Alkane and Alkene

Name of Institution
AMITY INSTITUTE OF PHARMACY

B PHARM II SEMESTER
PHARMACEUTICAL ORGANIC CHEMISTRY
Dr PAWAN KUMAR GUPTA
1
Syllabus II- Unit
Name of Institution
UNIT-II Alkanes, Alkenes and Conjugated dienes

• SP3 hybridization in alkanes, Halogenation of alkanes, uses of
paraffins.
• Stabilities of alkenes, SP2 hybridization in alkenes
• E1 and E2 reactions – kinetics, order of reactivity of alkyl
halides, rearrangement of carbocations, Saytzeffs orientation
and evidences. E1 verses E2 reactions, Factors affecting E1 and
E2 reactions.
• Ozonolysis, electrophilic addition reactions of alkenes,
Markownikoff’s orientation, free radical addition reactions of
alkenes, Anti Markownikoff’s orientation.
• Stability of conjugated dienes, Diel-Alder, electrophilic
addition, free radical addition reactions of conjugated dienes,
allylic rearrangement 2
Alkanes, Alkenes and dienesName of Institution
Alkanes
• Alkanes are the Aliphatic hydrocarbons.
• Alkanes are hydrocarbons in which all the bonds are covalent
bonds (-bonds).
• Alkanes are called saturated hydrocarbons.
• The simplest one, methane (CH4), is also the most abundant.
• All carbon atoms are sp3-hybridized
• All bond angles are 109.5
3
Alkyl groups
• Alkyl groups are formed by loss of a hydrogen atom from
the corresponding alkane . General formula of alkyl group :
CnH2n+1
• ( e.g. CH4 Methane – 1 H = -CH3 Methyl group )
• Alkyl groups are named by dropping the -ane suffix of the
alkanes and adding the suffix -yl.
• Methane becomes a methyl group, ethane an ethyl group,
4
etc.
Unbranched alkyl groups
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Nomenclature of branched alkyl groups
•Methyl ethyl is the systematic name; Isopropyl is a

common name.
• Numbering always begins at the point where the group is
attached to the main chain.
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Propane
CH3
CH3-CH2-CH2- CH3 -CH
n-Propyl Isopropyl
Butane
CH3
CH3
H2 H3C C
CH3-CH2-CH2-CH2- CH3 -CH C
CH3
n-Butyl Isobutyl tert.Butyl
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IUPAC nomenclature
• IUPAC (International Union of Pure and Applied Chemistry)
• Identify the longest carbon chain. This chain is called the
parent chain.
• Identify all of the substituents (groups appending from the
parent chain).
• If two or more side chains are in equivalent positions,
assign the lowest number to the one which will come first
in the name.
• If the same substituent occurs more than once, the location
of each point on which the substituent occurs is given.
• In addition, the number of times the substituent group
occurs is indicated by a prefix (di, tri, tetra, etc.).
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• When two or more branched chains are present, give each

branched chain a number corresponding to its position on the
parent chain
• When two or more branched chains are identical, indicate
this by the use of the prefixes ‘di-’, ‘tri-’, ‘tetra-’, and so on
• Select the longest possible straight chain; this gives the parent
name for the alkane
CH3
H
CH3CH2CH2CH2CHCH3 CH3CH2CH2CH2CHCH3 H3C C CH CH2 CH3
CH3 CH2 H2C CH2 CH3
CH3
2- methyl hexane 3- methyl heptane 3,4- dimethyl heptane

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• Number the parent chain beginning with the end of the chain
nearer the branched chain
CH2 CH3
CH3 CH2 CH2 CH CH CH2 CH3
CH3
4-ethyl-3- methyl heptane
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•When two or more substituents are present, give each substituent

a number corresponding to its location on the longest chain.
•When two substituents are present on the same carbon, use

the number twice.
11
• When two or more branched chains are Identical, indicate this
by the use of the prefixes di-,tri-,tetra,and so on.e.g.
•When two chains of equal length compete for selection as the

parent chain, choose the chain with the greater number of
substituents.
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Physical Properties Of Alkanes and Cycloalkanes
• At room temperature ( 25 °C) and 1 atm pressure, the C1-C4
unbranched alkanes are gases; the C5-C17 unbranched alkanes
are liquids; the unbranched alkanes with 18 or more carbon
atoms are solids.
• Boiling Point Higher members have higher boiling points due
to Increase in molecular mass and Increase in intermolecular
force.
• Branched-chain alkanes have lower boiling points than
straight-chain alkanes
• molecule is more compact  surface area 
vander Waals’ force   boiling point 
13
Melting Point Higher members have higher melting points

