4. Alkanes and Cycloalkanes

Draw 1,2,3,4,5,6-hexachlorocyclohexane with

a. all the chloro groups in axial positions.

b. all the chloro groups in equatorial positions.

In the lowest energy chair conformation of $\mathrm{methylcyclohexane}$, how many methyl groups are in the axial position?

Draw 1,2,3,4,5,6-hexamethylcyclohexane with all the methyl groups

a. in axial positions.

For each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformers are both equatorial in one chair conformer and both axial in the other or one equatorial and one axial in each of the chair conformers:

a. cis-1,2-

b. trans-1,2-

Draw 1,2,3,4,5,6-hexamethylcyclohexane with all the methyl groups

b. in equatorial positions.

Which of the following best describes the orientation of axial bonds in a chair conformation of $\mathrm{cyclohexane}$?

This is a Newman projection of a substituted cyclohexane.

b. Draw the equivalent structure using wedge and dash notation on a cyclohexane hexagon.

This is a Newman projection of a substituted cyclohexane. a. Draw the equivalent chair form.

Draw the two chair conformers for each of the stereoisomers of trans-1-tert-butyl-3-methylcyclohexane.

For each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformers are both equatorial in one chair conformer and both axial in the other or one equatorial and one axial in each of the chair conformers:

e. cis-1,4-

f. trans-1,4-

a. Draw Newman projections of the two conformers of trans-1,3-dimethylcyclohexane.

b. Which of the conformers predominates at equilibrium?

This is a Newman projection of a substituted cyclohexane.

c. Give the IUPAC name.

For each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformers are both equatorial in one chair conformer and both axial in the other or one equatorial and one axial in each of the chair conformers:

c. cis-1,3-

d. trans-1,3-