MCAT and Organic Chemistry Study Guides, Videos, Cheat Sheets, tutoring and more

  • Tutoring
  • Organic Chem
    • Organic Chemistry Tutoring
    • Organic Chemistry Videos
    • Study Hall – Membership Site
  • MCAT
  • About
  • Contact
  • Tutoring
  • Organic Chem
    • Organic Chemistry Tutoring
    • Organic Chemistry Videos
    • Study Hall – Membership Site
  • MCAT
  • About
  • Contact

Drawing Chair Conformations and Ring Flips for Cyclohexane

October 3, 2014 By Leah4sci 96 Comments

Drawing chair conformations and ring flips for cyclohexaneStudying chair conformations is likely one of the trickiest visual topics in organic chemistry, perhaps second only to Fischer projections. Not only are you required to learn a 3-dimensional concept, but you also have to manipulate that 3-D molecule on 2-dimensional paper.

The average orgo student is not an artist, making this topic even trickier. In this article I'll show you a few quick and simple tricks to help you easily draw the standard hexagon, chair conformations and ring flips for cyclohexane.

When it comes to exams, you won't be graded on how ‘pretty' your chair looks. Instead your professor will look for clarity and the ability to distinguish your axial and equatorial substituents.

Drawing the Cyclohexane Hexagon

If there's one thing you learn in organic chemistry – it's how to draw a hexagon. Many students try to draw the entire thing at once, but the poor hexagon tends to look drunk and wobbly.

In fact, if you're starting to feel like the class is one big art lesson, read here: Organic Chemistry or Art Class?

Here's my approach:

  1. Draw 2 parallel lines
  2. Place a dot above the upper opening and another below the lower opening
  3. Connect the dots

drawing cyclohexane hexagon

Pretty? Not especially

But clear? Absolutely!

And that's what really matters.

As you get better you can combine steps 2 and 3 by simply visualizing the location of the dots.

Drawing the Cyclohexane Chair Conformation

bad chair conformation drawingThis is where the messiness and confusion arises. Most books will show a chair conformation slightly sideways, making it impossible to copy. Worse, it's really difficult to show which substituents are axial vs equatorial.

‘Bowties' as I like to call them, are ok for the computer generated chair conformation. Here is my simple version which my tutoring clients use on exams with great success.

Step 1:

Draw 2 parallel lines slightly offset from each other. Top left or top right will give you alternate chairs.

Step 2:

Place a dot above the upper opening, and another below the lower opening

Step 3:

Connect the dots

steps for drawing chair conformation cyclohexane

Kinda sounds like the directions for drawing a cyclohexane, doesn't it?

But the chair confirmation doesn't stop here. It's important to understand how to position your substituents. And even more important to show what is axial and what is equatorial.

So let's move on:

Step 4:

Identify the ‘up tip' OR ‘down tip' of your chair conformation, and draw a straight line up (up tip) or down (down tip) parallel to the y-plane. This is your first axial substituent.

drawing axial substituents on cyclohexane chair conformation

The chair conformation has alternating axial up, axial down… so once you have that single axial substituent move on to..

Step 5:

Alternate your axial substituents up and down all the way around your cyclohexane

Every carbon on the chair conformation has 1 substituent axial and the other equatorial. If axial is up equatorial is down, if equatorial is up then axial is down.

Step 6:

Pick any ONE carbon and locate its axial substituent. Draw the equatorial substituent up or down, the reverse of the axial substituent. But unlike the axial line, this one will start on the carbon and form a slight angle outward of the chair drawing. Do NOT draw these straight in the x or y plane.

drawing ring flip chair conformation cyclohexane

Adding substituents to your chair

This is my favorite part. I find students get so confused when they try to match the cyclohexane to the drawing.

I don't!

All I care about matching are the numbers.

Start with a blank chair conformation. Number the carbons in your cyclohexane and in your chair.

Clockwise or counterclockwise doesn't matter, as long as you use the same direction for both molecules.

converting hexagon to chair conformation

Then simply compare.

Identify the carbon number for the first substituent, if it's wedged add it to the up position.

