ALKENES

Dr. Anthoney S. Thangiah,

M.Sc., M.Phil., Ph.D., I.A.C.T
 Nomenclature of Alkenes
• F.G is carbon carbon double bonds.
IUPAC system of nomenclature:

• General formula: CnH2n

• Common names are obtained by changing the ending –ane of the corresponding alkane to –
ylene. (Alkane-ane+ylene)

•IUPAC Rule:
• Select the longest chain containing the double bond. This is the parent chain.
• Name the longest chain (alkane – ane + ene = alkene).
• Number the chain from the end closer to the double bond
• Indicate the position of the double bond by the number of the first (lowest numbered) carbon
atom involved in the double bond.
• Alkyl group and other substituents are numbered, named, and placed as prefixes in
alphabetic order.
• Alkenes contain two double bonds are named as Alkadienes
• In naming CYCLOALKENES, number the ring to give the double bonded carbons the numbers
1 and 2. Choose the direction of numbering so that the substituents get the lowest numbers
(Note: The position of the double bond is not indicated because it is known to be
between C-1 and C-2).
Nomenclature of Alkenes
Nomenclature of Alkene Nomenclature of Alkadiene
 Nomenclature of cycloalkene
Nomenclature of Alkenes
Nomenclature of cycloalkenes
 Write the IUPAC name of the following:
Nomenclature of Alkenes/cycloalkene
 DEGREE OF UNSATURATION
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 DEGREE OF UNSATURATION
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 DEGREE OF UNSATURATION
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 By Dehydration of Alcohols
• When an alcohol is heated in the presence of Con.H2SO4 to give alkene
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with the elimination of a H2O.

By Dehydration of Alcohols
By Dehydration of Alcohols
Saytzeff Rule
 By Dehydrohalogenation of Alkyl halides:
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Note: The ease of dehydrogenation of R-X is: 3⁰>2⁰>1⁰

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By Dehalogenation of Vicinal dihalides
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By Hydrogenation of Alkynes
 By controlled hydrogenation of Alkynes
• Alkynes react with hydrogen in the presence of Lindlar’s catalyst to give
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alkenes.
 By Cracking of Alkanes
• When alkanes heated at 500-600⁰C in the absence of air decompose to
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yield lower molecular weight alkenes, alkanes and hydrogen.

 Physical Properties of Alkenes
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Chemical Properties of Alkenes
 Mechanism of Addition of Carbon-Carbon Double bond ( ):
Chemical Properties of Alkenes
Mechanism of Addition of Carbon-Carbon Double bonds
 1. Addition of Hydrogen
• When achenes react with hydrogen in the presence of Ni, Pd or Pt catalyst under
pressure to give saturated hydrocarbons. A hydrogenation reaction carried in this
Chemical Reaction of Alkenes

manner is called Catalytic Hydrogenation.

Chemical Properties of Alkenes
Addition of Hydrogen
Chemical Properties of Alkenes
2. Addition of Halogen
Addition halogens
Addition halogens
Chemical Properties of Alkenes
3. Addition of Halogen acids:
• Alkenes react with halogen acids (HCl, HBr or HI) to give alkyl halides.
Addition of Halogen acids
 Markovnikov Rule:
• In an addition reaction of a protic acid HX (hydrogen chloride, hydrogen bromide,
or hydrogen iodide) to an alkene or alkyne, the hydrogen atom of HX
Addition of Halogen acids

becomes bonded to the carbon atom that had the greatest number of hydrogen atoms
in the starting alkene or alkyne. [OR]

• When an unsymmetrical reagent adds to an unsymmetrical alkene, the

positive part of the reagent becomes attached to the double bonded
carbon which bears the greatest number of hydrogen atoms.
Addition of Halogen acids Markovnikov Rule:Mechanism
 Antimarkovnikov Rule (Peroxide Effect):
•When an unsymmetrical reagent (H-Br) adds to an unsymmetrical alkene in presence
Addition of Halogen acids

of peroxide, negative part of reagent adds to that carbon of carbon-carbon double bond
which carries more number of hydrogen atoms.
Antimarkovnikov Rule (Peroxide Effect): Mechanism
Antimarkovnikov Rule (Peroxide Effect): Mechanism
 4. Addition of Hypohalous Acids:
• Alkenes react with hypohalous acids, HOX (halogen is the positive part and –OH
group is the negative part) to give halohyrdrins.
• Marknovnikov rule is followed in case of unsymmetrical alkenes
5. Addition of Dil. H2SO4
 6. Alkylation
• Some alkanes add to alkenes in the presence of H2SO4 or HF.
• This reactions is used in the manufacture of isooctane.
7. Hydroboration
8. Oxidation with cold KMnO4 solution
Oxidation with cold KMnO4 solution
9. Oxidation with Hot KMnO4 solution
10. Catalytic Oxidation
11. Ozonolysis
Ozonolysis
Combustion and Polymerization:
14. Substitution of alkenes by Halogens (Allylic Substitution):
Substitution of alkenes by Halogens (Allylic Substitution):
 USES OF ALKENES
• Ethene is used in the manufacture of polyethylene or polythene-a plastic
material.
• Propene is used in the manufacture of polypropene which is used in making
plastic bags, pipes electrical insulation, etc.
• Ethene is used in the preparation of solvents like ethylene glycol, dioxane, etc.
ALKENES

Ethylene glycol is also used as an antifreeze in automobile radiators.

• Ethene is a plant hormone which controls growth, seed germination and fruit
development. Therefore, ethene is used for artificial ripening of fruits, flower
maturation, etc.
• Alkenes are used as a starting material for the manufacture of many
compounds such as alkyl halides, ethylene oxide, ethanol and other alkanols,
etc.
• 1, 3-Butadiene is used in the manufacture of synthetic rubber.
ALKADIENES
 1,3-BUTADIENE
• The most important class of dienes is that of conjugated dienes and
their chemical properties are different from those of ordinary alkenes.
ALKADIENES
ALKADIENES
1,3-BUTADIENE
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1,3-BUTADIENE
1,3-BUTADIENE
Preparation of 1,3-Butadiene
 Preparation of 1,3-Butadiene
(4). Pyrolysis of Cyclo alkenes (Retro Diels-Alder reaction):
1,3-BUTADIENE
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CHEMICAL RXN OF 1,3-BUTADIENE
 Mechanism of 1,2 and 1,4 – Addition Rxn
CHEMICAL RXN OF 1,3-BUTADIENE
 2. Addition of Halogens:
CHEMICAL RXN OF 1,3-BUTADIENE

3. Addition of Hydrogen:

3. Polymerization:
 4. Diels-Alder Reaction
• This reaction takes place between conjugated diene and alkene or an alkyne.
• No catalyst is required for this reaction.
CHEMICAL RXN OF 1,3-BUTADIENE

• Alkene or alkyne in Diels-Alder reactions is referred to as Dienophile (i.e., Diene

lover) and the product is called Adduct.
• During this reaction two new sigma bonds and one new ᴨ bond is formed at the
expense of three ᴨ bonds.
• This reaction is widely used in the synthesis of six membered ring.
• Although the dienophile can be a simple alkene, electron-attracting groups such as
-CN, -CHO, -COR, -COOH, -COOR facilitate the reaction.
Diels-Alder Reaction
Diels-Alder Reaction
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