Unit III:

Alkanes and Cycloalkanes

E. D. Gloria
UST – Faculty of pharmacy
Chem200 – Organic Chemistry
 Contents
• Different kinds of formulas
– Chemical Formula-writing and Nomenclature of Organic Compounds
• Isomer
• Types of Carbon atoms
• Boiling/Melting points; solubility; Conformations of alkanes
and cycloalkanes
– Sublimation and melting point determination
 Hydrocarbons

Saturated Unsaturated

Alkanes Alkenes Alkynes Arenes

 Isomerism
Existence of compounds with the same molecular formula but
with different chemical and physical properties

Constitutional Isomerism
• Compounds that have the same molecular formula, but
different structural formulas.
Number of Constitutional Isomers
Carbon Atoms Constitutional Isomers
1 0

5 3

10 75

15 4, 347

25 36, 797, 588

 Conformational Isomers
• Isomers having the same connectivity sequence and can be
interconverted by rotation around one or more single bonds.

• Conformation Any three dimensional arrangement of atoms in

a molecule that results by rotation about a single bond.
 Torsional strain
• Eclipsed interaction strain
• Strain that arises when non-bonded atoms separated by three
bonds are forced from a staggered conformation to an eclipsed
conformation.

• The strain due to eclipsing of bonds between neighboring

atoms
 Angle strain
• The strain due to expansion or compression of bond angles
• There are 10 fully eclipsed C-H bonds creating a torsional strain
of approximately 42 kJ>mol (10 kcal/mol). To relieve at least a
part of this
• strain, the atoms of the ring twist into the “envelope”
conformation. In this conformation, four carbon atoms are in a
plane, and the fifth is bent out of the plane, rather like an
envelope with its flap bent upward.
 Steric strain
• the strain due to repulsive interactions when atoms approach
 Geometric isomers
• Is a kind of stereoisomerism wherein two or more compounds
have the same molecular formula but have different
arrangement of the atoms in space.
Draw the structures of the following molecules:
1. trans-1-Bromo-3-methylcyclohexane
2. trans-1-tert-Butyl-2-ethylcyclohexane
3. Cis-1,2-Dimethylcyclobutane