If the substituent is dashed, add it to the down substituent (dashes down)

In using this trick you simply match the numbers and let your molecule quickly fall into place

drawing axial and equatorial chair conformation substituents

Drawing a Ring Flip

The logic and reasoning behind the chair conformation ring flip will be discussed in my upcoming chair conformations video series. (stay tuned) However, drawing the ring flip doesn't have to be as hard as students think.

Yes the flip happens when one molecule changes its conformation to another, but the key to drawing the flip successfully is to… Ignore the first chair!

Counter-intuitive, I know, but trust me this method works.

Once you have your first chair, determine if your parallel lines have upper right or upper left.

Draw another chair using the steps described above, but change the direction of your top line.

drawing ring flip for chair conformations

If your first chair has the upper line on the right, draw the second chair with the upper line left.

Ignore your first chair as you follow the rules for drawing and adding substituents.

Now for the fun part, determine the new location for the up-tip carbon by ‘pulling down' your ‘up-tip' or raising up your ‘down-tip' Number your new chair, and play ‘match the numbers'.

drawing ring flip with substituents for chair conformation

If there's a substituent up on carbon #1, it says up on carbon #1. If it's down it stays down.

The only thing that changes with your ring flip is the location of axial and equatorial.

Remember this:

Up stays up, down stays down

Axial becomes equatorial and equatorial becomes axial

cyclohexan chair conformation ring flip

Hopefully you've been drawing chairs as you read this article. What do you think? does the idea of drawing chair conformations and ring flips still sound as scary as it used to? Let me know by leaving a comment below

Watch the video below for a complete demonstration of what we learned above.

Ready to tackle some chair conformations? Learn about their structure, stability, flips and more in the Cyclohexane Chair Conformations Tutorial Video Series.

Would a Model Kit help you? Watch How to Use Your Organic Chemistry Model Kit.

After you've been through the tutorial, don't forget to test your understanding with the Chair Conformations Quiz!

Filed Under: Chair Conformations Tagged With: axial, chair conformations, chairs, cyclohexane, drawing chair conformations, drawing compounds, equatorial, hexagon, ring flip

Comments

  1. Chris says

    April 23, 2019 at 12:22 pm

    Hello! First of all, thank you so much for all these explanations and tips, itโ€™s really helpful and motivating! However I still donโ€™t get how we decide to put our equatorial substituents… Perhaps Iโ€™m stupid but I really donโ€™t get it.

    Reply
  2. hollysbeautyreviews says

    February 13, 2019 at 9:57 pm

    I struggled with drawing cyclohexanes with adding substituents for so long and this taught me in less than 5 minutes. Thank you so much!!

    Reply
  3. Baifern says

    February 3, 2019 at 9:38 pm

    Thanks a lot. You make me more understand about chair conformation. Iโ€™m thank you sooooooo muchhhh!

    Reply
  4. Lola says

    December 24, 2018 at 12:32 pm

    Thanks so much for this explanation! it helped me a lot!!

    Reply
  5. abbie says

    September 21, 2018 at 10:47 am

    When I learned chair structures when you do the flip and you “pull down” #2 the others flip up, so starting at #2 in the bottom right the one to the left would be #3 and the one in the bottom left corner would be #4. Same idea for the top numbers

    Reply
  6. Joseph says

    September 15, 2018 at 1:01 am

    This summary Rocks. Thanks!

    Reply
  7. ronald says

    September 13, 2018 at 11:58 am

    much understandable explaination madam

    Reply
  8. Andrew says

    July 30, 2018 at 2:12 pm

    You’re a good teacher. Thank you very much. Its clearer now.

    Reply
  9. ILLINDALA RAVI says

    June 27, 2018 at 12:44 pm

    Extremely helpful , i now have a clarity on chair conformations . ThankQ

    Reply
  10. Natalia Barria says

    June 20, 2018 at 3:30 am

    I found this to be very helpful! The one thing I got a little confused on was why you chose to put the #1 carbon on the lower right corner of the chair and then when you flipped it you put #1 in the middle. I understand that up stays up and down stays down but does it matter where you number the new chair?

    Reply
  11. Rahul Saxena says

    April 4, 2018 at 2:23 pm

    Thank you so much
    i cant even express how much you helped me out
    love from India

    Reply
  12. NADEEM MALICK says

    March 20, 2018 at 5:35 am

    Hi. Now i m still confuse after reading all this though it was quit a helpful. Why we use the CH3 group to assign its carbon #1? why don’t assign the #1 to any other carbon? is it necessary to assign it or we can assign #1 to any of the carbon?

