Alkanes and Their

Stereochemistry

Based on McMurry’s Organic Chemistry, 7th edition

Drawing Organic Structures

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Kekule formula or Expanded structure

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Condensed Structure

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More examples of condensed

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Skeletal or line angle structure

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More examples for skeletal structure

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Activity. Draw the skeletal
structure of the following
1.

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Draw the condensed structures and
indicate their molecular formula

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Alkanes and Alkane Isomers
◼ Alkanes: Compounds with C-C single bonds and C-H
bonds only (no functional groups)
◼ Connecting carbons can lead to large or small molecules
◼ General Formula: CnH2n+2
◼ Alkanes are saturated with hydrogen
◼ They are also called aliphatic compounds

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Cycloalkanes
◼ Cycloalkanes have molecular formula CnH2n
and contain carbon atoms arranged in a ring.

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Straight and Branched-chain

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Classification of Carbons

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Constitutional Isomers
◼ Compounds with the same molecular formula but
different connections between their atoms.

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Isomers
Steps

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Activity
Draw the isomers of the following:

1. Butane
2. Hexane

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Types of Constitutional Isomers
◼ Skeletal

◼ Functional

◼ Positional

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Constitutional Isomers
◼ Different constitutional isomers are completely
different chemical compounds with different
structures, different physical properties, and
potentially different physiological properties.

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Sources of Alkanes:
Fossil Fuels
◼ Natural Gas – composed largely of methane
with lesser amounts of ethane, propane, and
butane used for cooking and heating.

◼ Petroleum – a complex mixture of

hydrocarbons containing 1 – 40 carbon
atoms.
◼ Distilling crude petroleum separates it into
usable fractions that differ in boiling point.

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Three Main Fuels
◼ Gasoline: C5H12 – C12H26
◼ Kerosene: C12H26 – C16H34
◼ Diesel Fuel: C15H32 – C18H38

◼ To increase the amount of gasoline, two

processes are employed
◼ Cracking
◼ Reforming

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Properties of Alkanes
◼ Paraffins (low affinity compounds) because
they do not react as most chemicals

Alkanes are
◼ nonpolar.
◼ insoluble in water.
◼ less dense than water.
◼ flammable in air.

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Properties of Alkanes

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Boiling Point of Alkanes

◼ Alkanes have low bp’s compared to more

polar compounds of comparable size.

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Boiling Point of Alkanes

◼ Bp increases as the number of carbon atoms

increases because of increased surface area

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Boiling Point of Alkanes

◼ Bp of isomers decreases with branching

because of decreased surface area.

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Melting Point of Alkanes

◼ Alkanes have low mp’s compared to more

polar compounds of comparable size.

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Melting Point of Alkanes

◼ Mp increases as the number of carbon atoms

increases because of increased surface area.

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Solubility
◼ Alkanes are soluble in organic solvents.
◼ Alkanes are insoluble in water.
◼ Alkanes have densities of 0.65 – 0.70 g/mL;
floats on water.

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Chemical Properties of Alkanes

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Physical Properties
◼ Boiling points and melting points increase as size of
alkane increases
◼ Dispersion forces increase as molecule size
increases, resulting in higher melting and boiling
points

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Conformations of Ethane
◼ Stereochemistry concerned with the 3-D
aspects of molecules
◼  bonds are cylindrically symmetrical
◼ Rotation is possible around C-C bonds in
open-chain molecules

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Conformers
◼ Conformation- Different arrangement of
atoms resulting rotation around carbon-
carbon sigma bonds.

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Representation of Conformations

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Two Conformations
◼ Eclipsed Conformation
The C – H bonds on one carbon are directly aligned
with the C – H bonds on the adjacent carbon.
◼ Staggered Conformation
The C – H bonds on one carbon bisect the
H – C – H bond angle on the adjacent carbon.

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How to Draw Newman Projection
1. Look directly dwon the C – C bond (end-on),
and draw a circle with a dot in the center to
represent the carbons of the C – C bond.

C in back

= •

C in front

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How to Draw Newman Projection
2. Draw in the bonds. Bonds in front

Bonds in back

Draw the bonds on the front C as three lines meeting at the center of
the circle.
Draw the bonds on the back C as three lines coming out of the edge
of the circle.

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How to Draw Newman Projection
3. Add atoms on each bond.

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Torsional Strain
◼ We do not observe perfectly free rotation
◼ There is a barrier to rotation, and some
conformers are more stable than others
◼ Staggered- most stable: all 6 C-H bonds are
as far away as possible
◼ Eclipsed- least stable: all 6 C-H bonds are as
close as possible to each other

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Activity
◼ Draw the staggered and eclipsed
conformations that result from rotation around
the C– C bond in CH3 – CH2Br.

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Conformations of Other Alkanes
◼ The eclipsed conformer of propane has 3
interactions: two ethane-type H-H interactions, and
one H-CH3 interaction

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 Conformations of Other Alkanes

• Conformational situation is more complex for larger alkanes

• Not all staggered conformations has same energy, and not all
eclipsed conformations have same energy

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Conformations of Butane
◼ Anti conformation- methyl groups are 180˚ apart
◼ Gauche conformation- methyl groups are 60˚ apart

Which is the most energetically stable?

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Steric Strain
◼ Steric strain- repulsive interaction occurring between atoms
that are forced closer together than their atomic radii allow

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Activity
◼ Sight along the C1-C2 bond of 1-
chloropropane, draw Newman projections of
the most stable and least stable conformation.

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Activity

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Answer Key

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