Chair Cyclohexane Tutorial Page 1/4
1. Learn to draw a correct chair.
a. Start by drawing a 3C chain with a wider than usual bond angle.
b. Add parallel bonds to each side slanted approximately 20°.
c. Add a bond on the top left that is parallel to the bond on the bottom right.
d. Add the final bond on the top right that is parallel to the bond on the bottom left.
a b c d
The other chair conformation can be drawn by tilting the bonds in step "b" to 20° in the other direction.
b c d
Now you try drawing both ring flip conformations:
2. Be able to identify "up" carbons and "down" carbons.
If the two bonds of the ring attached to a carbon are pointing upward, the carbon is an "up" carbon.
If the two bonds of the ring attached to a carbon are pointing downward, the carbon is a "down" carbon.
"up" carbon "down" carbon
You Try: In each chair below, put a circle around every "up" carbon
and a triangle around every "down" carbon
3. Be able to draw in axial and equatorial substitutents on a chair
Start with axials: You Try: Draw in the axial substitutents
On every "up" carbon, the axial is pointed straight up. on the other chair conformation.
On every "down" carbon, the axial is pointed straight down.
Draw the "down"
axials on the
"down" carbons.
Draw the "up" axials
on the "up" carbons. notice the "break" in the bond
to indicate that it is behind the
front bond of the ring.
Chair Cyclohexane Tutorial Page 2/4
3. Be able to draw in axial and equatorial substitutents on a chair
Now for the equatorials.
On every "up" carbon, the equatorial is pointed down and to the side.
On every "down" carbon, the equatorial is pointed up and to the side.
Draw the “down” Draw the “up”
equatorials on the equatorials on the
"up" carbons. "down" carbons.
Ensure each equatorial is parallel with a Again, ensure each equatorial is parallel
bond of the ring! with a bond of the ring!
Drawing in all six equatorial bonds together: You Try: Draw in the equatorial substitutents
on the other chair conformation.
Notice: the three
equatorial bonds on the
left side point to the left,
and the three equatorial
bonds on the right side
Left Right point to the right.
4. Be able to put it all together.
You Try: In space below, draw both ring flip chair conformations. Then draw all six axial bonds and six
equatorial bonds on each. Finally draw in the twelve hydrogen on each axial and equatorial bond.
5. Be able to draw both chair conformations of mono-substituted cyclohexanes.
H Both are perfectly vaild chair conformations.
R If the group is “back,” translate it as a
“down” group on the ring. It may end up R
axial or equatorial depending on which H
carbon of the chair you place it on. On this carbon, R On this carbon,
the “down” group the “down” group
is equatorial. is axial.
You Try: Draw chair conformations for the molecule below putting the ethyl group at the indicated positions
on each chair.
Chair Cyclohexane Tutorial Page 3/4
6. Be able to draw a chair conformation containing two or more substituents.
CH3
a. Start by numbering b. Number your chair
1
your ring. This is just 6
2 Br in the same direction 5
Note: You can make any
6 1 carbon on the chair #1.
for bookkeeping, but (clockwise or Regardless of which one
you can use the 5 3 counterclockwise) as 3 you pick, you will still get a
4 4
IUPAC system if you the numbering in your 2 valid chair.
wish. Cl “flat” ring.
CH3
c. Draw in substituent 1 d. If the substituent is 1 “wedge” methyl = “up”
5 6 5 6
bonds on all a “wedge,” draw it in
numbered carbons 3 as an “up” substituent 3 Br “wedge” Br = “up”
containg a substituent. 4 2 4 2
on the chair. If it is a
“dash,” draw it as a Cl
“dash” Cl = “down”
“down” substituent.
e. Finish the chair by CH3 CH3
drawing in H’s on the
remaining substituent H
bonds. Alternatively, H Br or Br
erase these bonds to
leave the H’s implied. Cl H Cl
You Try: Draw valid chair structures for the molecule above using the alternative numbering positions on the
chairs below.
4 6 6 2 1
5 1 6
5
5 3
3 2 4 2
3 4
1
Note how I maintained a clockwise numbering in all cases because that is how I numbered the original chair.
You Try: Draw two valid chair conformations for each molecule shown below. Match the circled carbon to
the circled carbon in the chair.
OH Ph
Cl H 3C Br
7. Be able to determine the cis or trans relationship between two substituents on a chair cyclohexane.
On the carbons containing the substituents of interest imagine or draw a horizontal line.
-If the two substituents are both above the line or both below the line, they are cis.
-If one substituent is above the line and one is below the line, they are trans.
You Try: Identify each as cis or trans.
Cl Br Cl
Cl
Br CH3 CH3
Br
cis - both Cl and cis - both Cl and trans - Cl above Br
Br are above the Br are above the and Br below.
line. line. Cl
Chair Cyclohexane Tutorial Page 4/4
8. Be able to draw the ring flip conformation for a given chair containing multiple substituents.
a. Number the carbons b. Flip one side up and flip
on your chair. It may 5 6 the other side down to down 6 5
5 6
also be helpful to add 4 1
CH3 get the other chair 4 1 1
2 4
reference points (the 3 structure. 3 2 flip 3
2
red circle at C1 and the Br
up
blue circle at C4).
equatorial CH3
becomes axial
c. Place substituents. CH3
Keep them on the After a ring flip: 6 5
5 6
same numbered -Axial substituents become equatorial 4 1 1
-Equatorial substituents become axial 2 CH3 4
3
carbons. 3 2
Br Br
axial Br becomes equatorial
Some important things to note:
still “up” CH3 CH3
“up” CH3
CH3 CH3
The side bonds in each ring flip conformer Br still “down” trans Br still trans
are angled in opposite directions. Br “down” Br Br
The directionality (“up” or “down”) of cis/trans relationships should not change
groups does not change during a ring flip.
You Try: Draw the ring flip conformer for each chair below.
OH
Br F
H 3C Cl CH3
9. Be able to assess the relative stability of the two chair conformations for a given molecule.
-Having more groups equatorial increases stability. Bulky groups in the axial orientation suffer from
-Having bulkier groups equatorial increases stability. unfavorable 1,3-diaxial interactions.
*A ring flip can move a bulky group from the axial H CH3
orientation to the more stable equatorial orientation. H
The bulky axial methyl group is
“bumping” into the axial
Compare the ring flip conformations in the two hydrogen that are 3-carbons
examples below. away from the methyl.
CH3 Br Br CH3
H 3C
Cl
H 3C
A substituent
Increasing Bulkiness
OH
lower energy (more stable) lower energy (more stable) further down
both substituents equatorial the bulkier substituent is CH3 will have a
equatorial larger energy
cost
You Try: Draw the ring flip conformer and circle the one that is most stable. (instability)
associated
OH with the axial
orientation.
H 3C