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WS13, CHEM 211, Dr. Poutsma 1

Worksheet 13
Part A: Disubstituted Cyclohexane Cont.
How do multiple substituents affect the stability of the conformations of cyclohexane?

Model 1: Converting Dash/Wedge Cyclohexane to a Chair Conformation

Follow the steps below to draw a chair conformation of the given dash/wedge cyclohexane.
Reminders:
1) The numbers provided on the dash/wedge structure go clockwise around the ring, thus, any
numbers added to the chair structure should go clockwise around the ring as well.
2) Dashed substituents in the dash/wedge cyclohexane should point down in the chair conformation
and wedged substituents should point up.

Questions
1. a) Choose a carbon in the chair structure to be carbon 1. It doesn’t matter which carbon you
choose!! Based on the location of 1, label carbons 2 and 3 in the chair structure.

b) On carbon 1 in the chair conformation, identify whether the equatorial or axial position is
pointing down and add the methyl group to the appropriate location.

c) Add the methyl group to the appropriate location on carbon 3.

d) Check your answer. Are the methyl groups still trans?

2. a) Draw the chair flip of the chair conformer you drew in 1. Note: the carbon furthest to the left in
the above chair structure becomes the carbon furthest to the left in the chair-flip conformer
below. The same goes for the carbon furthest to the right.

b) Check your answer. The methyl groups should still be trans and the methyl group on 1 should
be down, while the one on 3 is up.

c) Which conformer is more stable or are they the same energy? Explain your answer.

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Part B: Chirality
How can you tell if an object is chiral?

Model 2: Same or Not the Same

Two molecules are identical if models of the two molecules can be superimposed without breaking
any bonds.

Questions
3. Make two identical models of the following molecule and confirm that they can be superimposed
on one another as shown above. Use different colored atoms for each of the four substituents.
H
G = green atom
G C R B = blue atom
R = red atom
B
4. Switch any two atoms on one of your models (leave the other model unchanged). Is this new
model identical to your original model?

5. Which of the following words describe(s) the relationship between these two models?
(Circle more than one choice, if appropriate.)
a. identical (or conformers = can be made identical via
single bond rotation)
b. stereoisomers (same atom connectivity, but not
identical)
c. constitutional isomers (same formula, but different
atom connectivity)
d. mirror images (look like reflections of one another in
the mirror)

Model 3: Stereocenters
It turns out that there are two ways to arrange four different groups around a tetrahedral atom (usually
C), and that these two arrangements will be mirror images of each other. Such a carbon is often marked
with an *, and called a stereocenter because its presence generates two stereoisomers.

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Questions
6. There is one stereocenter in each molecule in Model 3. Mark this stereocenter with an *.

7. The figure below shows that the two possible stereoisomers of 2-chlorobutane are mirror images.

Cl H H Cl
H3C CH3
CH2 CH3 H3C CH2
A B
mirror
a) Make a model of 2-chlorobutane that looks like the stereoisomer on the left side, structure A
(Check your model by holding it up to the drawing. Use the green atom for chlorine).

b) Can you make your model look like the drawing on the right side without breaking any bonds?

8. You can transform your model of A into B by switching any two groups attached to the
stereocenter. One way to show this on paper is to change a wedge bond into a dash bond and vice
versa.

a) How can you tell that the H on the chiral carbon of the line representation of A is going into
the paper?

b) Switch two groups on your model of 2-chlorobutane and confirm that it looks like C and B.

c) B and C are identical; they are just drawn in different orientations. How can the drawing of C
be converted into the drawing of B (Use your model if necessary)?

Model 3: Chirality
Definitions:
chiral – not identical to its mirror image. This term describes a property (like “round”) and is applied
to a molecule
enantiomer – the mirror image of a chiral object or molecule. This term describes a relationship (like
“sister”) and is applied to a pair of molecules

Questions
9. Give an example of an everyday object that is….
a) not chiral (achiral, identical to its mirror image)

b) chiral

c) Describe the enantiomer of the chiral object you named in part b.

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10. There are two ways to draw the enantiomer of a molecule: 1) draw the mirror image of the
molecule OR 2) switch wedged bonds into dashed bonds and vice versa.
a) Draw the enantiomer of the chiral molecule below by drawing its mirror image.

OH
OH

b) Draw the enantiomer of the molecule above by switching any dashed and wedged bonds.

c) Confirm that the molecules you drew in a and b are identical to each other.

Exercises
Part A
1. Draw the two chair conformations for cis-1,4-dimethylcyclohexane. Which conformation would
you expect to be the most stable. Explain.

2. If two groups in a disubstituted cyclohexane are not the same, then it is more favorable to have the
largest group in an equatorial position. Draw a chair representation of…
a) cis-1-methyl-4-tert-butylcyclohexane in its most stable conformation.

b) trans-1-methyl-4-tert-butylcyclohexane in its most favorable conformation.

c) Explain which is lower in energy (more stable) the cis or the trans isomer.

3. Recommended problems: 4.29 and 4.57

Part B
1. T or F: A molecule with one chiral center is always chiral. If false, draw an example.

2. a) Identify the chiral center in each molecule below (Each only has one).

b) The molecules above are not shown in 3D. For each molecule, draw both enantiomers by
indicating the 3D spatial arrangements at the chiral centers using dashes and wedges.

3. Read sections 5.1-5.3, pages 230-231 (5.4) and pages 235-236 (5.4c) in Karty.

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