Review

• The carbon of methane (CH4) is sp3 hybridized, making the molecule tetrahedral with
109.5° bond angles
• The carbon and hydrogens are connected through s-bonds, and have a homolytic bond
dissociation energy (BDE) of 105 kcal/mol
• The most common reaction for methane is combustion to form CO2 and H2O and
liberate heat
• The large amount of heat released is due to the high stability of CO2 and H2O and the
instability of O2
• Since all C–H bonds are identical, only one monosubstitution product can be formed
from methane: CH3X, or MeX
• Methane is a low molecular weight hydrocarbon that has only weak dispersion
attractions to itself, making it a gas (natural gas, to be specific)
• Ethane (C2H6) is essentially the product of a union between two methyl groups
• The physical properties of ethane are similar to those of methane
• The carbon–hydrogen bond of ethane has a BDE of 101 kcal/mol, while the C–C bond
has a BDE of 85-90 kcal/mol
• Newman projections represent an end-on view of a bond, and are useful for showing the
relative orientations of substituents on adjacent atoms
• Dihedral angle is defined as the angle between bonds on adjacent atoms
• Two prominent rotational isomers (rotamers) for ethane are the eclipsed conformation
(HCCH dihedral angle is 0°) and the staggered conformation (HCCH dihedral angle is
60°)
• Staggered conformations are lower in energy than eclipsed conformation due to the
avoidance of interactions between the hydrogen atoms (steric interactions)
• The energetic difference between staggered and eclipsed conformations (barrier to
rotation) in ethane is 2.9 kcal/mol, indicating that rotation is rapid at room temperature
• Processes with barriers of <18-20 kcal/mol occur rapidly at room temperature
New material
• Completion of acyclic hydrocarbons

Problem Set 1

Textbook problems
2-19, 2-20, 2-22, 2-25b, 2-26, 2-27, 2-28, 2-30, 2-34, 2-37, 2-39, 2-45, 2-52, 2-53 (8th
Edition)
2-15, 2-16, 2-18, 2-20, 2-21, 2-22, 2-23, 2-25, 2-29, 2-31, 2-33, 2-37, 2-44, 2-45 (7th
Edition)
2-15, 2-16, 2-18, 2-20, 2-21, 2-22, 2-23, 2-25, 2-28, 2-30, 2-32, 2-36, 2-42, 2-43 (6th
Edition)