due to Increase in molecular mass and Increase in
intermolecular force
Solubility Alkanes are non-polar compounds insoluble in water
and highly polar solvents.
• Soluble in non-polar solvents like benzene, 1,1,1-
trichloroethane.
Density All alkanes and cycloalkanes have densities less than
1 g cm–3 at 20°C that is why Petroleum floats on water
surface.
14
Preparation of alkanes
From Alkenes & Alkynes
By Catalytic Hydrogenation
Ni or Pd or Pt / H2
H2C CH2 H3C CH3
200, 300 15
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From alkyl Halides
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By Hydrolysis of Grignard Reagent Grignard reagent is an
alkyl magnesium halide compound, R-Mg-X
• The Grignard reagent is formed when a solution of an Alkyl
Halide (R-X) is allowed to stand over a metallic magnesium in
the presence of dry ether
• Then Grignard reagent react with water or alcohol to form
alkane
19
2+ Dry ether
CH 3CH 2Br + Mg CH 3CH 2MgBr
Grignard reagent
+
H3 O
CH 3CH 2MgBr CH 3CH 3 + Mg(OH)Br
20
By Wurtz reaction
• This is the reaction of two alkyl halides (RX) with metallic
sodium to give symmetrical alkanes
• The wurtz reaction is a poor method for the preparation of
unsymmetrical alkanes.
2 CH3 CH2 CH2 Br + 2 Na CH3 CH2 CH2 CH2 CH2 CH3
+ 2 NaBr 21
Reactions of Alkanes
• Combustion Alkanes react with sufficient oxygen to give
carbon dioxide and water through a complex series of reaction
with the release of a large amount of energy.
 3n  1 
C n H 2 n 2    nCO 2  n  1H 2O
O 2 
 2 
complete combustion
Incomplete combustion
CH3-CH2-CH3 + 4 O2 ——> CO2 + 2 CO + 4 H2O + heat 22
Halogenation of Alkanes (Free Radical Substitution
Reaction)
• A free radical may be defined as an atom or group of atoms
having an unpaired electron.
• Free radicals are produced during the homolytic fission of a
covalent bond.
• Free radicals are very reactive as they have strong tendency to
pair up their unpaired electron with another electron from
wherever available.
• These pairs are very short lived and occur only as reaction
intermediates during reactions.
• For example, dissociation of chlorine gas in the presence of
ultra-violet light produces chlorine free radicals:
23
• The alkyl free radical may be obtained when free radical
chlorine attacks methane.
• Free radicals may be classified as primary, secondary or

tertiary depending upon whether one, two or three carbon
atoms are attached to the carbon atom carrying the odd
electron:
24
• The reaction of a halogen with an alkane in the presence of

ultraviolet (UV) light or heat leads to the formation of a
haloalkane (alkyl halide).
• An example is the chlorination of methane.
• Halogenation of Alkanes is an Free Radical Substitution
Reaction
25
Summary:
• When treated with Br2 or Cl2, Free radical substitution of
R-H generates the alkyl halide and HX.
• Alkane (R-H) relative reactivity order is
tertiary > secondary > primary > methyl.
• Halogen reactivity is
F2 > Cl2 > Br2 > I2.
• Only chlorination and bromination are useful in the
laboratory.
• Bromination is selective for the R-H that gives the most
stable radical.
• Chlorination is less selective
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Inhibitors
• Inhibitor - a substance which slows down or stops a
reaction even though the present in small amounts.
• Inhibition period - time during which the inhibitor lasts.
• Example: If oxygen is present during halogenation, the
oxygen slows down the reaction.
• This breaks the cycle (propagating steps) and slows down
the reaction.
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Uses of Paraffin
• Paraffin more commonly referred to as alkanes, are the
chemical family of saturated hydrocarbons.
• The general formula CnH2n+2.
• The paraffin are major constituents of natural gas and
petroleum.
• Paraffin containing fewer than 5 carbon atoms per molecule
are usually gaseous at room temperature, those having 5 to 15
carbon atoms are usually liquids, and the straight-chain
paraffins having more than 15 carbon atoms per molecule are
solids.
• The hydrocarbons are immiscible with water.
• All paraffin‟s are colourless.
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• Paraffin is a strong-smelling liquid which is used as a fuel in

