Hydrocarbon

Hydrocarbons
Unit 13
Or Unit 8
OBJECTIVES:-
Learn about various methods of preparation of
hydrocarbons.
Distinguish between alkanes, alkenes, alkynes on the basis of
physical and chemical properties.
RECALL:-
Homologous series
General formula
Carbon atom is termed as primary (1°), secondary (2°), tertiary
(3°) or quaternary (4°) based upon the number of carbon atoms
attached to a carbon atom.
 Carbon atom attached to no other carbon atom (CH 4) or to only one
carbon atom (CH3-CH3) is called primary carbon atom.
 Carbon atom attached to two carbon atoms is known as secondary.
 Tertiary carbon is attached to three carbon atoms.
 Quaternary carbon is attached to four carbon atoms
ALKANES
Saturated open chain hydrocarbons
Carbon – Carbon single bonds.
Methane (CH4) is the first member of this family.
Known as paraffins as they are inert under normal conditions

and do not react with acids, bases and other reagents.
Preparation:-
1. From unsaturated hydrocarbon
Hydrogenation
 Alkenes and Alkynes
 Dihydrogen gas in the presence of finely divided catalysts like
platinum, palladium or nickel
Q) Convert propene to propane

2. From alkyl halides
a) Reduction
 Alkyl halides (except fluorides)
 Zinc and dilute hydrochloric acid
Q) Convert chloroethane to ethane

Q) Convert bromopropane to propane
b) Wurtz reaction
 Alkyl halides
 Sodium metal ( in dry ether)
 Preparation of higher alkanes containing even

number of carbon atoms.
Q) Convert bromoethane to butane
Q) Prepare octane by Wurtz reaction
3. From carboxylic acids
(i) Decarboxylation
• Sodium salts of carboxylic acids
 soda lime (mixture of sodium hydroxide and calcium
oxide)
 heating
 alkanes containing one carbon atom less than the
carboxylic acid.
(ii) Kolbe’s electrolytic method
 Aqueous solution of sodium or potassium salt of a carboxylic

acid
 Electrolysis
 even number of carbon atoms
Physical properties
 C1 to C4 are gases
 C5 to C17 are liquids
 18 carbon atoms or more are solids
 alkanes insoluble in water
 Petrol and lower fractions of petroleum are also
used for dry cleaning of clothes to remove grease
stains
• As the number of carbon atom increases, the boiling point
increases.
• In the case of isomers, as the branching increases boiling point
decreases. This is because as branching increases, surface area of
contact decreases and van der waal’s force decreases.
• Increase in boiling point with increase in molecular mass

(intermolecular forces increase with increase of the molecular size
(surface area )
Q) Pentane having a straight chain of five carbon atoms has
the highest boiling point (309.1K) compared to
2,2–Dimethylpropane which boils at 282.5K. Justify.
Answer:
 With increase in number of branched chains the molecule
attains the shape of a sphere.
 This results in smaller area of contact therefore, weak
intermolecular forces between spherical molecules which
are overcome at relatively lower temperatures.
HOMEWORK:-
1.What will happen if two different alkyl halides are taken during
Wurtz reaction?
A mixture of three alkanes will be produced. The two alkyl halides
will react with each other forming an alkane. They will also react
among themselves giving two other alkanes.
2.Methane cannot be prepared by Kolbe’s method. Why?

In this method, the alkane is formed by the combination of two
alkyl free radical. Therefore, it would contain atleast two carbon
atoms.
Chemical properties
1. Substitution reactions
(One or more hydrogen atoms of alkanes are replaced by other
groups) eg:-Halogenation
Takes place at higher temperature or in the presence of diffused
sunlight or ultraviolet light.
Chlorination of methane
Fluorination is too violent to be controlled.

Iodination is very slow and is a reversible reaction.
2. Combustion (heating in the presence of air or dioxygen)
Alkanes on complete oxidation forms Carbon dioxide and water
with the evolution of large amount of heat.
Alkanes are used as fuels due to the evolution of large amount

of heat during combustion.
Alkanes on incomplete combustion (insufficient amount of air
or dioxygen) forms carbon black.
It is used in the manufacture of ink, printer ink, black pigments
and as filters.
ALKENES
Geometrical isomerism
Isomers with different geometries i.e.; same structure but
arrangement of atoms or groups in space is different.
• The isomer in which two identical atoms or groups lie on
the same side of the double bond is called cis isomer.
• The isomer in which identical atoms or groups lie on the
opposite sides of the double bond is called trans isomer
cis- But-2-ene trans - But-2-ene
 They differ in their properties like melting point, boiling

point, dipole moment, solubility etc.
Dipole moment
 Cis form of is found to be more polar than the trans form.

