CHEM 31 Dr.

Spence

HOMEWORK PROBLEMS: STEREOCHEMISTRY

1. Draw the following compounds and indicate any stereocenters with a (*). For those that have chiral
centers, draw each enantiomer and label the configuration at each stereocenter (R or S).
2-chloropentane 3-methylhexane
3-chloropentane 2-methylhexane

2. Determine (R) or (S) configurations at all chiral centers in the following molecules.
OH OCH3 NH2 H

HO H CH3 Cl CF3
CF3 Br

OH
O HO CH3OH
O N
CH3 H

3. For each pair of molecules below indicate whether they are identical to each other or if they are
enantiomers of each other. For those that are identical, draw the enantiomer.
CH3 OCH3
CO2H OH
Cl CF3 F3C CH3
H3 C OH H CO2H
H H3 C OCH3 Cl

4. Consider the molecule 1-bromo-3-chlorocyclohexane and answer the following questions: (a) how
many chiral centers are present? (b) what is the maximum number of stereoisomers possible? (c) draw
all the possible stereoisomers and label them A, B, C etc. (draw them as a hexagon using wedge and
dash to indicate stereochemistry). (d) define the configuration at all chiral centers and describe the
relationship between all stereoisomers.

5. Draw all possible stereoisomers of the following compound. To make it easier, use Fischer
projections with the CH2OH on top and bottom in each drawing. Label the configuration at each chiral
center. Which of these compounds are chiral?
CH2OH
OH use this Fischer
projection

HO OH
OH OH
CH2OH

6. Given the following information about a hypothetical molecule, calculate the % optical purity of a
sample containing a mixture of the two enantiomers with an optical rotation [] of (a) +33.9º and (b) –
14.1º. For each of these mixtures also provide the relative % of each enantiomer (%R and %S).
a a
(-)-(R)-hypothetical (+)-(S)-hypothetical
[] = -37.6 d b b d [] = +37.6
c c
CHEM 31 Dr. Spence

7. For each pair of molecules below indicate if they are identical, enantiomers or diastereomers.
(2R,3R,4R,5R)-2,3,4,5-tetrachlorohexane and (2R,3R,4R,5S)-2,3,4,5-tetrachlorohexane

CH3 OH CH3 H3C

OH CH3 CH3 H3C

H H
H CH3 H3C CH3 H3 C Br Br CH3
H3 C Br Br H
H3 C H H H
H CH3

8. Draw all possible (stereoisomeric) products from each of the following reactions. Label the products
A, B, C, etc and describe the relationship between the possible products. Indicate which molecules are
chiral. Indicate if all products form in equal amounts or unequal amounts. If the product mixture is
expected to be optically active check the box in front of the reaction.

1. OsO4
2. NaHSO3

1. OsO4
2. NaHSO3

OH Br2

H2, Pd/C

Br
H3C HBr

9. While considering the cyclohexane ring as a planar hexagon, draw an optically active version of
1,2,3,4,5,6-hexachlorocyclohexane.

10. For the first compound in question 8, identify all pro-chiral sp2 carbons. Are you looking at the Re
face or Si face? For the last compound in question 8, identify all pro-R positions.
CHEM 31 Dr. Spence

11. Circle the chiral centers in the following compounds.

O
OH

HO
OH
HO

Cholesterol Prostaglandin E2

12. Label with a "*" all the chiral centers in the following molecules.

O CH3
N O
NHCO2CH3
CH3
O
H C C H
C C O

H3CSSS H OR H
O

calecheamicin cocaine

13. Identify the following pairs of compounds as enantiomers, diastereomers, or the same.

Br Br OH
OH

Br Br

HO

OH
CHEM 31 Dr. Spence

14. Identify the following pairs of compounds as enantiomers, diastereomers, constitutional isomers, or
the same.

a.
Br Br Br
Br

b.
HO

OH

15. Identify the stereocenters in the following molecules, and indicate whether they are R or S.

H NH2
OH
Cl
HO OH

H O

16. Using the tests for chirality we have learned, determine whether the following molecules are chiral.
For each chiral molecule, determine the configuration (R or S) of the chiral center(s) in the molecule.

Br O

OH
CH3 OH NH2

CH3 OH HO OH

CH3

17. Circle those molecules below that are chiral.

Cl OH

Cl

HO O Cl Cl CH3
Cl
CH3
CHEM 31 Dr. Spence

18. Name the compound below. Be sure to include R,S designations.

19. Determine the relationship between the following pairs of molecules: enantiomers, diastereomers,
identical, or structural isomers.

a.

Br Br

b.
NH2 NH2

NH2 NH2

c.
OH

HO

d.
OH OH OH OH

Br Br

e.
CH3 CH3

CH3 H 3C

f.

OH OH OH OH