heaters, lamps, and engines
• Medicinal liquid paraffin, also known as paraffinum liquidum,
is a very highly refined mineral oil used in cosmetics and for
medical purposes.
• Liquid paraffin has many uses in the medical field.
• Because liquid paraffin passes through the body's intestinal
tract without being absorbed, it can be used as a laxative and
ease constipation.
• Liquid paraffin will reveal that this common personal care
ingredient is used in many skin products, including creams,
lotions, lip balm, soap, and even eczema ointments.
. 30
• In burns treatment that involved covering the affected area
with a combination of waxes and oils including paraffin wax
use for the skin to heal and was seen as a very effective
treatment
• Paraffin wax were developed, the most popular of which was
giving hot wax baths to patients suffering from a variety of
ailments, in particular rheumatism and joint pain.
• White soft paraffin with liquid paraffin is used as a barrier
cream by providing a layer of oil on the surface of the skin to
prevent water evaporating from the skin surface.
• It is an emollient, sometimes known as skin lubricant. It is
used to soothe, smooth and hydrate the skin.
31
Alkenes
• They are organic compounds containing double bonds in their
chemical structure.
• They are known as olefins.
• Alkenes are class of unsaturated hydrocarbons containing
carbon and hydrogen atoms having one or more carbon-carbon
double bonds in its chemical structure.
• The unsaturation is because of the presence of one or more
double bonds in its structure.
• The general formula of the homologous series of hydrocarbon
is CnH2n.
• general chemical structure of alkene is RC=CR’.
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• Hence, alkene contains 2 hydrogen atoms less than its
corresponding alkane.
• Ethylene having the formula C2H4 is the simplest alkene.
Nomenclature of alkenes
• Nomenclature or naming alkenes is very similar to alkanes
according to the IUPAC system.
• We have to select the longest chain of carbon atoms having the
double bond in order to name an alkene according to the
IUPAC system.
• We start numbering from the carbon chain near to the double
bond. “Ene” replaces “ane” suffix present in the alkanes.
• The first stable compound is ethylene or ethene (C2H4).
33
Preparation of Alkenes
• Alkenes are usually prepared from either alcohols or alkyl
halides.
By the dehydration of alcohols
• Alkenes are obtained by the dehydration of alcohols.
• The dehydration of alcohols can be affected by two common
methods.
• By passing the vapors of an alcohol over heated alumina.
• By heating an alcohol with concentrated mineral acid, such as
concentrated H2SO4 or concentrated H3PO4·
• Anhydrous zinc chloride can also be used as a dehydrating
agent.
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• By passing the vapors of an alcohol over alumina (Al2O3) at
350°c.
•The order of the ease of dehydration of alcohols is, tertiary >

secondary > primary
•Secondary and tertiary alcohols are best dehydrated by dilute
sulphuric acid. 35
From haloalkanes (or, alkyl halides)
• Alkenes can be obtained from haloalkanes (alkyl halides).
These haloalkanes are usually bromo and iodo and less
commonly, chloro derivatives.
• Haloalkanes on heating with alcoholic potash loses one
molecule of potassium halide to give alkene.
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• If two alkenes may be formed due to dehydrohalogenation of a
haloalkane, the one which is most substituted is the main
product.
• For example, dehydrohalogenation of 2-bromobutane gives,
37
From carboxylates: By Kolbe's electrolytic method
• Sodium or potassium salt of a dicarboxylic acid on electrolysis
gives an alkene.
• When an aqueous solution of sodium or potassium salt of a
dibasic acid is electrolyzed, an alkene is produced.
• For example, electrolysis of sodium succinate gives ethene
At anode
At Cathode
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From alkynes
•Alkenes can be easily obtained by hydrogenation of alkynes.
•Alkynes on controlled hydrogenation with hydrogen in the
presence of Ni or Pd at 200°C give corresponding alkene.
Ethyne gives ethene on hydrogenation.
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Name of Institution

AMITY INSTITUTE OF PHARMACY

UNIT-II Alkanes, Alkenes and Conjugated dienes

•Methyl ethyl is the systematic name; Isopropyl is a

CH3-CH2-CH2- CH3 -CH

• When two or more branched chains are present, give each

CH3 CH2 H2C CH2 CH3

2- methyl hexane 3- methyl heptane 3,4- dimethyl heptane

CH3 CH2 CH2 CH CH CH2 CH3

•When two or more substituents are present, give each substituent

•When two substituents are present on the same carbon, use

•When two chains of equal length compete for selection as the

Melting Point Higher members have higher melting points

2 CH3 CH2 CH2 Br + 2 Na CH3 CH2 CH2 CH2 CH2 CH3

• Free radicals may be classified as primary, secondary or

• The reaction of a halogen with an alkane in the presence of

• Paraffin is a strong-smelling liquid which is used as a fuel in

•The order of the ease of dehydration of alcohols is, tertiary >

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