is put through the process of
cracking, large amounts of alkenes can be obtained. In cracking (thermal cracking
or catalytic cracking) alkanes with large molecular masses are broken into small
alkenes and relatively small alkanes. This provides a source of alkenes, which have
a wide variety of uses, and, at the same time, uses up the large, less useful
alkanes.
 Alkenes provide the starting materials for a wide range of synthetic polymers
(plastics) that we depend on for so many uses. One of the most widely used
alkenes is ethene. It can be changed into ethanol by the process of hydration, and
it forms the basis of many polymerization reactions in which plastics are formed.
 All of these polymers are produced in very high tonnages for the manufacture of a
wide variety of products, hence these polymerisation reactions are economically
very important.
 The reason is that the changes to the monomer often lead to a unique or
enhanced property. For example, the use of CH3 in polypropene leads to a melting
point that is about 60°C higher than that of polyethene. This allows polypropene
to be used in microwave ovens and dishwashers.
 Teflon (poly (tetrafluorothene)) is a polymer that combines a non stick surface
with an extremely high melting point. Its formula is (C2F4)n.
 The great length and molecular mass of the polymer chains means that polymers
have much higher melting points than their small molecular mass monomers
 In the manufacture of margarine, polyunsaturated vegetable oils (which have
many carbon–carbon double bonds) are converted into a soft, low melting point
solid by the addition of extra hydrogen. This creates a spread that closely
resembles butter.

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ORGANIC CHEMISTRY

In these homologous series:

BOILING AND MELTING POINTS DEPEND MAINLY ON

 Isomers are different compounds with the same molecular formula

General formula for the homologous series of alkanes

Complete combustion of octane (C8H18), a major component of gasoline:

Br2 → Br· + Br· ΔH = +193 kJ mol −1

CH4 → CH3· + H· ΔH = + 435 kJ mol− 1

Alkene series has the general formula CnH2n

 Alkenes are an example of an unsaturated hydrocarbon.

 Unsaturated hydrocarbons contain at least one carbon–carbon double bond, and so

 Alkanes undergo substitution reactions, but alkenes undergo addition reactions.

For example, ethene reacts readily with chlorine to produce 1,2-dichloroethane.

The reaction of ethene with hydrogen using a catalyst is shown below:

 Alkenes are of great economic importance to society. Although alkenes occur

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