    Reply
  13. Mashal says

    March 17, 2018 at 4:37 pm

    There’s no video? :-/

    Reply
  14. Sanjana says

    February 21, 2018 at 1:27 am

    That was by far the best explanation for the chair conformation that I have come across….thanks a lot …it really helped.

    Reply
  15. Dhruvanshu says

    February 19, 2018 at 11:50 pm

    Thank u. Itproved to be a great help.

    Reply
  16. Victoria Zebrowski says

    February 18, 2018 at 10:11 am

    this was really helpful! like the diagrams and labeling of everything. thanks!!

    Reply
  17. Kanchan says

    February 12, 2018 at 7:54 am

    Easiest way

    Reply
  18. kristy goelzer says

    January 17, 2018 at 4:24 pm

    Wow this was so helpful and informative. I wish I had this tutorial the first time I took this class.

    Reply
  19. Vishesh says

    December 8, 2017 at 11:47 am

    Thank you very much
    You really have simplified a thing that I never understood in classroom

    Reply
  20. Jeetu singh says

    December 3, 2017 at 1:29 pm

    How to show GI in two hexagon attached together

    Reply
  21. Rujeko Hither Mpambwa says

    November 27, 2017 at 10:37 am

    I benefited a lot mam thnx so much u r the best

    Reply
  22. Katrina says

    November 2, 2017 at 11:56 am

    Very very helpful!! Thank you so much for doing this!

    Reply
  23. Shona says

    October 30, 2017 at 6:34 pm

    I don’t usually leave comments, but this was the best and most thorough explanation of drawing chair conformations I have ever come across! Thank you, this was so very helpful! ๐Ÿ™‚

    Reply
  24. Dima says

    October 30, 2017 at 4:58 pm

    Hi I have a quick question, when doing a ring flip, how do you know which way to number the ring? I know you move it over one position, but does it matter if you go number #1 clockwise or counterclockwise? I understand that #1-6 have to go the same direction as the first chair conformation, but I can’t figure out how to start off the ring flip numbering. Thank you!

    Reply
  25. Alanazi says

    October 11, 2017 at 4:59 am

    thank you so much

    Reply
  26. cacimar rivera says

    September 22, 2017 at 10:17 pm

    wow, my fear of drawing these crazy flip rings
    went away, thank you

    Reply
  27. Pedro says

    September 15, 2017 at 2:27 pm

    Great post! Thank you.

    Reply
  28. Nidhi says

    September 1, 2017 at 11:31 am

    Helping me through my first semester of college Organic Chem! Thank you so much!!

    Reply
  29. praveen says

    July 9, 2017 at 9:21 am

    Oh my god…. Thanks lot……

    Reply
  30. Yaa says

    June 28, 2017 at 11:10 am

    Thank you for such clear and simple instructions!!

    Reply
  31. Parameswari says

    June 18, 2017 at 1:16 pm

    Thank you mam

    Reply
  32. mcacisi says

    June 6, 2017 at 10:28 am

    I am struggling to draw/identify cis and trans isomers in disubstituted cyclohane as chair confirmation, plz help

    Reply
  33. Dev christiano says

    May 29, 2017 at 6:32 am

    It was awesom specially that substituent part I was so confused thank u so much ……rocking…. Yeah

    Reply
  34. sarah says

    May 14, 2017 at 3:29 pm

    My prof showed your cyclohexane chair conformation video in our lecture and it was really helpful for everyone. Thank you very much!!!!

    Reply
  35. Samindri Malalagama says

    March 20, 2017 at 7:59 am

    It was very valuable.. Thanks alot..

    Reply
  36. leina says

    March 18, 2017 at 10:37 am

    You are the best!

    Reply
  37. ABDUR RAHMAN says

    March 9, 2017 at 2:51 pm

    bundle of thanks for sharing these valuable informnation

    Reply
  38. syedasharifi says

    November 27, 2016 at 9:49 pm

    this is very helpful, thank you.

    Reply
    • Leah4sci says

      December 29, 2016 at 4:35 pm

      You’re welcome!!

