Drawing the cyclohexane chair conformations adds unnecessary stress to most chemistry students. Follow the steps below to easily draw the chair conformation and ring flips like a pro so you can focus your mental energy on solving the reaction itself.
Step 1: Draw the cyclohexane chair conformation ring
Use the chair conformation stencil on The Pocket Chemist. Decide which ring flip you need to draw. The most traditional representation is drawn with the highest point at the top right which is drawn with the periodic table side of the pocket card facing up.
If you don’t have it yet, The Pocket Chemist is available for purchase for $11.50 with free shipping in the USA! It’s been endorsed by chemistry teachers, chemistry professors, professional chemists and organic chemistry tutors from around the country. It’s designed to help you quickly and neatly draw chemical reactions for both homework and professional work while also providing references for fundamental equations, physical constants and unit conversions in every-day chemistry.
While you wait for your Pocket Chemist to arrive (2-3 days), you can draw the rings like this:
Start with two parallel lines.
The upper line should be shifted to the left so that it halfway overlaps the lower line.
Imagine an isosceles triangle where the base connects the two nearest ends of each straight line.
Add a dot where the opposite point would go. Fill in the other two sides connecting the ends of the parallel lines to the point where the two new lines have approximately the same length as the existing parallel lines.
Repeat this for the other end to complete your hand-drawn chair conformation! If it looks a little sloppy, consider grabbing The Pocket Chemist above to draw quickly draw your chair and boat conformations, benzene rings bonding angles perfectly every time. Get the drawing done in a third of the time so you can focus on the difficult parts of the reactions.
Step 2: Draw the axial bonds
The axial bonds should go first. They alternate up and down at each carbon point. If you had The Pocket Chemist facing down (showing the periodic table), start by drawing an “up” bond at the top right corner and a “down” bond on the bottom left corner, with the lines exactly vertical. If you need to draw it with a ring flip (with the highest point on the left side) then flip over the molecule stencil. Finish by filling in alternating “up” and “down” axial bonds moving around the cyclohexane ring. You can use the straight edge of The Pocket Chemist to keep it extra clean.
Step 3: Draw the equatorial bonds:
Now add equatorial bond lines in the opposite direction (up or down) of each axial bond. Technically, these bonds are at 109 degrees from the axial bond. These should stick out of the plane and not be perfectly opposite the axial bonds nor at a perfect 90 degree angle. The easiest way to draw equatorial bonds on the chair conformation is to make them parallel to the cyclohexane ring line that is the second line moving clockwise or counter-clockwise around the ring from the carbon you’re drawing the equatorial bond on. This applies for all six equatorial bonds and in both cyclohexane ring flip variations!
Step 4: Add your molecules to the cyclohexane chair conformation.
When adding your molecules, it’s much easier to see details at the four corners. Avoid attaching complex molecules to the two middle carbons in the chair conformation. Remember that substituents larger than hydrogen begin to have steric crowding when they are axial on a chair conformation rather than equatorial. Substituted cyclohexanes will prefer more stable conformations where the larger substituents assume equatorial orientations.
Step 5: Draw a ring flip chair conformation (if required)
The ring flip chair conformation is mirrored across a line of your notebook paper (a horizontal line). If you have The Pocket Chemist, simply flip it over. You don’t need to worry about the rotation since it has rotational symmetry. The pointy ends before a ring flip stay pointy. However, axial bonds become equatorial bonds and equatorial bonds become axial. These changed bond types stay “up” if the started up, and down if they were down before the ring flip. Remember that axial bonds should be drawn vertically and equatorial should be neither vertical nor horizontal, approximately at 109 degrees and parallel to the 2nd line clockwise or counter-clockwise from the carbon you’re drawing the bond on.
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