How to Draw chairs
Most of the structures shown on this page were drawn with the free program ISIS/Draw. I have posted a guide to help you get started with ISIS/Draw. ISIS/Draw provides a simple cyclohexane (6-ring) hexagon template on the toolbar across the top. It provides templates for various 6-ring chair structures from the Templates menu; choose Rings. There are templates for simple chairs, without substituents (e.g., Fig 1B), and for chairs showing all the substituents (e.g., Fig 2B). In either case, you can add, delete, or change things as you wish. Various kinds of stereo bonds (wedges and bars) are available by clicking the left-side tool button that is just below the regular C-C single bond button. It may have a wedge shown on it, but this will vary depending on how it has been used. To choose a type of stereo bond, click on the button and hold the mouse click; a new menu will appear to the right of the button.
The free drawing program Symyx Draw, the successor to ISIS/Draw, provides similar templates and tools. A basic chair structure is provided on the default template bar that is shown. More options are available by choosing the Rings template. See my page Symyx Draw for a general guide for getting started with this program.
The free drawing program ChemSketch provides similar templates and tools. To find the special templates for chairs, go to the Templates menu, choose Template Window, and then choose "Rings" from the drop-down menu near upper left. See my page ChemSketch for a general guide for getting started with this program.
If you want to draw chair structures by hand (and if you are going on in organic chemistry, you should)... Be careful. The precise zigs and zags, and the angles of substituents are all important. Your textbook may offer you some hints for how to draw chairs. A short item in the Journal of Chemical Education offers a nice trick, showing how the chair can be thought of as consisting of an M and a W. The article is V Dragojlovic, A method for drawing the cyclohexane ring and its substituents. J Chem Educ 78:923, 7/01. (I thank M Farooq Wahab, Chemistry, Univ Karachi, for suggesting that this article be noted here.)
Aside from drawing the basic chair, the key points in adding substituents are:
- Axial groups alternate up and down, and are shown "vertical".
- Equatorial groups are approximately horizontal, but actually somewhat distorted from that, so that the angle from the axial group is a bit more than a right angle -- reflecting the common 109 degree bond angle.
- As cautioned before, it is usually easier to draw and see what is happening at the four corners of the chair than at the two middle positions. Try to use the corners as much as possible.
Because axial bonds are parallel to each other, substituents larger than hydrogen generally suffer greater steric crowding when they are oriented axial rather than equatorial. Consequently, substituted cyclohexanes will preferentially adopt conformations in which the larger substituents assume equatorial orientation.

When the methyl group in the structure above occupies an axial position it suffers steric crowding by the two axial hydrogens located on the same side of the ring.

The conformation in which the methyl group is equatorial is more stable, and thus the equilibrium lies in this direction