Reactions of Alkenes

Unit 2_Module 1: The Chemistry of Carbon Compounds Functional Group Analysis
Reactions of Alkenes
Alkenes are a family of hydrocarbons (compounds containing carbon and hydrogen only)
containing ONE carbon-carbon double bond. They contain a multiple bond and thus are called
UNSATURATED molecules.
Alkenes have an electron rich center i.e. partially negative region, the double bond or Π bond.
Alkanes do not have either a partially positive or negative region. Therefore alkenes are
susceptible to electrophilic attack but alkanes are NOT susceptible to either electrophile or
nucleophile attack. Hence alkenes are more reactive than alkanes.
Since alkenes are reactive compounds, they are NOT used as fuels like alkanes but as building
blocks in the petro-chemical industry.
1. Halogenation
Ethene and chlorine / bromine
In each case you get an addition reaction. For example, bromine adds to give 1, 2-
dibromoethane.
The reaction with bromine happens at room temperature. If you have a gaseous alkene like
ethene, you can bubble it through either pure liquid bromine or a solution of bromine in an
organic solvent like tetrachloromethane. The reddish-brown bromine is decolourised as it
reacts with the alkene.
2. Reaction with hydrogen halides
Addition to symmetrical alkenes
All alkenes undergo addition reactions with the hydrogen halides. A hydrogen atom joins to
one of the carbon atoms originally in the double bond, and a halogen atom to the other. For
example, with ethene and hydrogen chloride, you get chloromethane:
Conditions
The alkenes react with gaseous hydrogen halides at room temperature. If the alkene is also a
gas, you can simply mix the gases. If the alkene is a liquid, you can bubble the hydrogen
halide through the liquid.
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Addition to unsymmetrical alkenes

Orientation of addition
If HCl adds to an unsymmetrical alkene like propene, there are two possible ways it could
add. However, in practice, there is only one major product.
This is in line with Markovnikov's Rule which says:
When a compound HX is added to an unsymmetrical alkene, the hydrogen becomes attached

to the carbon with the greater number of hydrogen atoms attached to it already.
In this case, the hydrogen becomes attached to the CH2 group, because the CH2 group has 2
hydrogen atoms and the CH group only has one hydrogen atom attached.
3. Oxidation of Alkanes
With cold KMnO4/H+
Alkenes react with potassium manganate (VII) solution in the cold. Manganate (VII) ions are
a strong oxidising agent, and in the first instance oxidize ethene to ethane-1, 2-diol.
With hot KMnO4/H+
The hot conc. potassium manganate (VII) solution oxidizes the alkene by breaking the
carbon-carbon double bond and replacing it with two carbon-oxygen double bonds. Two
fragments are produced.
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Carbonyl compounds can also react with potassium manganate (VII), but how they react
depends on what is attached to the carbon-oxygen double bond. So we need to work through
all the possible combinations.
Carbonyl compounds which have two hydrocarbon groups attached to the carbonyl group are
called ketones. Ketones aren't that easy to oxidize, and so there is no further action. If the
groups attached either side of the original carbon-carbon double bond were the same, then
you would end up with a single ketone. If they were different, then you would end up with a
mixture of two.
If one of the R groups attached to the carbon atom is a hydrogen atom, then it would form the
corresponding carboxylic acid.
If both R groups are hydrogen atoms then it is further oxidized to carbon dioxide and water.
4. Hydration
Reaction with conc. Sulphuric acid at 1700C
In the lab, ethanol is produced by reacting ethene with concentrated sulphuric acid with
concentrated sulphuric acid at 170 °C.
In industry, ethanol is manufactured by reacting ethene with steam. The reaction is

reversible.
Only 5% of the ethene is converted into ethanol at each pass through the reactor. By
removing the ethanol from the equilibrium mixture and recycling the ethene, it is possible to
achieve an overall 95% conversion.
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A flow scheme for the industrial preparation looks like this:
5. Hydrogenation
Ethene reacts with hydrogen in the presence of a finely divided nickel catalyst at a
temperature of about 150°C. Ethane is produced.
Some margarine is made by hydrogenating carbon-carbon double bonds in animal or

vegetable fats and oils. You can recognize the presence of this in foods because the
ingredients list will include words showing that it contains "hydrogenated vegetable oils" or
"hydrogenated fats". If there are two or more carbon-carbon double bonds in each chain, then
it is said to be polyunsaturated. However, there are possible health benefits in eating mono-
unsaturated or polyunsaturated fats or oils rather than saturated ones - so you wouldn't want
to remove all the carbon-carbon double bonds.
One problem arises from the hydrogenation process. The double bonds in unsaturated fats
and oils tend to have the groups around them arranged in the "cis" form.
The relatively high temperatures used in the hydrogenation process tend to flip some of the
carbon-carbon double bonds into the "trans" form. If these particular bonds aren't
hydrogenated during the process, they will still be present in the final margarine in molecules
of trans fats.
The consumption of trans fats has been shown to increase cholesterol levels (particularly of
the more harmful LDL form) - leading to an increased risk of heart disease.
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Alkenes react via the electrophilic addition mechanism

Using ethene and bromine as an example:-
Note: The arrows show the movement of the electrons towards a positively charged region.
In the first stage of the reaction, one of the bromine atoms becomes attached to both carbon
atoms, with the positive charge being found on the bromine atom. A bromonium ion is
formed.
The bromonium ion is then attacked from the back by a bromide ion formed in a nearby
reaction.
Reactions of Alcohols
Alcohols can be classified as primary (1°), secondary (2°) and tertiary (3°) alcohols.
 Tertiary alcohol = all 3 R groups are alkyl groups e.g. 2-methylpropan-2-ol
 Secondary alcohol = 2 of the 3 R groups are alkyl groups e.g. propan-2-ol
 Primary alcohol = zero or one of the R groups is an alkyl group e.g. ethanol
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Unit 2_Module 1: The Chemistry of Carbon Compounds Functional Group Analysis

Addition to unsymmetrical alkenes

This is in line with Markovnikov's Rule which says:

When a compound HX is added to an unsymmetrical alkene, the hydrogen becomes attached

With hot KMnO4/H+

In industry, ethanol is manufactured by reacting ethene with steam. The reaction is

A flow scheme for the industrial preparation looks like this:

Some margarine is made by hydrogenating carbon-carbon double bonds in animal or

Alkenes react via the electrophilic addition mechanism

 Tertiary alcohol = all 3 R groups are alkyl groups e.g. 2-methylpropan-2-ol

 Secondary alcohol = 2 of the 3 R groups are alkyl groups e.g. propan-2-ol

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