Stereochemistry Worksheet Lab

Section #
TA Name

Student Name
Student ID

1. Label (by circling or marking with an asterisk) all the stereoisomers on the following molecules. Note: you
cannot label absolute configuration (R or S) on the given structures since there is no wedge/dash scheme.
HN
B.

A.
H
N

F3C
Cl
Fluoxetine

Cl
HO

Setraline

C.

O
HO
O

F
O
Triamcinolone acetonide

2. Label the following compounds as having R or S configuration around the stereocenter(s).

HO H
1 2

Br
1
H

AcO H

H OH

1
H

H
Br

Br

OH

OTs

2
OH

F
Cl H

3. Give an example of:

a. A compound with two or more stereocenters that is superimposable on its mirror image.

b. A pair of compounds that are chiral but are non-superimposable and non-mirror images.

c. A pair of compounds with 2 or more stereocenters that are non-superimposable and mirror
images.

4. Draw the following compounds

a. (2S,5R)-5-chloro-2-ethylhexanoic acid

b. (1R,2R,4R)-4-ethylcyclohexane-1,2-diol

c. (2S,3R)-3-amino-2-phenylbutanal

d. (1S,2S,3R)-2-fluoro-3-propylcyclobutanol

e. (2E, 7Z)-5-bromo-2,7-nonadiene

5. For the following reactions:

a. Complete the reactions with both possible chiral products.
b. Determine and label the absolute configuration (R or S) of all stereocenters.
c. Label the reaction type and the stereochemical relationship (meso, enantiomer, diastereomer, or
none).
Starting
material

Reagents

Products

type

OsO4

H 2O

D2, Pd/C

MeOH

H 3O

Ph

HCl
Ether

OH

heat

Cl

Br2
CH2Cl
2

d. For reactions 5c through 5f, draw the reaction mechanism showing lone pairs, arrows, bond
making/breaking, etc. for each reaction.
3