Alkanes, Alkenes And Conjugated

Dines
 POINTS TO BE COVERED

• Introduction

• Alkanes

• Alkene

• Hybridization of Alkanes

• Parabens

• Hybridization of Alkene

• E1 E2 reactions

• Conjugated dienes
HYDROCARBONS

A compound composed of only Carbon and Hydrogen

Hydrocarbons

Aliphatic Aromatic

Alkane Alkene Alkyne

ALKANES

• Simplest class of organic compounds.

• Made of Carbon and Hydrogen atoms only
• Two type of bonds, carbon-hydrogen (C-H) and carbon-carbon (C-C) single
covalent bonds.
• No functional groups.
• Also called
• Saturated hydrocarbons.
• Aliphatic compounds
• Paraffins
ALKANES

CnH2n+2 where n: 1,2,3,4….

TYPES OF CARBON

Primary carbon - 1º => Attach to 1 or no. of carbons

Secondary carbon - 2º => Attach to 2 other carbons
Tertiary carbon - 3º => Attach to 3 other carbons
Quaternary carbon - 4º => Attach to 4 other carbons
ALKYL GROUP

The Alkane group is a formate by removable of one hydrogen atoms from alkane

Ex: -H
R-H R (R= ALKYL GROUP)

-H
CH3-H CH3
METHYL
 USES OF ALKANES

• Methane ,ethane, propane and butane are used for heating, cooking and electricity
generations
• Methane and ethane are natural gases- fuel and good solvents
• Above 17 carbon atoms alkane are the main components of lubricants oil and fuel oil.
• Many solid alkanes uses as paraffin wax.
• Ethane is used as refrigerator systems. Its manufacture of plastic, automotive antifreeze
and detergents.
• Pentane is active ingredient of pesticides and also used as liquid chromatography.
• Hexane is used for leather products and shoes.
• Heptane is used in paints
• Halothane is used as general anesthetics.
M E T H O D O F P R E PA R AT I O N O F A L K A N E S

 HYDROGENATION OF ALKENES AND ALKYNES

 REDUCTION OF ALKYL HALIDES

 DECARBOXYLATION OF CARBOXYLIC ACID

 HYDROLYSIS OF GIRNARD REAGENTS

 WURTZ SYNTHESIS

 COREY- HOUSE ALKANE SYNTHESIS

 KOLBE’S ELECTROLYSIS METHOD

H Y D R O G E N AT I O N O F A L K E N E S A N D A L K Y N E S

Alkanes can be prepared by the catalytic hydrogenation of unsaturated hydrocarbons in the presence of catalyst ‘Ni’ or
‘Pt’ at high temperature of 200oC to 300oC
RE DUC TI ON OF A L K Y L HA L IDE S
D E C A R B O X Y L AT I O N O F C A R B O X Y L I C A C I D
H Y D R O LY S I S O F G I R N A R D R E A G E N T S
WURTZ SYNTHESIS
C O R E Y- H O U S E A L K A N E S Y N T H E S I S
K O L B E ’ S E L E C T R O LY S I S M E T H O D
REACTION OF ALKANES

 Halogenation

 Nitration

 Sulphonation

 Isomerisation

 Pyrolysis

 Aromatization
H A L O G E N AT I O N

• Bromination, Iodination, Fluorination

• Methane reacts with Chlorine in the presence of UV or at high Temperature
(300 deg C) to yield Methyl Chloride or chloromethane and hydrogen chloride
 N I T R AT I O N

Nitric acid has no action on lower alkanes but by its long, continued action on higher hydrocarbons one of their hydrogen
atoms may be replaced by a nitro-group.

For example, when hexane is heated with fuming nitric acid for forty hours, about ten per cent of the hydrocarbon is
converted to NITROHEXANE
S U L P H O N AT I O N

Alkanes react with fuming sulphuric acid at elevated temperatures to produce alkanesulphonic acids.
I S O M E R I Z AT I O N

n-Alkanes in the presence of aluminium chloride and hydrogen chloride or

of aluminium bromide and hydrogen bromide are converted to their
branched·chain isomers.

Isomerisation of alkanes is of considerable importance in the petroleum industry.

P Y R O LY S I S

When the vapors of a higher alkane are heated at elevated temperature

(500° or more) in the absence of oxygen, chemical decomposition occurs in
two ways:
(i) by fission of C-H linkages to form an unsaturated hydro carbon and
hydrogen gas ; and
(ii) by fission of C-C linkages to give simpler hydrocarbons - one alkane and
one alkene.
A R O M AT I Z AT I O N

n-hexane and n-heptane when passed over Cr2O3 supported on Al2O3 at 600deg, yield Benzene and
toluene respectively.
ALKENES

• Made up of carbon and hydrogen atoms only and contains carbon-carbon (C=C)
double bonds.
• No functional groups.
• Unsaturated hydrocarbons.
• Alkenes another name is olefins (oil forming)
• Suffix “-ene”
ALKENES

The general formula of alkene is CnH2n where n: 1,2,3,4….

