Alkanes

-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-

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 ALKANES
• CnH2n+2
• contains only single bonds
• C-C bonds are due to overlapping of sp3orbitals
• saturated hydrocarbons
• C1-4 : gas
• C5-17 : liquid
• C18-more : solid
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EXAMPLE OF ALKANES (STRAIGHT CHAIN)
CH4 methane
C2H6 ethane
C3H8 propane C11H24 undecane
C4H10 butane C12H26 dodecane
C5H12 pentane C13H28 tridecane
C6H14 hexane C14H30 tetradecane
C7H16 heptane C15H32 pentadecane
C8H18 octane
C9H20 nonane
C10H22 decane 4
• Straight-chain hydrocarbons : all of the
carbons are joined in a continuous chain
(straight-chain alkanes are also known as normal (n)
alkanes)
• Branched-chain hydrocarbons: some of
the carbon atoms form a “branch” or side-
chain off of the main chain (possible only
for alkanes containing 4 or more carbons)
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C4H10
Straight-Chain: CH3CH2CH2CH3
Butane
Branched-Chain:
Isobutane

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C5H12
Straight -Chain: CH3CH2CH2CH2CH3

Pentane
Branched-Chain:

2-methylbutane 2,2-dimethylpropane
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 ISOMERS
• meaning made of same parts
• same molecular formula but different
arrangement
Constitutional Isomers
-compounds whose atoms are connected differently
ex. butane and isobutane
pentane and 2-methylbutane and 2,2-dimethylpropane
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 Alkyl Group
-the partial structure when a hydrogen
is removed from an alkane and
becomes a branch of a longer or more
prioritized chain
-named by replacing –ane on alkanes
to -yl
n-alkyl group – formed by removing hydrogen from a
terminal Carbon
branched alkyl group- formed by removing hydrogen from
an internal Carbon (only those containing 3 or more C) 9
 ACTIVITY

Draw and Name the Alkyl Groups

• C2
• C3
• C4
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 ACTIVITY
• Draw three isomers with the formula C8H18
• Draw three isomers with the formula C2H6O
• Draw the eight possible C5 alkyl groups
• Draw an alkane with two 3o carbons
• Draw an alkane with an isopropyl group

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 NOMENCLATURE: NAMING ALKANES
1) Find longest carbon chain (parent chain) (if 2
different longest chains, use one with most
substituents)
2) Number the C atoms in parent chain beginning
from end closest to nearest branch
3) Give alkyl groups attached to the longest chain a
name and a number (locant)
• Multiple alkyl groups named alphabetically
• Multiple groups that are the same: di(2), tri(3),
tetra(4), penta(5), hexa(6) 12
Number Multiplier Number Multiplier
1 mono- 32 dotriaconta-
2 di- 40 tetraconta-
3 tri- 50 pentaconta-
4 tetra- 60 hexaconta-
5 penta- 70 heptaconta-
6 hexa- 80 octaconta-
7 hepta- 90 nonaconta-
8 octa- 100 hecta-
9 nona- 200 dicta-
10 deca- 300 tricta-
11 undeca- 400 tetracta-
12 dodeca- 500 pentacta-
13 trideca- 600 hexacta-
14 tetradeca- 700 heptacta-
15 pentadeca- 800 octacta-
16 hexadeca- 900 nonacta-
17 heptadeca- 1000 kilia-
18 octadeca- 2000 dilia-
19 nonadeca- 3000 trilia-
20 icosa-/eicosa- 4000 tetralia-

21 henicosa-/heneicosa- 5000 pentalia-

22 docosa- 6000 hexalia-

23 tricosa- 7000 heptalia- 13
30 triaconta- 8000 octalia-
PRACTICE

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PROPERTIES & APPLICATIONS OF ALKANES
• little affinity to other substances, inert to most
substances
• non-polar
• Petroleum
• Natural Gas (consist mainly of methane)

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 CONFORMATION
• different arrangement of atoms that result
from bond rotation
• different spatial arrangements that a molecule
can adopt due to rotation about sigma bonds.
Conformational Isomers/ Conformers-
molecules that have different arrangements
( can’t be isolated because it interconvert
rapidly) 16
Representing Conformations:
ex. ethane (C2H6)

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• Staggered - A low energy conformation where
the bonds on adjacent atoms bisect each other
(60o dihedral angle), maximizing the separation.
• Eclipsed - A high energy conformation where the
bonds on adjacent atoms are aligned with each
other (0o dihedral angle). 19
 STRAINS
a molecule experiences strain when its chemical
structure undergoes some stress which raises
its internal energy in comparison to a strain-free
reference compound
Types of Strain
• Steric - Destabilization due to the repulsion
between the electron clouds of atoms or
groups. Groups try to occupy some
common space.
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• Torsional - Destabilization due to the repulsion
between pairs of bonds caused by the
electrostatic repulsion of the electrons in the
bonds. Groups are eclipsed.
• Angle - Destabilization due to distortion of a
bond angle from it's optimum value caused by
the electrostatic repulsion of the electrons in
the bonds. e.g. cyclopropane

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Types of Conformation for adjacent atoms with substituents
Anti - Description given to two substitutents attached to adjacent
atoms when their bonds are at 180o with respect to each other.
Syn - Description given to two substitutents attached to adjacent
atoms when their bonds are at 0o with respect to each other.
Gauche - Description given to two substitutents attached to
adjacent atoms when their bonds are at 60o with respect to each
other. 23
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 CYCLOALKANES
• CnH2
• a ring (closed-chain) hydrocarbon that contains only
single bonds
• only possible for compounds with 3 or more C atoms
• non-polar
• inert to most reagents
• less flexible than open-chain counterparts
• has a top and bottom side
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NOMENCLATURE: NAMING CYCLOALKANES

1) Find parent chain ( alkyl substituted

cycloalkane: ring >= C atoms than in the
substituent or cycloalkyl substituted alkane:
C atoms in a substituent > than in ring)
2) Number the substituents

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PRACTICE

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 ISOMERS
• possible in substituted cycloalkanes
Stereoisomers
-compounds with same atom
connection but different 3D
geometry

Cis-Trans Isomers
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STRAIN

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 CONFORMATION

• Cyclohexane: most abundant cylcoalkane

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Axial & Equatorial Bonds

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