Stereochemistry Exam Preparation Pack
24 Key Problem Types - Beginner / Intermediate
note - all problems can also be found here (link)
Section A: Assigning relationships Link to answer
[Link]
Decide if these molecules are enantiomers or diastereomers
based on the name alone.
1) (R)-Butan-2-ol and (S)-Butan-2-ol
2) (2R,3R)-2-Bromo-3-chlorobutane and (2S,3S)-2-Bromo-3-chlorobutane
3) (R,R)-Tartaric acid and (R,S)-Tartaric acid
4) (2R,4R)-2,3,4-Pentanetriol and (2S,4S)-2,3,4-Pentanetriol
5) (R,R,R,R,R)-BigComplicatedMoleculicine and
(R,R,R,R,S)-BigComplicatedMoleculicine
6) (E)-Hex-3-ene and (Z)-Hex-3-ene
7) (R,E)-4-Hexen-2-ol and (S,Z)-4-Hexen-2-ol
8) (R,E)-4-Hexen-2-ol and (R,Z)-4-Hexen-2-ol
9) (R,E)-4-Hexen-2-ol and (S,E)-4-Hexen-2-ol
10) (1R,2S)-1,2-Dimethylcyclohexane and (1S, 2R)-1,2-Dimethylcyclohexane
11) cis-1,2-Dimethylcyclohexane and trans-1,3-Dimethylcyclohexane
12) (R,S)-2,3-Dichlorobutane and (S,R)-2,3-Dichlorobutane
Stereochemistry Practice
Set - Beginner / Medium
1 [Link]
Section B: Assigning R/S
B-1 Assign all chiral centers as R or S [Link]
B-2 Assign all chiral centers as R or S [Link]
B-3 Assign R or S to all chiral centers [Link]
Stereochemistry Practice
Set - Beginner / Medium
2 [Link]
B-4 Assign R or S to the indicated chiral center in these Fischer projections
[Link]
B-5 Assign R or S to the chiral centers in these Sawhorse projections
[Link]
B-6 Assign R or S to the chiral centers in these Newman projections
[Link]
Stereochemistry Practice
Set - Beginner / Medium
3 [Link]
B-7 Assign R or S to the chiral centers in these cyclohexane chairs
[Link]
C-1 Are these chiral or achiral molecules? [Link]
C-2 Another set. Chiral or achiral molecules? [Link]
Stereochemistry Practice
Set - Beginner / Medium
4 [Link]
D-1 Decide if a molecule has chiral centers and if so, how many stereoisomers
each has. If there is a meso compound, draw the structure using wedge/dash
[Link]
2 chiral centers
4 stereoisomers
E-1 Decide if these molecules are enantiomers, diastereomers, the same, or
constitutional isomers [pssst - this is a very common class of exam problem!]
[Link]
Stereochemistry Practice
Set - Beginner / Medium
5 [Link]
E-2 Enantiomers, diastereomers, the same, or constitutional isomers?
[Link]
E-3 Enantiomers, diastereomers, the same, or constitutional isomers?
[Link]
E-4 Enantiomers, diastereomers, the same, or constitutional isomers?
[Link]
Stereochemistry Practice
Set - Beginner / Medium
6 [Link]
F-1 Convert each of these line drawings (“perspective” drawings) to a Fischer
projection. [Link]
G-1 Convert each of these Fischer projections to line drawings (use the template
below) [Link]
H-1 Convert each of these Newman projections to a Fischer projection.
[Link]
Stereochemistry Practice
Set - Beginner / Medium
7 [Link]
I-1 Given these names, draw the following molecules:
• (S)-2-Chlorobutane [Link]
• (2R,3R)-3-Chloropentan-2-ol
• (1R,2S)-2-Amino-1-phenylpropan-1-ol
J-1 The structure below is one enantiomer of the molecule Fucitol.
Draw the enantiomer of this molecule, which also goes by the name D-Fuc-ol.
[Link]
J-2 The structure below goes by the name Thebacon. How many chiral
centers does Thebacon have? For bonus points draw the enantiomer
using the template on the right. [Link]
Stereochemistry Practice
Set - Beginner / Medium
8 [Link]
J-3 The molecule below is known as Moronic acid. How many chiral centers does
it have? Try drawing the enantiomer using the template on the right.
[Link]
K-1 Optical rotation questions. [Link]
a) If the specific rotation of (+)-Fucitol is +50°, and the rotation of
a sample of Fucitol is measured to be –10°, what is the per-cent
composition of (+)-Fucitol and (–)-Fucitol in the sample?
b) A 5.0 mg sample of Thebacon is dissolved in 1.0 mL of methanol and the
solution placed in a cell with a 2.0 cm path length. The observed rotation
was +0.105°.
What is the [a]D for Thebacon?
L-1 [Assumes you have covered free-radical reactions of alkanes]
How many different monochlorinated isomers (including stereoiso-
mers) are possible for each of these molecules?
[Link]
Stereochemistry Practice
Set - Beginner / Medium
9 [Link]