      Reply
  39. ishan amrit says

    November 15, 2016 at 2:15 pm

    you are great great great i have become your fan(would love to receive an autograph) thanks mam and love u so much for this

    Reply
  40. Sashen Ruhunage says

    November 8, 2016 at 5:56 am

    Really helpful ma’am !!! Thank you!!

    Reply
    • Leah4sci says

      December 29, 2016 at 5:18 pm

      You’re welcome, Sashen!

      Reply
  41. Bรธรผ ฤŒhล™รฃ says

    October 14, 2016 at 8:19 am

    thank you so much .. now I can say that I understand chair conformations <3

    Reply
    • Leah4sci says

      December 29, 2016 at 5:43 pm

      Great to hear!!

      Reply
  42. Celeste Mapling says

    October 5, 2016 at 10:25 am

    Thank you so much! Do you have a video for this yet?

    Reply
  43. dharmesh says

    July 5, 2016 at 9:59 pm

    Mam you are just awesome it helped me a lot thank u very much I love you mam..

    Reply
    • Leah4sci says

      August 10, 2016 at 8:30 am

      Glad to help!

      Reply
  44. julia says

    June 25, 2016 at 6:28 pm

    not sure if anyone posted this already (didn’t read through all the comments), but your equatorial markings on a few of the chairs on the ‘middle’ interior carbons are directed in the wrong way…
    for example, on the very last flipped configurational drawing, carbon #1 & #4 equatorial lines should be leaning to the opposite direction.

    Reply
    • Leah4sci says

      July 3, 2016 at 10:55 am

      If you’re referring to the ones going straight forward or back then it actually doesn’t matter. In truth we’re trying to draw it exactly forward or back. But that wouldn’t show on paper, so we offset slightly to one side or the other. Similar to drawing a Newman Projection in eclipsed conformation. It’s directly behind but we offset to one side making it visible on paper

      Reply
      • julia says

        July 6, 2016 at 1:59 am

        my professor would mark that wrong LOL

        Reply
      • Satrajit says

        July 2, 2018 at 7:05 am

        I am sorry, but the equatorial substutuents mentioned here do not go straight forward or back. They go behind and forward in one particular oblique orientation, which maintains the tetrahedral geometry of the carbon(s) in question. A model will illustrate this beautifully. The adjacent equatorial bonds form a perfect ‘M’ or ‘W’ shape between themselves. So Julia was spot on in what she said.

        Reply
  45. Devni Yashara says

    June 2, 2016 at 5:28 am

    wow superb…thankyou.

    Reply
    • Leah4sci says

      June 10, 2016 at 3:11 pm

      You’re welcome Devni

      Reply
  46. Cameron Chakraverty says

    April 22, 2016 at 1:24 pm

    Thanks so much, this is so helpful! I’m still having a little trouble determining which chair confirmation should be lower energy, do you have any tips on that?

    Reply
    • Leah4sci says

      May 3, 2016 at 8:45 am

      Cameron: Compare substituents and make sure the higher energy or bulkier subs are equatorial

      Reply
    • Farza says

      February 3, 2017 at 10:54 am

      Which ever conformation has more equatorial bonds has lower energy, and therefore is more stable. And vice versa for more axial bonds.

      Reply
  47. shazly says

    April 14, 2016 at 9:47 am

    i want to ask fischer projection for (R)-1-bromo-1-chlorobutane. may you help me

    Reply
    • Leah4sci says

      April 16, 2016 at 11:25 am

      See my Fischer Projection series: leah4sci.com/fischer

      Reply
  48. HARNEET SINGH says

    March 20, 2016 at 2:08 pm

    Sir you are awesome.

    Reply
    • Leah4sci says

      April 4, 2016 at 5:58 pm

      Harneet: I assure you, I am not a Sir

      Reply
      • Swarnavo says

        September 4, 2016 at 12:19 am

        Thanks a lot ma’am. This was one of the confusing things in organic chemistry, but now it’s clear as crystal. ๐Ÿ˜› You’re great ma’am.

        Reply
        • Leah4sci says

          September 19, 2016 at 1:27 pm

          You’re welcome, Swarnavo! I’m happy to hear that!

