BAZE UNIVERSITY, ABUJA

FACULTY OF COMPUTING AND APPLIED SCIENCES

MODULE: GENERAL CHEMISTRY II

TOPIC: ALKANES AND CYCLOALKANES

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 QUIZ
Review of Previous Class
⚫ Write the state of hybridisation of carbon in the following compounds and shapes
of each of the molecules.
(a) H2C=O
(b) (b) CH3F
(c) (c) HC≡N

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⚫ ALKANES
Alkanes are hydrocarbons i.e. compounds made of carbon and hydrogen only. There are
two kinds of alkanes-linear and cyclic alkanes or cycloalkanes.
The linear alkanes have the general formula CnH2n+2
CnH2n+2 n=1, CH4
n=2, C2H6
n=3, C3H8
n=4, C4H10

C2H6 ethane

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 ⚫ cycloalkanes have the general formula CnH2n.
Other forms of cycloalkanes include: bicyclic and tricyclic cycloalkanes
with bridges containing any or no carbon atom.
⚫ Another special class of cycloalkanes is the so called spiroalkanes, which
have one carbon atom common between two rings.

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 Nomenclature
Alkanes are usually referred by their trivial names. However, the IUPAC
lays down certain rules for the nomenclature of alkanes
hexanes C6H14

CH3
CH3CH2CH2CH2CH2CH3 CH3CHCH2CH2CH3
n-hexane isohexane

CH3
CH3CCH2CH3
CH3
neohexane

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 IUPAC rules for naming alkanes:
Rule 1. The name of an alkane consists of two parts- a prefix and a root. The
prefix will denote the number of carbons present in the chain.
⚫ The moiety generated by removing a hydrogen from an alkane is called an
alkyl group

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 Number of Carbons IUPAC Name of Name of Moiety
Prefix Hydrocarbon Generated by Removing a
Hydrogen
1 Meth Methane (CH4) Methyl(CH3)

2 Eth Ethane (C2H6) Ethyl( C2H5)

3 Prop Propane ( C3H8) Propyl(C3H7)

4 But Butane (C4H10) Butyl(C4H9)

5 Pent Pentane (C5H12) Pentyl( C5H11)

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Rule 2. In case of cycloalkanes, the word cyclo should be prefixed with the name of
alkane. Thus, a cycloalkane containing three carbon atoms is called cyclopropane.

Cyclopropane Cyclohexane Cycloheptane

1-Ethyl-3-methylcyclopentane

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Example
Name these compounds:

a) This compound is methylcyclopentane. No number is needed

c)We get the lowest numbers only by starting at the position with two bromines.
The correct name is 1,1,3,6- tetrabromocyclooctane

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⚫ Rule 3. In case of branched alkanes, the longest carbon chain gives the name
of the parent alkane. The substituents are to be prefixed using suitable locants.
If there are multiple same substitutents, then the prefixes di-, tri, tetra- etc are
added before the substituent name.

2,7,8-trimethyldecane
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 If there is more than one type of substituents, then they are usually arranged
in an alphabetical order. Thus, in the compound below , ethyl group is
mentioned before the methyl groups.

3-ethyl-2,2,3-trimethylheptane

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 ⚫ If more than one substituent is attached to the parent hydrocarbon, the chain
is numbered in that direction that will result in the lowest number in the
name of the compound (Rule of lowest locants).

