LESSON 2

ALKANES

Overview:
Lesson 2 deals with the structures of alkanes, cycloalkanes, and bicyclic
molecules. The study of organic compounds begins with alkanes because alkane
structures form the hydrocarbon backbones of most organic compounds. Learning to
name organic compounds begins with the names of alkanes because most organic
compounds are named using the parent alkane as the root of the name. The system of
naming chemical compounds, or nomenclature, will be developed and refined throughout
the remaining modules. We will also examine the structures of these compounds and
relate it with their physical properties, including their stable conformations.

Learning Outcomes:
At the end of the exercise, the students should:
1. Draw the structure or isomers of alkanes, cycloalkanes, bicycloalkanes, and alkyl
halides from their names.
2. Name alkanes, cycloalkanes, bicycloalkanes, and alkyl halides with the given
structure.
3. Evaluate the trends in the physical properties of alkanes, cycloalkanes,
bicycloalkanes, and alkyl halides.
4. Predict the most stable conformations of alkanes and cycloalkanes.

Materials Needed:
• Module
• Lecture notebook
• Pen
• Gadgets
• Duration: 3 hours
Learning content:

2.1 CLASSIFICATION OF HYDROCARBONS

• Saturated – a hydrocarbon with no double bonds or triple bonds (ex.

alkanes)
• Unsaturated – a hydrocarbon containing multiple bond (ex. alkenes,
alkynes, arenes)

Alkanes (CnH2n+2)

• aliphatic hydrocarbon that contains only a single bond

• simplest and least reactive than other classes of hydrocarbons
• poor acids and bases, poor electrophiles, and nucleophiles

Ex. General alkanes with molecular formula CnH2n+2.

 2.2 NOMENCLATURE OF ALKANES: IUPAC OR SYSTEMATIC NAMES

International Union of Pure and Applied Chemistry (IUPAC) Rules:

i. The Main Chain: Give the base name of the compound

• Find the longest continuous chain of carbon atoms and use the name of this chain
as the base name of the compound, ending with -ane.
• When there are two longest chains of equal length, use the chain with the greater
number of substituents as the main chain.

ii. Numbering The Main Chain: Give locations of the substituents, assign a number
to each carbon atom in the main chain

• Number the longest chain, beginning with the end of the chain nearest a substituent.
iii. Naming Alkyl Groups: Name the substituent groups

• Name the substituent attached to the longest chain as alkyl groups. Give the location
of each alkyl group by the number of the main-chain carbon atom to which it is
attached.
• Alkyl groups are named by replacing the -ane suffix of the alkane name with -yl.
• Halogen substituents are named fluoro-, chloro-, bromo-, and iodo-.

Ex. Some Common alkyl groups

iv. Organizing The Multiple Groups: Name the compounds with more than one
substituent.
Ex. Nomenclature: IUPAC Names

1. Give the structure of 3-methylhexane and 3-ethyl-6-methylnonane.

Note: Substituents are listed alphabetically (e.g. 3-ethyl-6-methylnonane and NOT 6-

methyl-3-ethylnonane)

2. Give the structures of 4-isopropyloctane and 5-tert-butyldecane.

 2.3 PHYSICAL PROPERTIES OF ALKANES

Solubility:
• Nonpolar (dissolve in nonpolar or weakly polar organic solvents)
• Hydrophobic (“water-hating” - do not dissolve in water)
• Good lubricants and preservatives for metals (keep water from reaching the metal
surface and causing corrosion)

Density:

• Density of around 0.7 g/mL, compared with a density of 1.0 g/mL for water
• Less dense and insoluble in water (a mixture of an alkane (such as gasoline or oil)
and water quickly separates into two phases, with the alkane on top)

Boiling points:

• Boiling points increase with increasing numbers of carbon atoms and increasing
molecular weights
• A branched alkane boils at a lower temperature than the n-alkane (unbranched)
with the same number of carbon atoms

Melting points:

• Melting points increase with increasing molecular weight

• Alkanes with even numbers of carbon atoms pack better into a solid structure, so
higher temperatures are needed to melt them.
• Alkanes with odd numbers of carbon atoms do not pack as well, and they melt at
lower temperatures.

State:
 • 1-4C (gases), 5-17C (colorless liquids), 18 or more C (white, waxy solids)

Physical properties of some simple alkanes.

2.4 PHYSICAL PROPERTIES AND NOMENCLATURE OF CYCLOALKANES

(CnH2n)

Cycloalkanes - contain rings of carbon atoms

Physical properties:

• Nonpolar
• Physical properties are similar to those of the compact, branched alkanes

Physical properties of some simple cycloalkanes.

 Structures of some cycloalkanes.

Nomenclature of Cycloalkanes:

Simple cycloalkanes are named with the prefix cyclo-, indicating the presence of a ring.

i. If there is just one substituent, no numbering is needed.

ii. Numbering begins with one of the substituted ring carbons and continues in
the direction that gives the lowest possible numbers to the other
substituents.
 i. Begin the numbering with the one that has more substituents.

ii. When the acyclic portion of the molecule contains more carbon atoms than
the cyclic portion (or when it contains an important functional group), the
cyclic portion is sometimes named as a cycloalkyl substituent.

2.5 BICYCLIC ALKANES

• Two or more rings joined into bicyclic or polycyclic systems

Nomenclature:
 2.6 ALKYL HALIDES

Three Major Classes:

i. Alkyl halides – has a halogen atom bonded to one of the sp3 hybrid carbon
atoms of an alkyl group

ii. Vinyl halide – has a halogen atom bonded to one of the sp2 hybrid carbon atoms
of an alkene

iii. Aryl halide - has a halogen atom bonded to one of the sp2 hybrid carbon atoms
of an aromatic ring
 2.7 NOMENCLATURE OF ALKYL HALIDES

• For systematic naming of haloalkane:

Fluorine is fluoro-, chlorine is chloro-, bromine is bromo-, and iodine is iodo-.

Ex.

Classification of Alkyl Halides Based on the Nature of Carbon Atom Bonded to

Halogen

i. Primary (1°) halide – halogen-bearing carbon is bonded to one carbon

atom

ii. Secondary (2°) halide – halogen-bearing carbon is bonded to two carbon

atoms
iii. Tertiary (3°) halide – halogen-bearing carbon is bonded to three carbon
atoms

iv. Methyl halide – halogen-bearing atom is bonded to methyl