          Reply
  49. Akshaya Krishnan says

    March 18, 2016 at 5:18 am

    U r awesome! ๐Ÿ˜€

    Reply
    • Leah4sci says

      April 4, 2016 at 5:45 pm

      Thanks Akshaya

      Reply
  50. Sarah says

    March 13, 2016 at 9:29 pm

    if my numbers were moving clockwise opposed to counterclockwise when i do the chair flip would my numbers all move one to the right instead?

    Reply
    • Leah4sci says

      April 4, 2016 at 5:49 pm

      Sarah: You can flip in any direction, but make sure clockwise remains clockwise and counterclockwise remains counterclockwise

      Reply
  51. Katherine Sanchez says

    February 19, 2016 at 10:38 pm

    Thank you thank you thank you!!!!

    Reply
    • Leah4sci says

      April 4, 2016 at 5:28 pm

      You’re very welcome Katherine

      Reply
  52. jj says

    October 8, 2015 at 12:16 pm

    THANK YOU SO MUCH! this is the most helpful explanation of a ring flip!

    Reply
    • Leah4sci says

      October 10, 2015 at 5:40 pm

      You are very welcome JJ. Glad to help

      Reply
      • Deniz Yarsuvat says

        March 29, 2016 at 11:55 am

        You just saved my organic chemistry grade.

        Reply
        • Leah4sci says

          April 4, 2016 at 5:54 pm

          Glad to help Deniz

          Reply
  53. Megan says

    September 27, 2015 at 10:37 pm

    I’m a little confused about the numbering. For the upper left chair do you always number the carbon in the bottom right corner 1? Does it matter which carbon is carbon 1 as long as you keep things consistent when you do the ring flip?

    Reply
    • Leah4sci says

      September 28, 2015 at 6:27 pm

      Doesn’t matter where you start since it’s a ring. The key is to remain consistent with clockwise and counterclockwise numbering

      Reply
  54. Mia says

    June 3, 2015 at 5:45 am

    you are amazing!!! actual life saver thank youuuuu!

    Reply
    • Leah4sci says

      June 3, 2015 at 11:27 am

      Thank you Mia ๐Ÿ™‚
      Glad to help

      Reply
  55. andrea ambor says

    May 12, 2015 at 8:40 pm

    I’m really sorry but I’m having trouble understanding why the numbers were moved on the last step…all the numbers in the cyclohexane seemed to move clockwise?

    Reply
    • Leah4sci says

      May 12, 2015 at 9:47 pm

      In a ring flip the corner carbon is pulled down and the entire numbering system shifts. But as long as you keep your sequence clockwise or counterclockwise (keep the same as the pre-flip chair) you’ll be ok

      Reply
  56. sach dev says

    March 21, 2015 at 8:27 pm

    Thank you so much Leah! ๐Ÿ™‚ this certainly cleared all my doubts! ๐Ÿ™‚

    Reply
    • Leah4sci says

      March 23, 2015 at 9:55 pm

      You’re welcome

      Reply
  57. Christina says

    February 24, 2015 at 10:13 pm

    do you have a tutorial on how to draw cis and trans confirmations?

    Reply
    • Leah4sci says

      February 25, 2015 at 11:31 pm

      Not at this time though I do cover it in my membership site at https://leah4sci.com/join

      Reply
  58. hakan says

    February 19, 2015 at 1:52 am

    Can you write chemical names

    Reply
    • Leah4sci says

      February 21, 2015 at 12:41 pm

      Chemical names for??

      Reply
  59. A says

    January 3, 2015 at 4:43 pm

    This is amazinggg and so helpful! Thank you so much!

    Reply
    • Leah4sci says

      January 4, 2015 at 3:23 pm

      You are very welcome

      Reply
  60. Hannah says

    December 14, 2014 at 11:44 pm

    Thank you thank you thank you! So helpful!

    Reply
    • Leah4sci says

      December 19, 2014 at 3:26 pm

      You are very welcome Hannah

      Reply
  61. Laz says

    December 9, 2014 at 7:54 pm

    does it matter how you number the cyclohexane before I draw it in the chair conformation

    Reply
    • Leah4sci says

      December 10, 2014 at 10:14 am

      It doesn’t matter Laz, so long as your consistent with your numbering in terms of clockwise or counterclockwise.

