Discussion Topics for Tutorial-1

Lecture 1: Structure and bonding in organic molecules; Newman and Sawhorse Projections;
Conformational analysis of alkanes; Eclipsed, staggered and gauche conformations; Dihedral/
Torsional Angle; Strain in organic compounds – torsional, steric and angle strain; Conformations of
ethane, propane and butane; Gauche conformation stabilization by hyperconjugation and hydrogen
bonding.

Lecture 2: Cycloalkanes, structure, conformations, and ring flipping; Cyclohexane (chair, half-chair,
boat, and twist boat conformations) and monosubstituted-cyclohexane, ring flip, 1,3-diaxial strain,
calculating relative ratio of conformers and Newman projections.

Problems:

1. Write the following compounds in chair conformation and highlight C-C bonds which are in anti-
relationships with each other.

2. Draw the lowest energy chair conformation for each of the following cyclohexane structures.

3. Determine if the highlighted group will appear in the axial or equatorial position in the more stable
chair conformation.
4. Convert the following
a) Newman Projection into a chair conformation,

b) Chair conformation into a Newman Projection

5. Write a more stable conformer in the Newman projection of the following molecules:
a) 1,2-difluoro ethane
b) 1,2-dibromo ethane