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WS16, CHEM 211, Dr. Poutsma 1

Worksheet 16
Diastereomers
What is the relationship between non-superimposable isomers that are not mirror images?

Model 1: Diastereomers
Diastereomers are non-superimposable stereoisomers (i.e. have the same connectivity, but different
arrangement in space) and are NOT MIRROR IMAGES!!!
CH3 CH3 CH3 CH3
Br S Br Br S Br
S I I I I
R R
A Cl B Cl C Cl D Cl
mirror mirror

CH3 pancake CH3 pancake

flip flip
Br Br
I I
B Cl D
Cl

Questions
1. a) Are A and B superimposable?

b) Are A and B mirror images?

c) What is the exact relationship between A and B (one word)?

2. What is the exact relationship between C and D (one word)?

3. a) Are A and C completely superimposable?

b) Are A and C mirror images?

c) What is the exact relationship between A and C (one word)?

4. a) Are A and D completely superimposable?

b) Are A and D mirror images?

c) What is the exact relationship between A and D (one word)?

Model 2: Absolute Configuration and Diastereomers

The absolute configuration of a molecule is its designation as R or S. Review: for molecules with one
stereocenter, 1) one enantiomer will be R and the other will be S, 2) the enantiomer of one molecule
can be drawn as a mirror image or by switching the groups on the dash and wedge of the stereocenter.

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Questions
5. a) Mark each stereocenter in A, B, C, and D with a *.

b) Assign each unassigned stereocenter as R or S.

6. a) Are the carbons in A and B bonded to Br both R, both S or is one R and one S?

b) Are the carbons in A and B bonded to I both R, both S or is one R and one S?

c) What conclusion can you draw about the absolute configurations of enantiomers with multiple
stereocenters?

d) Do your assignments of R and S for C and D (enantiomers) agree with your statement in 6c? If
not, modify your statement to fit the data.

7. a) Are the carbons in A and C bonded to Br both R, both S or is one R and one S?

b) Are the carbons in A and C bonded to I both R, both S or is one R and one S?

c) What conclusion can you draw about the absolute configurations (R and S) of diastereomers?
(Recall that A and C are diastereomers)

d) Do your assignments of R and S for A and D (diastereomers) agree with your statement in 7c?
If not, modify your statement to fit the data.

8. The enantiomer of a molecule with multiple stereocenters can also be drawn two ways. The first
way is to draw the mirror image (A and large B in Model 1). Compare A and the pancake flip of B
(or C and the pancake flip of D) to describe the second way to draw the enantiomer of a molecule
with multiple stereocenters. .

9. Compare A to C and the pancake flip of D to describe a way to draw a diastereomer of a

molecule.

Model 3: The Number of Stereoisomers

A compound has 2n stereoisomers, where n is equal to the number of chiral centers. These
stereoisomers consist of 2n/2 pairs of enantiomers.

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Questions
10. a) How many stereoisomers does a compound with two chiral centers have?

b) How many pairs of enantiomers does this compound have?

c) Do your answers to 10a and 10b agree with the structures given in Model 1? Explain.

11. a) How many stereoisomers does a compound with three chiral centers have?

b) How many pairs of enantiomers does the compound have?

Model 4: Stereoisomers
Conformers – can be interconverted via single bond
rotation (that is, without breaking bonds).
Conformers are alternate representations of the
same molecule.

Constitutional Isomers – have the same molecular

formula but different atom connectivity.

Stereoisomers – have the same molecular formula

AND the same atom connectivity, but CANNOT be
superimposed or interconverted via single bond
rotation.

You cannot buy a bottle of “anti” butane or “gauche” butane because in any sample of butane at
normal temperatures, the molecules are rapidly interconverting among all possible conformations. You
can buy a bottle of cis-butene or trans-butene.

Questions
12. Indicate the relationship between each pair. Choose from stereoisomers, identical, conformers,
constitutional isomers, or different formulas. (Each term is used at least once.)

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End of Class Summary

A molecule with two chiral centers has four possible stereoisomers (R,R; S,S; R,S and S,R). Each
stereoisomer (A) will have one enantiomer (B) and two diastereomers (C & D). For the enantiomers,
both chiral centers will have opposite configuration names (i.e. S,S for A and R,R for B). For disaster-
eomers, only one chiral center will have the opposite configuration name (i.e. S,S for A and S,R for C).

Exercises
1. Identify the following pairs of molecules as identical, constitutional isomers, enantiomers or
diastereomers.
a) OH CH3 b)
H OH OH OH OH OH

HO H
OH CH2CH3

c) Br d)
Br OH OH
H H
HH Br H
H
H H Br

2. Draw structures for the following names.

a) (2R, 3S)-2-amino-3-pentanol

b) (1S, 3S)-1-bromo-3-methylcyclopentane

3. Draw all the possible stereoisomers for the following molecule.

Cl OH

CH3

4. Read sections 5.5, N3.1c and N3.1f in Karty. Recommended problems 5.39, 5.40, 5.46, N3.9 and
N3.17

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