      Reply
  62. Banda Simon J says

    October 5, 2014 at 4:23 pm

    YOU TRICKS APPEAR EASY, CLEAR AND LESS CONFUSING.

    Reply
    • Leah4sci says

      October 6, 2014 at 1:12 pm

      Thank you Banda. So glad I can help. Drawing chairs should be fun not tricky

      Reply
  63. Jennifer says

    October 4, 2014 at 1:47 pm

    Why on the ring flip, you started putting your “1” in a different position?

    Reply
    • Leah4sci says

      October 4, 2014 at 11:56 pm

      Good question Jennifer. When you ring flip you have to pull the top carbon down. This moves every carbon over 1 position. So if the top carbon was 2, in the ring flip the bottom carbon will be 2. That means carbon 1 moved 1 position to the left in the drawing. Try this with your model kit and give every number a different color substituent

      Reply
      • Jennifer says

        October 5, 2014 at 2:49 am

        Thanks for your help! I now understand chair conformations! ๐Ÿ˜€

        Reply
        • Leah4sci says

          October 6, 2014 at 1:14 pm

          Thanks Jennifer – so glad I can help clarify this tricky topic

          Reply

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

3 Month MCAT Plan

What does a 3-month MCAT Study Plan entail? Click to Read/Download

3 month mcat study plan leah4sci

Can I help you find a topic?

Download my Free Organic Chemistry Cheat Sheets by clicking on the image below



MCAT Tutorials, Videos & More

MCAT Home Page
Scroll down for orgo resources
MCAT Math Without a Calculator
MCAT Physics
MCAT Chemistry
MCAT Biology
MCAT Biochemistry
MCAT CARS / Critical Reading
MCAT Resources, Tips & More

Organic Chemistry Tutorials & Videos

Orgo Syllabus Companion
- Gen Chem Foundation for Orgo
- Orgo Basics Foundation
- Resonance Structures
- Naming Organic Compounds
- Acids and Bases
- Newman Projections
- Chair Conformations
- Chirality and Stereochemistry
- Fischer Projections
- Intro to Mechanisms
- Alkene Reactions
- Alkyne Reactions
- Free Radical Reactions
- Substitution Elimination Reactions
- Diels Alder
- Aromaticity & Electrophilic Aromatic Substitution (EAS)
- Alcohols
- Oxidation and Reduction
- Acetal / Ketal
- Enolate Reactions
- Proton NMR Spectroscopy

Organic Chemistry Study Guide Cheat Sheets

2023 MCAT Test Dates

Click image below for test + score release dates and more

Radicals: Reactions, Stability Hybridization+

Click for New Tutorial: All about Free Radicals

Free Radicals in Organic Chemistry - Hybridization, Stability, Resonance, Reactions and Mechanism Videos

MCAT Students Come Work With Me

Work with me to figure out exactly what YOU need to ace your MCAT

Option 1: Strategy, tutorials, my help every step of the way in the MCAT Study Hall
[click for details]

Option 2 One-on-one Private MCAT Tutoring

Orgo Students: Come Work With Me

Work with me to ace your Organic Chemistry Course
Option 1: Join me for bimonthly live review/Q & A Sessions, 50+ Hours of Topic-Specific review/practice sessions, direct access to me and so much more... [click for details]

Option 2 One-on-one Private Tutoring

Organic Chemistry Reference Material and Cheat Sheets

Alkene Reactions Overview Cheat Sheet – Organic Chemistry

The true key to successful mastery of alkene reactions lies in practice practice practice. However, … [Read More...]

Click for additional cheat sheets

MCAT Tutorials

mcat math without a calculator 1 play

Introduction To MCAT Math Without A Calculator

While the pre-2015 MCAT only tests you on science and verbal, you are still required to perform … [Read More...]

Click for additional MCAT tutorials

Organic Chemistry Tutorial Videos

KET Keto enol tautomerization reaction and mechanism leah4sci

Keto Enol Tautomerization Reaction and Mechanism

Keto Enol Tautomerization or KET, is an organic chemistry reaction in which ketone and enol … [Read More...]

Click for additional orgo tutorial videos

Copyright ยฉ 2023 ยท Leah4Sci - All Rights Reserved. ยท Sitemap ยท Log in