5-ethyl-3-methyloctane but not

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 Isomerism
⚫ The phenomenon of existence of two or more compounds possessing the same
molecular formula but different properties is known as isomerism.
Structural Isomerism
⚫ Compounds having the same molecular formula but different structures. Some typical
examples of different types of structural isomerism are given below:
⚫ (i) Chain isomerism: When two or more compounds have similar molecular formula
but different carbon skeletons, these are referred to as chain isomers and the
phenomenon is termed as chain isomerism. For example, C5H12 represents three
compounds:

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(ii) Position isomerism: When two or more compounds differ in the position of
substituent atom or functional group on the carbon skeleton, they are called position
isomers and this phenomenon is termed as position isomerism. For example, the
molecular formula C3H8O represents two alcohols:

(iii) Functional group isomerism: Two or more compounds having the same molecular
formula but different functional groups are called functional isomers and this
phenomenon is termed as functional group isomerism. For example, the
molecularformula C3H6O represents an aldehyde and a ketone:

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 ⚫ Stereoisomerism: The compounds that have the same constitution and
sequence of covalent bonds but differ in relative positions of their atoms
or groups in space are called stereoisomers.This special type of isomerism
is called as stereoisomerism and can be classified as geometrical and
optical isomerism.

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 Butane and all succeeding alkanes exhibit structural isomerism
Two isomers of butane C4H10:
CH3CH2CH2CH3 n-butane

CH3
CH3CHCH3 isobutane

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 The Isomeric Hexanes, C6H14
⚫ The five isomeric hexanes have the structures

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 Alkanes and number of isomers
Alkane name isomers
CH4 methane 1
C2H6 ethane 1
C3H8 propane 1
C4H10 butanes 2
C5H12 pentanes 3
C6H14 hexanes 5
C7H16 heptanes 9
C8H18 octanes 18
C9H20 nonanes 35
C10H22 decanes 75
C20H42 eicosanes 366,319

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⚫ Carbon atoms in alkanes are sometimes labeled as primary (1°), secondary (2°) and
tertiary (3°) carbon. This classification is based on the number of carbon atoms
attached to the carbon atom.
⚫ If a carbon atom is attached to one carbon atom, then it is called a primary carbon.
⚫ A carbon atom which is attached to two carbon atoms is called secondary carbon
⚫ three other carbon atoms = tertiary carbon.

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 STEREOISOMERISM IN CYCLIC COMPOUNDS
⚫ Rotation around the bonds in a cyclic structure is limited by the fact that the
carbons of the ring are all bonded to another carbon within the ring. The
formation of cis-trans isomers, or geometric isomers, is a consequence of the
absence of free rotation
⚫ Compounds that have the same structural formulas but different three
dimensional shapes (cannot be superimposed) are called stereoisomers
⚫ Cis =the same side
⚫ trans = opposite sides:

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 Physical Properties of Alkanes
⚫ physical state changes from gas to liquid to solid as the molecular weight
increases.
⚫ Branching leads to lower boiling points
⚫ non-polar, hence insoluble in water.

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 Preparation of Alkanes
⚫ The principal source of alkanes is naturally occurring petroleum and gas
⚫ important constituents obtained by fractional distillation of petroleum are listed
belowNames of Fraction Carbon Atoms Present Boiling Range (°C) Use

Fuel gas, LPG 1-4 <25 Used as fuel for domestic purposes

Petrol 5-7 25-75 Fuel for light automobiles

Naphtha 6-10 75-190 Feedstock for cracking

Kerosene 10-16 190-250 Domestic fuel, Air turbine fuel

Diesel 14-20 250-350 Fuel for heavy automobiles

Residue (Fuel oil, lubricating oil, waxes) 20-70 >350 Used as lubricating agents for machinery

Asphalt Over 70 Non volatile Used on roads

⚫ Reaction of alkyl halides (except fluorides) with zinc and dilute hydrochloric
acid give alkanes

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 CHEMICAL PROPERTIES OF ALKANES
⚫ Combustion
All alkanes burn readily in air to give CO2 and H2O in very exothermic reactions.
This is of course the reason they are widely used as fuels.

⚫ Substitution Reaction with Halogens

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 OTHER REACTIONS OF ALKANES
⚫ Pyrolysis( Thermal or Catalytic cracking):

⚫ Isomerization:

⚫ Cyclization

⚫ Aromatization:

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 Exercise
Name the following compounds by the IUPAC system:
1.

2.

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 3.

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