Conformational Analysis of Cyclohexane The following exercises can be completed using your lecture text as well as your class notes.
1. Draw both forms of the chair conformation of cyclohexane (right and left facing).
2. Draw a chair conformation of cyclohexane with only the axial hydrogen atoms shown.
3. Draw a chair conformation of cyclohexane with only the equatorial hydrogen atoms shown.
4. Draw the process of ring-flip of cyclohexane. Include both chair conformations and the boat conformation.
5. Draw a Newman projection of cyclohexane as viewed down the C1-C2, C5-C4 bonds.
6. Draw methylcyclohexane as a chair structure. Also show the ring-flip conformation of methylcyclohexane. Label each structure as high and low energy.
7. Draw methylcyclohexane using a Newman projection as viewed down the C1-C2, C5-C4 bonds. Show the ring-flip conformation also using a Newman projection. Label each as high or low energy. Indicate any interactions that are present in each structure (gauche, 1,3-diaxial, etc.)
8. Repeat the directions in exercise 7 for cis-1,2-dichlorocyclohexane.
9. Repeat the directions in exercise 7 for trans-1,2-dichlorocyclohexane.
10. Draw trans-1,3-dimethylcyclohexane using a Newman projection as viewed down the C1-C6, C3-C4 bonds. Show the ring-flip conformation also using a Newman projection. Label each as high or low energy. Indicate any interactions that are present in each structure (gauche, 1,3-diaxial, etc.)
11. Draw cis-1,3-dibromocyclohexane using a Newman projection as viewed down the C1-C6, C3-C4 bonds. Show the ring-flip conformation also using a Newman projection. Label each as high or low energy. Indicate any interactions that are present in each structure (gauche, 1,3-diaxial, etc.)
12. Draw trans-1-isopropyl-3-methylcyclohexane using a Newman projection as viewed down the C1-C6, C3-C4 bonds. Show the ring-flip conformation also using a Newman projection. Label each as high or low energy. Indicate any interactions that are present in each structure (gauche, 1,3-diaxial, etc.)
