Alkenes

 Unsaturated hydrocarbons because can make more bonds with extra atoms in addition
reactions.
 cnH2n
 Contain at least 1 double C-C covalent bond meaning high electron density so they are very
reactive.

Addition Reactions
Electrophilic addition reactions

 Double bond opens up, atoms added to C atoms.

 Happens because double bond has plenty of e- and easily attacked by electrophiles.
 Electrophile – electron pair acceptors.

Mechanisms for electrophilic addition reactions

General equation for this reaction using ethane and electrophile X-Y.

CH2CH2 + X-Y  CH2XCH2Y

1) C=C double bond repels X-Y e- which polarises X-Y bond.

2) 2 e- from C=C attack slightly +ve X atom which creates bond between 1st C and X. X-Y bond
breaks, e- from bond taken by Y atom and –ve ion formed with lone pair e-. C 2 is left +ve so
now there’s a carbocation intermediate.
3) Y- ion acts as nucleophile, attacks +ve
carbocation and donates its e- pair, forms
new bond with 2nd C.
4) So X-Y molecule added to alkene across
double bond to form saturated compound.
Bromine Test for Unsaturates

Shake alkene with orange bromine

water solution quickly changes from
orange to colourless. Bromine added
across double bonds to form colourless
dibromoalkane (happens by
electrophilic addition)

Major and Minor products

Adding hydrogen halides to unsymmetrical

alkene gives us two possible products.

The amount of each one formed depends on how stable carbocation formed in middle of reaction.
Known as carbocation intermediate. 3 possible carbocations:
Carbocation’s with more alkyl groups are more stable because alkyl group feeds e- toward +ve
charge. Can show alkyl group is donating e- by drawing arrow on bond pointing to where e- donated.

More stable ones more likely

to form than less stable so more product formed via more stable carbocation than less stable.
Addition Polymers

 Formed from alkenes and substituted alkenes (where 1 H atom swapped for another atom
or group, e.g. swapping 1 H in ethane for Cl atom you get chloroethene when polymerised
you get poly(chloroethene)). Long chain formed by several monomers joined.
 Can be natural or synthetic.
 Double bonds in alkenes can open up and join together, make long chain called polymer.
This is called addition polymerisation.

Written like:

To find monomer used take repeating unit and remove unnecessary side bonds and add double
bonds:
IUPAC Nomenclature

Once found monomer used to form addition polymer you know they form poly(X) where X is the
name of the monomer.

Polymer Properties –

 Alkene monomers unsaturated, once polymers they are saturated.

 Main C chain of polyalkenes is usually non-polar which means polyalkenes are very
unreactive.
 The monomers in polymer chain have strong covalent bonds but weak intermolecular forces.
Long chains, fewer branches have strong intermolecular forces so the polymers are strong
and rigid.

Polyethene – no branches so packed close together, chains attracted by VDW so strong & rigid.

Polystyrene (poly(phenylethene)) – Benzene ring coming off main C chain is large branch so
difficult for chains to pack closely. So only form weak WDV. They are more flexible.

Polychlorethene (polyvinyl chloride/PVC) – Covalent bonds between Cl and C are polar, Cl more
electronegative. Slightly –ve charge on Cl and slightly + on C means permanent dipole – dipole
forces between polymer chains. So PVC is hard but brittle, used for drainpipes and window
frames.

Plasticisers – Can add these chemicals to polymers to modify properties. Makes polymers bendier.
Chemicals get between chains and push apart which reduces strength of intermolecular forces so
chains can slide and move more so more flexible.

Plasticised PVC used to make electrical cable insulation, floor tiling and clothing.