 Dipole moment of the trans form is almost zero i.e.; non-polar
 This is because, in the trans-but-2-ene, the two methyl groups are
in opposite directions and dipole moments of C-CH 3 bonds
cancel, thus making the trans form non-polar.
Melting Point
 In the case of solids, the trans isomer has higher melting point
than the cis form. This is due to tightly packed molecules in the
trans isomer.
Q) Cis form has higher boiling point than the trans form.
Give reason
Ans: Because cis form is found to be more polar ( has dipole
moment) whereas transform is non polar(net dipole moment
is equal to zero)
Conditions to show geometrical isomerism
1. It should be an alkene.
2. The two groups attached to one of the double bonded
carbon atom must be different.
Homework
Q) Which of the following compounds show geometrical
isomerism
a)3,4-Dimethylhex-3-ene
b)Hex-2-ene
c)2,3-Dimethylbut-2-ene
d) 4-Methylpent-2-ene
Preparation of Alkene
1. From alkynes
 Alkynes with dihydrogen
 in the presence of partially deactivated palladised charcoal
(Partially deactivated palladised charcoal is known as Lindlar’s
catalyst. )
 Alkenes thus obtained are having cis geometry.
 Trans alkenes are formed on reduction with sodium in liquid
ammonia.
2. From alkyl halides
 Alkyl halides with alcoholic potash (KOH dissolved in alcohol).
 on heating
 dehydrohalogenation occurs. (removal of halogen acid) (one
molecule of halogen acid eliminated)
 β-elimination reaction takes place. (H atom is eliminated from the
β carbon atom i.e.; (C next to the C to which halogen is attached)
Q) What happens when bromopropane is treated with alcoholic potash.

3. From vicinal dihalides
Dihalides in which two halogen atoms are attached to two
adjacent carbon atoms are called vicinal halide.
Eg of Vicinal dihalides
Vicinal dihalides with Zinc metal undergo Dehalogenation.
Q)Convert 1,2-Dibromopropane to propene

4. From alcohols
 Alcohols with concentrated sulphuric acid on heating undergo
acidic dehydration of alcohols (elimination of one water
molecule)
 β-elimination reaction occurs
Q) Prepare propene from propanol

Physical properties
 The first three members are gases
 the next fourteen are liquids
 the higher ones are solids
 Regular increase in boiling point with increase in size.
Straight chain alkenes have higher boiling point than isomeric
branched chain compounds.
Chemical properties
 Alkenes have loosely held ∏ (pi) electrons ∴ they show
addition reactions .
 Alkenes also undergo free radical substitution reactions.
1. Addition of dihydrogen
 in the presence of finely divided nickel, palladium or platinum
to form alkanes.
CH₂= CH₂ + H₂ → CH₃- CH₃

2. Addition of halogens
 Halogens like bromine or chlorine add up to alkene to form vicinal
dihalides.
 Reaction with Br₂
*This reaction is used as a test for unsaturation.
The reddish orange colour of bromine solution in carbon tetrachloride
(Bromine water) disappears when added to an alkene.
3. Addition of hydrogen halides
 HCl / HBr/HI add up to alkenes to form alkyl halides.
 electrophilic addition reaction.
a)Addition of HBr to symmetrical alkenes
b)Addition reaction of HBr to unsymmetrical alkenes

→
Markovnikov rule states that negative part of the addendum

(adding molecule) gets attached to that carbon atom which
possesses lesser number of hydrogen atoms.
Q) What happens when HBr is treated butene
Anti Markovnikov addition or peroxide effect or Kharash effect

In the presence of peroxide, addition of HBr to unsymmetrical
alkenes like propene takes place contrary to the Markovnikov rule.
Q) Peroxide effect is not observed with the addition of HCl, Why?

Ans: HCl bond is stronger than HBr and is not cleaved by the free
radical.
4. Addition of water
 In the presence of a few drops of concentrated sulphuric acid
 form alcohols
 Obeys the Markovnikov rule.
6. Ozonolysis :
• Addition of ozone molecule to alkene to form ozonide, and then
cleavage of the ozonide by Zn-H2O to form smaller molecules.
• Useful in detecting the position of the double bond in alkenes.
Homework
Q)What happens when the following molecules undergo ozonolysis
a) 3,4-Dimethylhept-3-ene
b) 2-Ethylbut-1-ene
Polymerisation:
• Polythene is obtained by the combination of large number of
ethene molecules at high temperature, high pressure and in the
presence of a catalyst.
• Polymers are used for the manufacture of plastic bags, bottles,
radio and TV cabinets etc.

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Hydrocarbons

Saturated open chain hydrocarbons

Carbon – Carbon single bonds.

Methane (CH4) is the first member of this family.

Known as paraffins as they are inert under normal conditions

Q) Convert propene to propane

Q) Convert chloroethane to ethane

 Sodium metal ( in dry ether)

 Preparation of higher alkanes containing even

 Aqueous solution of sodium or potassium salt of a carboxylic

• Increase in boiling point with increase in molecular mass

2.Methane cannot be prepared by Kolbe’s method. Why?

Fluorination is too violent to be controlled.

Alkanes are used as fuels due to the evolution of large amount

cis- But-2-ene trans - But-2-ene

 They differ in their properties like melting point, boiling

 Cis form of is found to be more polar than the trans form.

Q) What happens when bromopropane is treated with alcoholic potash.

Vicinal dihalides with Zinc metal undergo Dehalogenation.

Q)Convert 1,2-Dibromopropane to propene

Q) Prepare propene from propanol

CH₂= CH₂ + H₂ → CH₃- CH₃

a)Addition of HBr to symmetrical alkenes

b)Addition reaction of HBr to unsymmetrical alkenes

Markovnikov rule states that negative part of the addendum

Anti Markovnikov addition or peroxide effect or Kharash effect

Q) Peroxide effect is not observed with the addition of HCl, Why?

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