CH 207 Problem Set #1

1. Draw skeletal and Kekule structures of the following:

a. All isomers with the formula C4H9Br

a. All isomers with the formula C5H11Cl

2. Name all of the above compounds

3. Draw and name all dimethylcyclopropanes, dimethylcyclobutanes, and dimethylcyclopentanes.

4. Name the following compounds:

5. Draw 3 dimensional structures of all cyclohexanes having a methyl and a chloro substituent.

a. Name each of the above structures

b. Label all axial and equatorial substitutents in the above structures

6. Draw Newman projections of the staggered conformations of ethane and chloroethane.

7. Draw 3 dimensional structures of staggered and eclipsed (about the 1,2-bond) of propane and 2-methylpropane.

8. We have said that the difference in energy between staggered and eclipsed propane is about 3.4 kcal/mol. Using energies from your notes and the text, explain why this is so. Which conformer is more stable?

9. Using energies from your notes and the text, estimate the energy difference between the staggered and eclipsed 2-methylbutanes you have drawn above.