Summary of Chemistry Textbook: Section 11.

4 Reactions of Alkenes
Addition reactions of alkenes
- Alkanes substitution reactions
- Alkenes addition reaction
- In an addition reaction, two substances react together to form a single product (the
reactants add together)
- A double carbon bond has a bond enthalpy of 612 kJ mol
-1
and the single carbon bond has a
bond enthalpy of 348 kJ mol
-1

- Therefore less energy required to break one half of a double bond than is needed to break a
single bond in an alkane, making alkenes much more reactive than alkanes
- The double bond can be converted to a single bond, allowing extra atoms or groups of atoms
to be added to the molecule
o E.g. ethene reacts readily with chlorine to produce 1,2-dichloroethane
o H
2
C=CH
2(g)
+ Cl
2
CH
2
ClCH
2
Cl
(l)

- Although ethane reacts with chlorine only in sunlight or at high temperatures, the high
reactivity of ethenes double bond means that chlorine readily reacts with ethene at room
temperature
- The addition of chlorine occurs across the double bond so that one chlorine atom attaches
to each carbon atom.
- Alkenes also undergo an addition reaction with hydrogen hydrogenation = formation of a
saturated hydrocarbon an alkane
- Nickel, platinum and palladium all used as catalysts in hydrogenation
- Hydrogenation reaction is particularly useful in the food industry
- Margarine is a butter substitute that is made from vegetable oils
- Vegetable oils = mixture of polyunsaturated fats which are recognised as a healthy
substitute for butter
- Hydrogen is added across some of the double bonds in the polyunsaturated fats and the oils
are converted to a soft, low melting point solid that is more like butter
- Alkenes can also react with hydrogen halides and with water
- Both these reactions are addition reactions
- Reaction between an alkene and a hydrogen halide provides a more controlled way to
produce a particular halogenoalkane than the substitution reaction between an alkane and a
halogen
- Double bond controls the position of the halogen atom in that it will be on one of the two
carbon atoms that were involved in the double bond
- An important industrial addition reaction is the reaction between ethene and water
- This process is called hydration and it is very important in the manufacture of ethanol
- Ethene and steam are passed over a catalyst (phosphoric acid on silica) at 300
o
C and 70 atm
pressure
- Purpose of 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 generated at the end
- Example of an industrial process in which a compromise must be reached between rate of
reaction and yield
- 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
- 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 disappears immediately (decolourisation occurs) as the addition reaction
occurs
- Reaction between an alkane and bromine will not proceed unless a strong source of UV light
is available
- Similarly, purple acidified potassium permanganate, KMnO
4
, is decolourised by reaction with
alkenes
Addition polymerisation
- 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
- Production of poly(ethene) is an example of an addition polymerisation 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
- There are no by-products in this process only one product forms
- As the product is directly related to just one reactant, the name of the product is always the
same as that of the reactant with poly added as a prefix
- Ethene polymerizes to make poly(ethene), propene polymerizes to make poly(propene)
- The equation can be written as follows, where n is a large number and represents the
number of repeating units in the polymer chain
o nCH
2
CH
2
(CH
2
CH
2
)
n

o ethene poly(ethene)