13.

Hydrocarbons

Classification:
Saturated Single bond
Unsaturated Multiple bond
Aromatic

Alkanes:
General formula is CnH2n+2.
Structural isomer Difference in structure
Chain isomer Difference in chain

Preparation
 From unsaturated hydrocarbons (hydrogenation)
Pt/Pd/Ni
CH3 CH=CH2 H2 CH3 CH2 CH3
 Wurtz reaction (Preparation of higher alkanes containing even number
of carbon atoms)
dry ether
CH3Br 2Na BrCH3 CH3 CH3 2NaBr
 De-carboxylation (Elimination of carbon dioxide from carboxylic acid)
CaO
CH3COONa NaOH CH4 Na 2CO3

Physical properties
 Boiling point increases with increase in molecular mass. Further, it
decreases with increase in number of branched chains.

Chemical properties
 KMnO4 can oxidise alkanes having tertiary H atoms to corresponding
alcohols.
KMnO4
CH3 3 CH Oxidation
CH3 3 COH

 Aromatization

 Pyrolysis or cracking
 Conformations
 Sawhorse projections

 Newman projections

Alkenes:
General formula is CnH2n.

Position isomer
1 2 3 4 5
C H2 = C H C H 2 C H 2 C H3
Pent-1-ene
1 2 3 4 5
C H 3 C H= C H C H 2 C H 3
Pent-2-ene

Geometrical isomerism
 Preparation
 From alkynes

Pd/C Lindlar’s catalyst

 From alkyl halides (Dehydrohalogenation)

Physical properties
 Boiling point decreases with increase in number of branched chains.

Chemical properties
 Addition of HBr to unsymmetrical alkenes (Markovnikov rule)
CH3 CH=CH 2 HBr CH3 C H CH3
|
Br
 Anti-Markovnikov addition (Peroxide effect or Kharash effect)
C6 H5CO 2 O2
CH3 CH=CH2 HBr CH3 CH2 CH2Br

 Ozonolysis

Alkynes:
General formula is CnH2n–2.
Preparation
  From vicinal dihalide

Physical properties
 All alkynes are colourless.
 Melting point, boiling point, and density increase with increase in molar
mass.

Chemical properties
 Acidic character
HC ≡ CH > H2C=CH2 > CH3–CH3
HC ≡ CH > CH3–C ≡ CH >> CH3–C ≡ C–CH3

 Addition of hydrogen
Pt/Pd/Ni H2
HC CH H 2 H 2C=CH 2 CH3 CH3

 Cyclic polymerization

Aromatic hydrocarbon:

Aromaticity
 Planarity
 Complete delocalization of the electrons in the ring
 Huckel rule Presence of (4n + 2) electrons in the ring (n = 0, 1,
2…)

Preparation of benzene
 Cyclic polymerization of ethyne
 Decarboxylation of aromatic acids
Physical properties
 Immiscible with water but readily miscible with organic solvents

Chemical properties
 Electrophilic substitution
 Nitration

 Halogenation

 Friedel-Crafts alkylation

 Friedel-Crafts acylation

 On treatment with excess of chlorine

 Addition reaction
 Directive influence of functional group in benzene ring
 Ortho and para directing groups:
–OH, –NH2, –NHR, –NHCOCH3, –OCH3, –CH3, –C2H5
 Meta directing groups:
–NO2, –CN, –CHO, –COR, –COOH, –COOR, –SO3H

Carcinogenicity and toxicity

Benzene and polynuclear hydrocarbons containing more than two benzene rings
are toxic and can cause cancer.

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