P H Y S I C A L P R O P E RT Y

C1-C4 gases
C5-C18 liquids
More than C18 solids

Alkenes are nonpolar compounds. Thus alkenes are soluble in the nonpolar
solvents such as carbon tetrachloride (CCl4) and benzene (C6H6), but they are
insoluble in polar solvents such as water.
USES

•Alkenes are used in manufacturing of plastic.

•These are used as raw material for the manufacture of industrial chemicalslike

alcohols, aldehyde etc.

•Used as general anaesthetics

•Propene used in synthesis of vinegar, propanol, and glycerine, acetone, phenol

etc,

•Its production of other chemical

C O M PA R E

Alkanes Alkenes

Name ends in -ane Name ends in -ene

Only one single Carbon- Carbon Have at least one Carbon – Carbon
bond double bond

Saturated molecules Unsaturated molecules

General formula CnH2n+2 General Formula CnH2n

Undergo Substitution reaction Under go Addition reaction

Do not react with bromine water Do react with Bromine water Orange
to color less

Burns with Clean flame Burns with smoky flames

Useful as fuel Useful for making polymers

M E T H O D O F P R E PA R AT I O N O F A L K E N E S

 Dehydration of Alcohols

 Dehydrohalogenation of Alkyl Halides

 Dehalogenation of Dihaloalkanes

 Partial hydrogenation of Alkynes

 Cracking
 D E H Y D R AT I O N O F A L C O H O L S
 D E H Y D R O H A L O G E N AT I O N O F A L K Y L H A L I D E S
SAYTZEFF Rule
 D E H A L O G E N AT I O N O F D I H A L O A L K A N E S

When dihalogen derivatives of alkenes having the two halogen atoms on adjacent carbons are heated with an active metal
like Zinc the latter removes the halogen atoms to form alkenes.
 PA R T I A L H Y D R O G E N AT I O N O F A L K Y N E S
CRACKING

The higher alkanes when heated to a high temperature decompose to give a lower alkene.
S TA B I L I T Y O F A L K E N E S

• Tetra substituted Alkenes are more stable than Tri, Di, mono Substituted Alkenes
• In Di substituted Alkenes, Trans form is more stable than Cis form
• More Substitution leads to more Conjugation, more conjugation directly proportional to Stability.
• Less Stable isomer has higher energy which is identified by heat of hydrogenation
• e.g. Cis 2-butene exerts -2. kcal/mole energy while trans 2-butene exerts -27. kcal/mole energy
on hydrogenation of 2-butene
REACTION OF ALKENES

• Addition of Hydrogen
• Addition on Halogen
• Addition of Halogen Acid (HX)
• Addition of Sulphuric Acid
• Addition of Water
• Ozonolysis
• Oxidation (Visual Test of Unsaturation)
• Polymerization
• ADDITION OF HYDROGEN
• ADDITION ON HALOGEN
• ADDITION OF HALOGEN ACID (HX)
MARKOVNIKOV’SRULE

 In, 1989 russian scientist morkonikov discovered this reaction

Mechanism:
Step:1
Proton adds on the terminal carbon atom of double bond the secondary carbocation is formed.
CH3 CH CH2 + H+ CH3 CH+ CH3
prop-1-ene
Br-

H
CH3 C CH3

Br
major

Step-2:
Addition of protons occurs on the middle carbon atom then primary carbocation is formed.

CH3 CH CH2 + H+ CH3 CH+ CH3

prop-1-ene
Br-

CH3 CH2 CH2 Br

minor
 known as “ kharash effect/ peroxide effect.
Anti Markovnikov’sRule

•Peroxide effect is observed with HBr only and

not with HCl, HF, and HI.
• ADDITION IF SULPHURIC ACID
• A D D I T I O N O F WAT E R
• O Z O N O LY S I S

Passing Ozone through a solution of an alkene in an inert solvent like CHCl 3 like at low
temperatures it reacts by addition across the carbon –carbon double bond of the alkene.
First an unstable intermediate monozonide is formed which spontaneously isomerizes to give the
ozonide.
Ozonide decompose in presence of zinc to form carbonyl compound.
O X I D AT I O N
O X I D AT I O N
• P O LY M E R I Z A T I O N

At high temperature and in the presence of acid catalyst Alkene molecules add to one
another to form polymers.
 NEXT LECTURE

• Elimination Reaction E1 and E2

• Hybridization of Alkanes an Alkenes
• Conjugated dienes