Organic Chemistry Chapter 14

Hydrocarbons

14.2 – ALKENES (Part 2)

 Oxidation Reaction of Alkenes
Cold, dilute acidified manganate(VII) ions
• Potassium manganate(VII) is a strong oxidising agent.

• Manganate(VII) ions can oxidise alkenes to form diols (alkane with two alcohol groups).

• For this reaction to take place, the manganate ions must be cold, dilute and acidified.

• The colour change depends on whether the potassium manganate(VII) is used under
acidic or alkaline conditions.

• If the potassium manganate(VII) solution is acidified with dilute sulphuric acid, the purple
solution becomes colourless.
 Oxidation Reaction of Alkenes
• If the potassium manganate(VII) solution is made slightly alkaline (often by adding sodium
carbonate solution), the purple solution first becomes dark green and then produces a
dark brown precipitate.

• In the reaction below, [O] denotes the oxidising agent:

• Manganate(VII) ions are a strong oxidising agent, and in the first instance oxidise ethene
to ethane-1,2-diol
 Oxidation Reaction of Alkenes
Hot, concentrated acidified manganate(VII) ions
• When an alkene reacts with hot, concentrated, acidified manganate(VII) ions the C=C
double bond, ruptures.

• Further reactions then take place, depending on the groups attached to the carbons

• The manganate(VII) ions oxidise the alkene by breaking the C=C bond and replacing
it with a C=O double bond on each new molecule.
 Oxidation Reaction of Alkenes
Oxidation of alkene might produce carbonyl compounds such as aldehyde and ketones
What is aldehyde and ketone?
Structure carbonyl groups consists of
a carbon-oxygen double bond

the bond is polar due to the

difference in electronegativity

Difference
ALDEHYDES KETONES
- at least one H attached to the carbonyl group - two carbons attached to the carbonyl group
 Oxidation Reaction of Alkenes

o If both the R groups in the

product are alkyl groups
then a ketone will form.
Ketones are not easily
oxidised so no further
oxidation takes place.
 Oxidation
OxidationReaction
ReactionofofAlkenes
Alkenes

o If a product has one alkyl group

and one hydrogen then an
aldehyde will be produced.
Aldehydes are easily oxidised to
carboxylic acids as the final
product.
 Oxidation
OxidationReaction
ReactionofofAlkenes
Alkenes

o If both R groups in the product

are hydrogen atoms, methanal
will be formed. This is oxidised
to methanoic acid which is then
oxidised to form water and
carbon dioxide.
 Addition Polymerisation
• Alkenes can undergo addition polymerisation. In this reaction, many alkene
monomers join together to form a polymer.
• Polymer: a long chain molecule made up of many repeating unit derived from
monomers.

• Monomers: small molecule that react together to make polymers

• Alkenes are able to react and form polymers because their C=C double
bonds can open up, allowing the carbons to join together.

• The polymers produced are saturated because they do not contain any
carbon-carbon double bonds.
 Addition Polymerisation
Repeating units
• Repeat units are the section of polymer which repeats throughout the whole
chain.
• They can be easily drawn as they look the same except that the double carbon-
carbon bond is drawn as a single bond and single bonds are drawn coming out
the sides of each carbon atom:
 Addition Polymerisation
Identifying repeating unit and monomer

• First, split the polymer chain into its

repeat units.
n
• With an addition polymer, then put the
C═C double bond back into the
monomer:
 Addition Polymerisation
Characteristics of addition polymerisation
• Addition polymers are very unreactive.

• This is because the polyalkene chains are saturated and the main carbon
chain is non-polar.

• The chains are held together by i.d-i.d forces since there is generally no
polarity in the main carbon chain.

• Polymers made up of straight chains are strong and rigid because the chains
are able to lie closer together and so there are more points of contact and
stronger i.d-i.d forces.

• Polymers made up of branched chains are usually weaker by comparison

 Polymerisation
Poly(ethene)
• Poly(ethene) is produced from the addition polymerisation of ethene. During
this reaction, lots of ethene monomers join together to produce one long chain
polymer product.

• For the equation above, the ‘n’ denotes a large number of units reacting
together to form a chain with this unit length.
 Addition Polymerisation
Poly(chloroethane) @ Polyvinyl chloride (PVC)
 Addition Polymerisation
Poly(chloroethene) @ Polyvinyl chloride (PVC)

Repeating unit

n
 Addition Polymerisation
Poly(propene) (PP)
nC3H6  [C3H6]n
EXERCISE 1 & 2
EXERCISE 3 & 4
EXERCISE 5 & 6
EXERCISE 7 & 8
EXERCISE 9
THE
END