Alkenes

Definition and Structure of Alkenes

Alkenes are unsaturated hydrocarbons that contain a carbon-carbon double bonds.
Their general formula is CnH2n where n is the number of carbon atoms in the molecule.
Example are:
CH2=CH2 CH2=CHCH3
Ethylene Propylene

Nomenclature of alkenes
IUPAC System
Alkene are named systematically by following a series of rule similar to those developed
for alkanes, with the suffix –ene instead of –ane. Three basic steps are used:

Step 1 Name the parent hydrocarbon. Find the longest carbon chain containing the
double bond, and name the compouns accordingly, using the suffix –ene.
Step 2 Number the carbon atoms in the chain. Beginning at the end nearer the double
bond, assign numbers to the carbon atoms in the chain. If double bond is
equidistant from the two end, begin at the end nearer the first branch point. This
rule assure that the double bond carbons receive the lowest possible numbers
Step 3 Write out the full name. Number the substituents according to their position in the
chain and list the alphabetically. Indicate the position of double bond by giving the
numberof the first alkene carbon. If more than one double bond I present,
indicate the position of each and uses the suffixe –diene, -triene, tetraene and so
on.

6 5 4 3 2 1 H3C 2 3 4 5 6
CH3CH2CH2CH CHCH3 CHCH CHCH2CH3
H3C
1 2-Methyl-3-hexene
2-Hexene

CH3CH2CH2
3 2 1 CH3
C CHCH3 H2C C CH CH2
7 6 5 4 1 2 3 4
CH3CH2CH2CH2
3-Propyl-2-heptene 3-Methyl-1,3-butadiene

IUPAC nomenclature based on newest rule:

Hex-2-ene 3-propylhep-2-ene
2-methylhex-3-ene 3-methylbuta-1,3-diene

Nomenclature of Cycloalkenes
Cycloalkanes are named in a similar way. Always give position 1 to one of the two
carbon at the bouble bond. To decide which carbon gets this number, the ring atoms are
to be numbered from carbon 1 through the double bond in whichever direction reaches a
substituent first. The first branch point has as low a value as possible. For example, the
numbers inside the ring represent the correct numbering, not the numbers outside the
ring
Common Name of Alkenes
The common names are obtained by changing the ending –ane of the corresponding
alkane to –ylene. Example are:
CH 3
CH2=CH2 CH2=CHCH3 H3C C CH2
Ethylene Propylene Isobutylene

Isomers of Alkenes
Alkenes can exist as isomers in any one of three way:
1. They can have different carbon skeletons, as illustrated by 1-butene and 2-
methypropene (chain isomer)
2. They have the same skeletons but differ in locations of their double bonds, as in 1-
butene and 2-butene (position isomer)
3. They can have the same skeletons and the same locations of the double bond, but
they differ in geometry, as in cis-2-Butene and trans-2-Butene (geometrical isomer)

Properties of Alkanes
Physical properties of alkanes
Solubility : Alkenes are insoluble in water, but are soluble in non polar solvents such
as benzene, ether, chloroform, or ligroin
Density : They are less then water
Phase : C2 to C4 are gases, C5-C17 are liquid and >C17 are solid.
Boliling : The boiling point rises with increasing carbon content; as with the
Point alkanes, the boiling point rise is 20-30oC for each added carbon
Chemical Properties
Combustion : Combustion of alkenes produce carbon dioxide and water
(steam) (if enough oxygen with the same coeficient

Addition of : Alkenes react with hydrogen in the presence of Ni (Pt or Pd)

Hydrogen catalyst to form alkanes
(Hydrogenation)

Addition of chlorine : Alkenes react with Cl2 or Br2, usually in carbon tetrachloride
or bromine, but not solution to form dihalides.
iodine
(Halogenation)

Addition of : Alkenes react with HCl, HBr, or HI to form alkylhalides

hydrogen halides Markovnikov Rule
(Hydrohalogenation “When an unsymmetrical reagent adds to an unsymmetrical
) alkene, the positive part of the reagent goes to the double-
bonded carbon that already has the greatest number of
hydrogen atoms”
H adds here
(C has two hydrogens)

CH 3 CH CH 2 Br adds here
(C has one hydrogen)

Anti Markovnikov
This phenomenon of anti-markovnikov addition of HBr
caused by the presence of peroxide is called peroxide effect
CH 3 CH 2 CH 2 Br
Peroxide
n-propyl bromide
(Anti-Markovnikov Product)

CH 3 CH CH 2 + HBr
Br
Propene
CH 3 CH CH 3
Isopropyl bromide
No Peroxide (Markovnikov Product)
Addition of : Alkenes react with hypohalous acids (HOX) to form halohydrins.
hypohalous acids Markovnikov rule is followed in the case of unsymmetrical
alkenes

Addition of : Alkenes react with conc. H2SO4 to form alkyl hydrogen

Sulphuric acids sulphates. Markovnikov rule is followed in the case of
unsymmetrical alkenes. Alkyl hydrogen sulphates on hydrolysis
yield alcohols.
OSO3 H
+ -
H 3 C HC CH 2 + HOSO 3H H 3 C HC CH 3
Propylene Isopropyl hydrogen sulphate

OSO3 H H OH
H3 C HC CH 3 + O H H3 C HC CH 3 + H2SO4
Isopropyl alcohol
(2-Propanol)

Addition of Water : Alkenes react with H2O in the presence of a strong acid (usually
(Hydration) H2SO4) to form alcohols

Oxidation with cold : Alkenes react with dilute cold potassium permanganate solution
dilute KMnO4 to form glycols.
solution
Oxidation with hot : Alkenes react with hot concentrated KMnO4 solution to give
concentrated ketones and/ or acids. Cleavage occurs at the double bond
KMnO4 solution

Ozonolysis : Alkenes react with hot ozone to give aldehydes or ketones or

both of them. Cleavage occurs at the double bond

Preparation of Alkenes
Dehydration of : This involves the treatment of an alcohol with conc. H2SO4. Water
alcohols molecule is eliminated and an alkene is formed

Dehydrohalogenation : This involves the treatment of an alkyl halide with alcoholic KOH or
of alkyl halides NaOH

Partial : This involves the treatment of alkynes with hydrogen in the presence
Hydrogenation of of Lindlar’s catalyst
Alkynes

Alkanes in Nature
Poliethylene (PE), polypropylene (PP) and polyvinylchloride (PVC) are polymers
composed by ethylene, propylene and vinylchloride as monomer.