Question

There are four cis,trans isomers for 3-tert-butyl-5-methylcyclohexanol, where the cis,trans designations of the substituents are made relative to the OH group:

up, up, up (cis,cis)
up, up, down (cis,trans)
up, down, down (trans,cis)
up, down, up (trans,trans)
Consider the most stable chair for each of these isomers, and then draw the most stable and least stable isomer based on a comparison of the best chair for each one.

- To simplify matters, consider only axial vs equatorial energies of the groups (i.e. do not worry about the interactions between the groups, which in reality is also important).
- Use the wedge/hash bond tools to indicate stereochemistry where it exists.
- You do not have to explicitly draw H atoms.
- Use “flat” representations of rings, not chairs, in your drawing.

WHAT IS LEAST AND MOST STABLE?

PLEASE DRAW

Answer 1