14 Alkenes

●● TEST YOURSELF ON PRIOR KNOWLEDGE 1

1 a) H H H H

H C C C C Br

H H H H
b) The source of the hydroxide ions is potassium hydroxide as it is
more soluble in ethanol than sodium hydroxide. The reagent and the
halogenoalkane are dissolved in ethanol.
c)
H H H H H H H
_
δ_
H C C C C δ+
Br H C C C C +H2O+ Br
H
H H H H H H H
–
OH
d) Butan-1-ol may be produced as elimination and nucleophilic
substitution reactions can occur but the elimination will be more
probable in ethanolic conditions.

●● TEST YOURSELF 2
1 a) H H
H C
C C H
H H
b) H H H
1
H C C C C
H H Cl H
 c) H H H H
H C C C C C C H
H H H H
H C H
H C H
H
H
d)

2 a)
Structural isomers
H H H H H
C C C C H H C C C C H
H H H H H H H H
but-1-ene positional isomers but-2-ene

H
H C H
H H
C C C H
H H
2-methylprop-1-ene-a chain isomer

Steroisomers
H H H H
14 ALKENES

C H H C C H
H C C H C C
H C H H H H
H H
E-but-2-ene Z-but-2-ene

b) E-Z isomerism is a feature of the alkenes as they contain a

2 double bond and rotation is restricted about a double bond.
Halogenoalkanes do not contain a double so rotation is not
restricted.
3 a) The higher priority groups in this molecule are on the same side of
the plane of the double bond. Each carbon atom in the double bond
is considered separately.
On the left hand side the carbon is bonded directly to a carbon atom
above and below. These carbon atoms are each bonded directly to
a further carbon atom. At the top this carbon atom is bonded to a
 carbon and two hydrogens while at the bottom the carbon is bonded
to three hydrogen atoms. The top group is the higher priority group.

TEST YOURSELF 4
Using the same reasoning the top group on the right-hand side is the
higher priority group. As the higher priority groups are on the same
side of the plane of the C=C the molecule is classified as a Z isomer.
b) Z-4-ethyl-3-methylhept-3-ene

●● TEST YOURSELF 3
1 a) poly(chloroethene)
b) poly(tetrafluroroethene)
2 drainpipes/window or door frames/clothing/electrical insulation for wiring
3 a) H H
C C
H H
b) CH3H
C C
H H (CH3 in any position)

c) Cl H
C C
Cl H (Cl on same C atom)

●● TEST YOURSELF 4
1 a) i) An electrophile is an electron pair acceptor.
ii) A nucleophile is an electron pair donor.
iii) Heterolytic fission is the breaking of a bond into two differently
charged fragments.
iv) Homolytic fission is the breaking of a bond into two free radicals.
b) i) Br2 → Br− + Br+
ii) Br2 → ●Br + ●Br
3
 2 a) H H
H H
_
C C H C C H + Br
+
H H H
δ+ δ_
H Br

H H
H C C H
H Br
b) CH2CH2 + HBr → CH3CH2Br
c) bromoethane
d) electrophilic addition
e) carbocation
3 a) Bromine will react with ethene in the dark at room temperature in an
electrophilic addition reaction to produce 1,2-dibromoethane and no
other product. The bromine molecule is polarised when it is in the
proximity of the C=C of the alkene and undergoes heterolytic fission
to produce a bromide ion which adds to a reactive carbocation
intermediate.
Bromine will react with ethane in the presence of ultraviolet light
to form a mixture of brominated alkanes which may have one or
more bromine atoms, up to a maximum of six. Butane is also found
in the product mixture. Hydrogen bromide gas is also produced.
The reaction is a free radical substitution reaction. It is a chain
reaction which happens in three steps: initiation, propagation and
termination. In the initiation step UV light supplies the activation
energy to break the Br–Br bond homolytically to form two bromine
radicals, each with an unpaired electron.
14 ALKENES

b) i) Br2 + CH4 → HBr + CH3Br

There are various other equations which you can write
depending on the product as a mixture of brominated alkanes
are formed.
2Br2 + CH4 → 2HBr + CH2Br2
3Br2 + CH4 → 3HBr + CHBr3
4
4Br2 + CH4 → 4HBr + CBr4
ii) Br2 + CH3CHCHCH2CH3 → CH3CHBrCHBrCH2CH3
c) Add the organic compound to bromine water. The yellow-orange
bromine water will become colourless if the organic compound
contains a double bond.
●● TEST YOURSELF 5

TEST YOURSELF 5
1 a) i) A carbocation is a positive ion where the positive charge centres
on a carbon atom in the molecule.
ii) Carbocations can be classified according to the position of
the positively charged carbon in the molecule. A secondary
carbocation is one where the positively charged carbon atom is
along the carbon chain or is attached to two R groups.
b) Tertiary carbocations are more stable than secondary carbocations
which are more stable than primary carbocations due to the positive
inductive effect of the alkyl groups attached to the positively
charged carbon. Alkyl groups donate electron density towards the
C+ reducing the value of the positive charge and stabilising the
carbocation. Tertiary carbocations have three alkyl groups attached
while secondary carbocations have two and primary carbocations
have one or no alkyl group attached.
2 a) i) H H H H
H C C C C C C H
H H H H H H
ii)
H H H H H H
H C C H H C C C C H
H H C C H H H H H H
C C
H C C H
H H H H
E-hex-3-ene but-2-ene

b) Hex-2-ene is an asymmetrical alkene; E and Z hex-3-ene are

symmetrical alkenes.

5
 c)
H3CH2C CH2CH3
C C
H H
+ _
Hδ Brδ

H3CCH2 CH2CH3 H3CCH2 CH2CH3

H C C H H C C H
+ +
H H
_ _
Br Br
CH3CH2CH2CHBrCH2CH3 CH3CH2CHδCH2CH2CH3
3-bromohexane 3-bromohexane

d) H H H H
H C C C C C C H
H H H H H H
δ+ _
H Brδ

H H H H H H H H H H H H
H C C C C C C H H C C C C C C H
+ +
H H H H H H H H H H
_ _
Br Br
14 ALKENES

CH3CH2CHBrCH2CH2CH3 CH3CHBrCH2CH2CH2CH3
3-bromohexane 2-bromohexane

●● ACTIVITY
6
Making ethene
1 fractional distillation
2 The breaking up of large molecules into smaller ones using heat.
3 C10 H20 → C2H4 + C8H16
4 CH3–CH2–OH conc H2SO4 CH2=CH2 + H2O
5 The first portion of the gas evolved is displaced air from the apparatus.
6 As the gas cools it contracts and this would cause the solution in the
wash bottle to suck back. Sodium hydroxide and concentrated sulfuric
acid would be a dangerous violent reaction.