REACTIONS OF ALKENES
Objectives:
• Describe the addition reactions of alkenes
• Explain how to distinguish between alkanes and alkenes using bromine water
• Understand the polymerisation reactions of alkenes
• Describe the economic importance of reactions of alkenes
? Alkenes are more reactive than alkanes. WHY?
- double bond is weaker than single bond.
- double bond (four electrons) represents a region of high electron density, and therefore attracts
electrophiles (electron lovers)
? The reactions of alkenes usually involve the C=C bond breaking to form a C–C bond.
The second component (π bond) of the C=C bond is weaker than a normal C–C single bond and is,
therefore, more easily broken.
Addition Reactions to Alkenes
(Mechanism: Electrophilic addition reaction)
? What is an electrophile?
An electrophile is a species that accepts a pair of electrons to form a new covalent bond.
It is attracted to electron-rich regions in other molecules or ions. Because it is attracted to a
negative region, an electrophile must be something which carries either a full (+) charge, or has a
slight (+) charge on it somewhere.
H+, CH3+, AlCl3 are examples for electrophiles.
? What is an nucleophile?
A nucleophile is a reactant that provides a pair of electrons to form a new covalent bond.
Cl─, Br─, NH3, H2O are examples for nucleophiles.
? What is an addition reaction?
1
An addition reaction is a reaction in which two molecules join together to make a bigger one.
Nothing is lost in the process. All the atoms in the original molecules are found in the bigger one.
The molecule X–Y is added either side of the double bond, which breaks to a single bond.
R stands for an alkyl group or H in
① Addition of halogens to Alkenes
• Alkenes react with halogens (F2, Cl2, Br2, I2) at room temperature.
The reaction with I2 is very slow at room temperature.
Mechanism:
② Addition of hydrogen to Alkenes (Hydrogenation)
• Alkenes react with hydrogen when heated in the presence of a catalyst, such as finely divided
nickel, to form alkanes
2
• Margarine is made from vegetable oils (liquids) by partial hydrogenation.
Mechanism:
③ Addition of hydrogen halide to Alkenes (Halogenation)
• Alkenes can react with hydrogen halides such as HBr by bubbling the alkene through a
concentrated solution of the hydrogen halide at 100 °C.
The reaction with HI is also rapid, but that with HCl is very slow, and a catalyst (such as AlCl3) is often
used for that reaction.
Mechanism:
3
④ Alkenes and Water (hydration)
• This process is called catalytic hydration and is used industrially for the production of ethanol,
an important solvent.
• Industrially, the process is carried out by reacting ethene with steam at 300 °C and 60 atm
pressure with an H3PO4 catalyst.
Example-1: Draw out the structures of the products of the following reactions by showing their
mechanisms.
but-2-ene + HBr ⟶
4
Example-2: Draw out the structures of the products of the following reactions by showing their
mechanisms.
pent-2-ene + chlorine ⟶
Example-3: Draw out the structures of the products of the following reactions (which occur under the
appropriate conditions):
a) but-1-ene + hydrogen
b) hex-3-ene + hydrogen bromide
c) pent-2-ene + chlorine
d) but-2-ene + water
Example-4: Write an equation for the formation of the following compounds from an appropriate
alkene:
5
Distinguishing between alkanes and alkenes
method → shaking them with _______________________________________
The bromine water
• ________________________________
• __________________________ to __________________________ when shaken with an ________________________
• there is __________________________ in colour when it is shaken with an ________________________
Note: Use the term _________________________ do not use _____________________. (_____________________________)
Alkene: _________________________________________________________
Alkane: _________________________________________________________
The reaction that occurs with an alkene is:
Addition polymerisation
6
Alkenes
• addition polymerization
• a large number of monomers are joined together into a polymer chain
The general equation
• Only the C=C group that reacts when the polymerisation reaction occurs – all the other groups
attached to the C=C are unaffected.
• The repeat unit or repeating unit of a polymer is the basic unit from which the whole
polymer chain can be made up (shown in brackets)
Example-5: Poly(ethene)
Example-6: PVC [poly(vinylchloride)]
• also known as (poly(chloroethene)
• chloroethene monomers → poly(chloroethene)
Example-7: Poly(propene)
7
The repeat unit for a polymer may be obtained simply by taking any
two adjacent carbon atoms in the main polymer chain:
The monomer for a polymer can be derived by simply placing a double
bond between the carbons of the repeat unit:
Economic importance of polymers
8
• commonly known as plastics extensive uses in everyday life.
• poly(ethene) → plastic bags, washing-up bowls and bottles
• poly(chloroethene) → electrical insulation and window frame
• poly(propene) → car bumpers and carpet fibres
• produced in vast quantities by the petrochemical industry but
• present a huge environmental problem
- using crude oil (petroleum) → limited natural resource
- disposing of them after use → non-biodegradable.
Example-8: Draw two repeat units for the polymers formed from the following alkenes:
Example-9: Draw the monomers for the following polymers:
9
? Electrophilic addition reaction:
Electrophilic addition to alkenes takes the following general form:
nuc: = nucleophile
E+ = electrophile
Electrophilic addition to alkenes starts with the pi electrons attacking an electrophile, forming a
carbocation on the most stable carbon. A nucleophile then attacks the carbocation to form the
product. There are many different kinds of such addition, including:
10
