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Conformations and Cycloalkanes

By James Ashenhurst

How To Draw The Cyclohexane Chair Conformation

Last updated: January 11th, 2023 |

How To Easily Draw Your First Cyclohexane Chair Using the “Parallelogram Technique”

Now that we’ve had an aerial tour of the cyclohexane chair, we’re going to move on to a very important skill: how to properly draw one of these beasties.

There are several techniques for properly draw a cyclohexane chair.

In this video, I walk through what I consider to be the most completely idiot-proof way to draw a chair, by first drawing a parallelogram (something you should already know how to do). Using this as the “base” of our chair, we then draw flaps moving up and down (representing the head and footrest), then put in the axial and equatorial groups.

Importantly, we can use this method to draw a chair in either the “left hand” or the “right hand” version of a cyclohexane chair, which becomes important, once we learn about chair flips (that’s next!)

In time and with a little bit of practice, you won’t need to draw the parallelogram to guide you. Think of it as a set of training wheels that you will later discard once you don’t need them anymore.

How NOT To Draw The Cyclohexane Chair Conformation: 4 Examples

Having an easy-to-remember technique is crucial.

Otherwise, your first few attempts in drawing a cyclohexane chair from memory might see you end up with one of these “variations” from a rogue’s gallery of 4 ways to screw up drawing a cyclohexane chair (and don’t feel bad – we’ve all done it . The trick is to make all the necessary mistakes before you take your midterm).

Bad Cyclohexane Chair #1: Crow’s Foot

crows foot cyclohexane how not dto draw a chair bond angles are not tetrahedral What’s wrong?  The axial and equatorial positions on the circled carbon are drawn in the wrong direction, leading to the carbon having a “crow’s foot” appearance. Bond angles in this carbon is not properly tetrahedral – furthermore, the adjacent carbons are eclipsed, not staggered!

How to fix: Flip the groups on the carbon. The “axial down” group should be drawn as “axial up” and the “equatorial up” group should be drawn as “equatorial down”. Remember, the axial groups alternate “up, down, up, down, up down” throughout the ring.

Bad Cyclkohexane  Chair #2: Crow’s Foot (slight return)

how not to draw a cyclohexane crows foot switched axial and equatorial What’s wrong? Another crow’s foot, although drawn on the “head rest” of the chair.

How to fix: switch “axial down” to “axial up” and “equatorial up” to “equatorial down”. Then you’ll see that your axial groups now alternate up down up down up down again (like they should)

Bad Cyclohexane Chair #3: “The Lightning Bolt” [h/t Chemjobber]

how not to draw a cyclohexane chair lightning bolt too thin What’s wrong? The axial and equatorial positions are drawn in properly, but the chair is drawn so thinly that the front carbons obscure the groups on the back carbons.

How to fix:  The angles at the “headrest” and “footrest” are too acute; open them up a bit. Also, stagger the two front carbons and the two back carbons so that they’re not directly in front of each other.

Bad Cyclohexane Chair #4: “Mr. Fatty”

how not to draw a cyclohexane chair mister fatty improper dimensions What’s wrong? Though all the axial and equatorial positions are drawn properly, this diagram strains the imagination for a cyclohexane supposedly consisting of six equal sides.

How to fix: Pretty straightforward – just don’t draw the vertical bonds so long!

 

 

00 General Chemistry Review
01 Bonding, Structure, and Resonance
02 Acid Base Reactions
03 Alkanes and Nomenclature
04 Conformations and Cycloalkanes
05 A Primer On Organic Reactions
06 Free Radical Reactions
07 Stereochemistry and Chirality
08 Substitution Reactions
09 Elimination Reactions
10 Rearrangements
11 SN1/SN2/E1/E2 Decision
12 Alkene Reactions
13 Alkyne Reactions
14 Alcohols, Epoxides and Ethers
15 Organometallics
16 Spectroscopy
17 Dienes and MO Theory
18 Aromaticity
19 Reactions of Aromatic Molecules
20 Aldehydes and Ketones
21 Carboxylic Acid Derivatives
22 Enols and Enolates
23 Amines
24 Carbohydrates
25 Fun and Miscellaneous
26 Organic Chemistry Tips and Tricks
27 Case Studies of Successful O-Chem Students

Comments

Comment section

9 thoughts on “How To Draw The Cyclohexane Chair Conformation”

  5. Aaaah! The equatorial H’s are pointing the wrong way on the two central carbons! (They should be parallel to the side C-C bonds). To all students — if you draw the equatorial positions like this, you WILL get points taken off.
    Best,
    An Organic Chemistry Professor

    Reply

  7. Aren’t you drawing your equatorial hydrogen wrong on the middle two carbons. I’m just learning, but other pictures and videos seem to be doing those hydrogen in the opposite direction…

    Reply

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