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Unit 2 Mod 1 Alkenes
Unit 2 Mod 1 Alkenes
Alkenes page1 of 8
Alkenes (Module 1)
a) state the general formula of alkenes
b) know and identify the functional group in alkenes
c) understand that alkenes are much more reactive than alkanes and explain why
this is so
d) appreciate that alkenes are not used as fuels but as building blocks to produce
other chemicals
e) describe the chemical reactions of alkenes (with conditions)
i) combustion (include colour of flame) ii) halogenation
iii) oxidation (hot and cold) iv) hydration v) hydrohalogenation
vi) hydrogenation (include production of trans-fat which are harmful)
and give equations for each chemical reaction
f) state the name of the mechanism by which alkenes use and describe the
mechanism using ethene and bromine as an example
g) define Markovnikov’s Rule and apply it to the prediction of products for the
reaction of hydrogen halides and UNsymmetrical alkenes
propene C3H6
You can work out the formula of any of them using the general formula: CnH2n
The functional group is the double bond C=C
Since alkenes are reactive compounds, they are NOT used as fuels like alkanes
but as building blocks in the petro-chemical industry.
1. Combustion
With oxygen or air to carbon dioxide and water (in excess oxygen) if oxygen is
limited, carbon monoxide and water are the products
e.g. C2H4 + 3O2 2CO2 + 2H2O alkenes burn with a smoky yellow flame
Unit 2 mod 1 chem. Alkenes page2 of 8
2. Addition (all unsaturated compounds undergo addition reactions)
a) Hydrogenation
Ethene reacts with hydrogen in the presence of a finely divided nickel catalyst at
a temperature of about 150°C. Ethane is produced.
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.
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.
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.
Unit 2 mod 1 chem. Alkenes page3 of 8
Using bromine water as a test for the presence of a multiple bond
If you shake an alkene with bromine water or bromine liquid (or bubble a
gaseous alkene through bromine water), the solution becomes colourless.
Unsaturated compounds decolourise bromine water.
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.
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.
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.
Unit 2 mod 1 chem. Alkenes page4 of 8
d) Oxidation of alkenes
Alkenes react with potassium manganate(VII) solution in the cold.
Manganate(VII) ions are a strong oxidising agent, and in the first instance
oxidise ethene to ethane-1,2-diol (old name: ethylene glycol).
:
The formula below the general form of all alkenes. The R groups represent alkyl
groups.
The products are known as carbonyl compounds because they contain the
carbonyl group, C=O. 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 oxidise, 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.
For example:
Unit 2 mod 1 chem. Alkenes page5 of 8
Please note that 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 oxidised to carbon
dioxide and water.
e) Hydration
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.
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.
Unit 2 mod 1 chem. Alkenes page7 of 8
Worksheet
1 a)
b) Draw the structural formula when retinol reacts with excess bromine in
tetrachloromethane
ii) Show the structural formula of the product when retinol is reacted with
hydrogen gas
iii) Show the structural formula of the product when retinol is reacted with
steam