Ch7SumMARY Alkene

Download as doc, pdf, or txt
Download as doc, pdf, or txt
You are on page 1of 2

Alkenes

General Features
1.
2.
3.
4.

Unsaturated
The pair of electrons in thebond are more diffuse
Cannot rotate about the double bond
If double bond and single bond occurs alternately, resonance will
occur.( e.g. CH2=CH-CH=CH2), stability increases.

Important Points (Exam.)


Geometrical isomers
Rotation of the C-C double bond will destroy thebond. The restriction
to rotation of C-C double bond give rise to geometrical isomers.
Markownikoffs Rule
When a non-symmetrical electrophile is added onto the double bond of a
non-symmetrical alkene, the problem of orientation of addition arises.
Markovnikovs Rule : addition will take place so as to give the most
stable intermediate carbocation.
Addition will take place so as to give the most stable intermediate
carbocation.

CH2=CHCH3 + HBr

CCl4

CH3CHBrCH3

Mechanism
CH2=CHCH3 + H-Br

CH 3CHCH3 + Br
CH3CHBrCH3

Decolourization of permanganate solution


- cold
CH2=CH2 + KMnO4/OH
CH2OHCH2OH
Decolourization of bromine water
CH2=CHCH3 + Br2/H2O
CH2CHCH3
Br OH
Catalytic hydrogenation
The addition of hydrogen to the C=C double bond always involves catalysis by such metals as
Ni, Pt at room temperature and pressure.

Ozonolysis of alkenes
Ozone, O3, is highly reactive electrophile. When it is bubbled through a solution of an alkene ,
it reacts with the C=C double bond to yield a five-membered ring . since the O-O-O- is quite
unstable, this intermediate immediately rearranges to give the more stable ozonide. This
ozonide then cleaved with zinc in aqueous acid to form aldehydes or ketones.

Used in the determination of positions of C=C bonds in alkenes


Ozonolysis provides a useful method for determining the position of C=C bonds.
The parent aldene can be reconstructed by recombining the aldehyde or ketone with a double
bond at the carbonyl carbons. For example,

Elimination
alcoholic KOH
(CH3)3C-Br

(CH3)2C=CH2

Polymerization(Free Radical Mechanism)


Alkenes undergo addition polymerization, in which individual monomers are joined together
without the elimination of molecules.
Chain initiation
R+ CH2=CH2
R-CH2 CH2
Chain propagation
R-CH2 CH2 + CH2=CH2
R- (CH2 CH2)n-CH2 CH2 (two eqn. needed for
exam.)
Chain termination
2 R- (CH2 CH2)n-CH2 CH2
R- (CH2 CH2)n-CH2 CH2-CH2 CH2- (CH2 CH2)n- R
Use of Polymer
Low density poly(ethane) is made by the ICI high pressure process. This polymerization takes
place at a high pressure of over 1500atm and a temperature of about 200

You might also like